Production Dynamics of Cyanopeptides by Microcystis Aeruginosa and Dolichospermum Flos-Aquae and Effects of Nutrient Availability

Production dynamics of cyanopeptides by Microcystis aeruginosa and Dolichospermum flos-aquae and effects of nutrient availability

Regiane Natumi1,, Elisabeth M.L. Janssen1*

1 Department of Environmental Chemistry, Swiss Federal Institute of Aquatic Science and Technology (Eawag), 8600 Dübendorf, Switzerland

Electronic Supplementary Information

The electronic supplementary information contains 49 pages numbered S1-S49, 13 figures, and 7 tables.

S 1 List of Tables

Table S1. Composition of modified WC growth medium (Guillard and Lorenzen, 1972)...... 5 Table S2. Standard analytical information including: absolute response factor (RF), relative response factor (RRF), matrix effect (ME) for Microcystis aeruginosa PCC7806 (PCC7806) and for Dolichospermum flos-aquae (Doli), limit of detection (LOD), limit of quantification (LOQ) and recovery from the SPE clean-up and concentration steps for all cyanopeptide for which a reference standard or bioreagent was available...... 7 Table S3. Relative response factor (RRF) to microcystin-LR and extraction method recovery in percent for the 10 most abundant cyanopeptides identified in extracts of Microcystis aeruginosa or Dolichospermum flos-aquae for which no reference standard or bioreagent was available...... 8 Table S4. Cyanopeptide suspect list with compound name, compound class, neutral molecular formula, and monoisotopic mass of M+H. The table is placed at the end of the document...... 8 Table S5. List of all tentatively identified cyanopeptides in cell extracts of Microcystis aeruginosa PCC7806. Only the peptides that could be classified as tentative candidate (level 3), probable structure (level 2) or confirmed structure (level 1) are reported...... 18 Table S6. List of all tentatively identified cyanopeptides in cell extracts of Dolichospermum flos-aquae. Only the peptides that could be classified as tentative candidate (level 3), probable structure (level 2) or confirmed structure (level 1) are reported...... 19 Table S7. Isobaric compound group name and individual compounds within each group with the same molecular formula...... 20

S 2 List of Figures

Figure S1. Correlation between optical density at 750nm and cell density (cells L-1) for three N:P conditions (N:P =2, N:P= 20, N:P= 40)...... 6 Figure S2. Comparison of intensity over m/z range for mass spectrometry fragmentation spectra between confirmed structures (Level 1) of microcystin- LR (top) and Microcystis aeruginosa biomass extract (bottom) in head to tail plots. The m/z value, the retention time (min) and the HCD collision energy are noted...... 9 Figure S3. Comparison of intensity over m/z range for mass spectrometry fragmentation spectra between confirmed structures (Level 1) of cyanopeptolin A (top) and Microcystis aeruginosa biomass extract (bottom) in head to tail plots. The m/z value, the retention time (min) and the HCD collision energy are noted...... 10 Figure S4. Comparison of intensity over m/z range for mass spectrometry fragmentation spectra between confirmed structures (Level 1) of cyanopeptolin D (top) and Microcystis aeruginosa biomass extract (bottom) in head to tail plots. The m/z value, the retention time (min) and the HCD collision energy are noted...... 11 Figure S5. Comparison of intensity over m/z range for mass spectrometry fragmentation spectra between confirmed structures (Level 1) of aerucyclamide A (top) and Microcystis aeruginosa biomass extract (bottom) in head to tail plots. The m/z value, the retention time (min) and the HCD collision energy are noted...... 12 Figure S6. Comparison of intensity over m/z range for mass spectrometry fragmentation spectra between confirmed structures (Level 1) of oscillamide Y (top) and Dolichospermum flos-aquae biomass extract (bottom) in head to tail plots. The m/z value, the retention time (min) and the HCD collision energy are noted...... 13 Figure S7. Comparison of intensity over m/z range for mass spectrometry fragmentation spectra between confirmed structures (Level 1) of Anabaenopeptin NZ857 (top) and Dolichospermum flos-aquae biomass extract (bottom) in head to tail plots. The m/z value, the retention time (min) and the HCD collision energy are noted. Both, Anabaenopeptin NZ857 and Oscillamide Y (see Figure S6), are isobaric compounds with the same m/z and RT. Here, the fragmentation spectrum of the biomass extract does not match with the fragmentation spectra of the bioreagent Anabaenopeptin NZ857 and we conclude that Anabaenopeptin NZ857 was not present at our samples...... 14 Figure S8. Comparison of intensity over m/z range for mass spectrometry fragmentation spectra between confirmed structures (Level 1) of anabaenopeptin A (top) and Dolichospermum flos-aquae biomass extract (bottom) in head to tail plots. The m/z value, the retention time (min) and the HCD collision energy are noted...... 15 Figure S9. Comparison of intensity over m/z range for mass spectrometry fragmentation spectra between confirmed structures (Level 1) of anabaenopeptin B (top) and Dolichospermum flos-aquae biomass extract (bottom) in head to tail plots. The m/z value, the retention time (min) and the HCD collision energy are noted.a Several CID and HCD collision energies were

S 3 tested (CID 30 and 35; HCD 10, 20, 30, 40 and 50), however a better mass spectrometry fragmentation spectra could not be obtained for this compound. 16 Figure S10. Comparison of intensity over m/z range for mass spectrometry fragmentation spectra between confirmed structures (Level 1) of microcystin- YR (top) and Dolichospermum flos-aquae biomass extract (bottom) in head to tail plots. The m/z value, the retention time (min) and the CID collision energy are noted...... 17 Figure S11. Non-normalized growth curve of Microcystis aeruginosa PCC7806 under different N:P ratios in the WC-Medium...... 21 Figure S12. Total cyanopeptide concentrations in µmol L-1 as cyanopeptide class equivalents relative to total cell abundance for the cyclamides (left), microcystins (middle), and cyanopeptolins (right). The slope represents the cyanopeptide production rate in fmol cell-1 and parameters of the linear regression are listed in the insert...... 22 Figure S13. Total cyanopeptide concentrations in µmol L-1 cyanopeptide class equivalent relative to total cell abundance over the growth curve for three nutrient conditions N:P 2, 20 and 40...... 23

S 4 Table S1. Composition of modified WC growth medium (Guillard and Lorenzen, 1972).

Components Control +P(x10) -P(:2) +P -P -N -N and –P -MN (mg L-1) (x3) (:100) (:100) (:100) (:100) N/P=20 N/P=2 N/P=40

K2HPO4.3H2O 11.4 114 5.7 34.2 0.114 11.4 0.114 11.4

NaNO3 85 85 85 85 85 0.85 0.85 85

CaCl2.2H2O 36.8 36.8 36.8 36.8 36.8 36.8 36.8 36.8

MgSO4.7H2O 37 37 37 37 37 37 37 0.37

NaHCO3 12.6 12.6 12.6 12.6 12.6 12.6 12.6 12.6

Na2EDTA 4.36 4.36 4.36 4.36 4.36 4.36 4.36 0.0436

FeCl3.6H2O 3.15 3.15 3.15 3.15 3.15 3.15 3.15 0.0315

CuSO4.5H2O 0.01 0.01 0.01 0.01 0.01 0.01 0.01 0.0001

ZnSO4.7H2O 0.022 0.022 0.022 0.022 0.022 0.022 0.022 0.00022

CoCl2.6H2O 0.01 0.01 0.01 0.01 0.01 0.01 0.01 0.0001

MnCl2.4H2O 0.18 0.18 0.18 0.18 0.18 0.18 0.18 0.0018

Na2MoO4.2H2O 0.006 0.006 0.006 0.006 0.006 0.006 0.006 0.00006

H3BO3 1.00 1.00 1.00 1.00 1.00 1.00 1.00 0.01

TES buffer 115 115 115 115 115 115 115 115

S 5 2.0E+09 8.0E+08 2.0E+09 N:P 2 N:P 20 N:P 40 1.6E+09

6.0E+08 1.5E+09

1 -

1.2E+09 1

s l

4.0E+08 s

l l

l 1.0E+09

c c 8.0E+08 c

2.0E+08 y = 2E+09x + 5E+07 5.0E+08 4.0E+08 y = 2E+09x + 2E+08 R² = 0.7676 y = 2E+09x + 2E+08 R² = 0.9012 R² = 0.7885 0.0E+00 0.0E+00 0.0E+00 0 0.25 0.5 0.75 1 0 0.1 0.2 0.3 0.4 0 0.2 0.4 0.6 0.8 O.D. (750nm) O.D. (750nm) O.D. (750nm)

Figure S1. Correlation between optical density at 750nm and cell density (cells L-1) for three N:P conditions (N:P =2, N:P= 20, N:P= 40).

S 6 Table S2. Standard analytical information including: absolute response factor (RF), relative response factor (RRF), matrix effect (ME) for Microcystis aeruginosa PCC7806 (PCC7806) and for Dolichospermum flos-aquae (Doli), limit of detection (LOD), limit of quantification (LOQ) and recovery from the SPE clean-up and concentration steps for all cyanopeptide for which a reference standard or bioreagent was available.

Cyanopeptide RF RRF (MCLR) ME PCC7806 (%) ME Doli (%) LOD (µg/L) LOQ µg/L) Recovery (%) Microcystin LR 2.34E+10 1 9.43 6.55 1.58 5.26 85.84 Microcystin LY 1.54E+10 0.66 4.78 4.35 1.43 4.76 65.61 Microcystin LF 1.18E+10 0.51 3.63 1.52 1.24 4.12 61.54 Microcystin LA 2.84E+10 1.22 3.83 2.28 1.35 4.50 69.45 Microcystin LW 1.81E+10 0.78 5.05 7.64 1.07 3.55 16.74 Microcystin YR 1.89E+10 0.81 6.50 9.38 1.70 5.65 68.69 Microcystin RR 5.44E+10 2.33 1.95 0.85 1.52 5.06 63.49 [D-Asp3,E-Dhb7]MC-RR 5.36E+10 2.29 2.87 1.39 1.65 5.49 n.a. Nodularin 3.72E+10 1.59 2.61 3.18 1.68 5.59 73.91 Anabaenopeptin A 1.63E+10 0.70 -3.14 -2.98 0.90 3.01 92.49 Anabaenopeptin B 2.59E+10 1.11 -4.61 7.03 1.60 3.87 n.a. Oscillamide Y 2.00E+10 0.09 4.50 -70.30 1.91 6.38 n.a. Cyanopeptolin A 1.02E+10 0.44 -10.22 8.71 1.33 4.43 30.15 Cyanopeptolin D 6.89E+09 0.29 -12.73 9.21 1.42 4.74 n.a.

Aerucyclamide Aa 3.96E+09 0.17 1.89 3.55 1.23 4.11 n.a. aNote that the factor for Aerucyclamide A can be overestimated as the stability of the available bioreagent was not as certain. For some compounds the recovery was not determined indicated as “not analyzed” = n.a.

S 7 Table S3. Relative response factor (RRF) to microcystin-LR and extraction method recovery in percent for the 10 most abundant cyanopeptides identified in extracts of Microcystis aeruginosa or Dolichospermum flos-aquae for which no reference standard or bioreagent was available. Cyanopeptide RRF (MCLR) Recovery (%)

Aerucyclamide C n.a. 61.04

Aerucyclamide D n.a. 42.57

Cyanopeptolin B n.a. 63.74

Cyanopeptolin C n.a. 61.97

Cyanopeptolin 963A n.a. 57.83

MC-LR-demethyl group 1.78±0.22 63.94

Anabaenopeptin group 2.55±0.31 53.85

E,B1,F,MM850

MC-HtyR groupc n.a. 52.80

[l-Ser7]MC-EE(OMe) groupc 0.36±0.04 63.11 n.a. = not analyzed

Table S4. Cyanopeptide suspect list with compound name, compound class, neutral molecular formula, and monoisotopic mass of M+H. The table is placed at the end of the document.

S 8

Figure S2. Comparison of intensity over m/z range for mass spectrometry fragmentation spectra between confirmed structures (Level 1) of microcystin-LR (top) and Microcystis aeruginosa biomass extract (bottom) in head to tail plots. The m/z value, the retention time (min) and the HCD collision energy are noted.

S 9

Figure S3. Comparison of intensity over m/z range for mass spectrometry fragmentation spectra between confirmed structures (Level 1) of cyanopeptolin A (top) and Microcystis aeruginosa biomass extract (bottom) in head to tail plots. The m/z value, the retention time (min) and the HCD collision energy are noted.

S 10

Figure S4. Comparison of intensity over m/z range for mass spectrometry fragmentation spectra between confirmed structures (Level 1) of cyanopeptolin D (top) and Microcystis aeruginosa biomass extract (bottom) in head to tail plots. The m/z value, the retention time (min) and the HCD collision energy are noted.

S 11

Figure S5. Comparison of intensity over m/z range for mass spectrometry fragmentation spectra between confirmed structures (Level 1) of aerucyclamide A (top) and Microcystis aeruginosa biomass extract (bottom) in head to tail plots. The m/z value, the retention time (min) and the HCD collision energy are noted.

S 12

Figure S6. Comparison of intensity over m/z range for mass spectrometry fragmentation spectra between confirmed structures (Level 1) of oscillamide Y (top) and Dolichospermum flos-aquae biomass extract (bottom) in head to tail plots. The m/z value, the retention time (min) and the HCD collision energy are noted.

S 13

Figure S7. Comparison of intensity over m/z range for mass spectrometry fragmentation spectra between confirmed structures (Level 1) of Anabaenopeptin NZ857 (top) and Dolichospermum flos-aquae biomass extract (bottom) in head to tail plots. The m/z value, the retention time (min) and the HCD collision energy are noted. Both, Anabaenopeptin NZ857 and Oscillamide Y (see Figure S6), are isobaric compounds with the same m/z and RT. Here, the fragmentation spectrum of the biomass extract does not match with the fragmentation spectra of the bioreagent Anabaenopeptin NZ857 and we conclude that Anabaenopeptin NZ857 was not present at our samples.

S 14

Figure S8. Comparison of intensity over m/z range for mass spectrometry fragmentation spectra between confirmed structures (Level 1) of anabaenopeptin A (top) and Dolichospermum flos-aquae biomass extract (bottom) in head to tail plots. The m/z value, the retention time (min) and the HCD collision energy are noted.

S 15

Figure S9. Comparison of intensity over m/z range for mass spectrometry fragmentation spectra between confirmed structures (Level 1) of anabaenopeptin B (top) and Dolichospermum flos-aquae biomass extract (bottom) in head to tail plots. The m/z value, the retention time (min) and the HCD collision energy are noted.a Several CID and HCD collision energies were tested (CID 30 and 35; HCD 10, 20, 30, 40 and 50), however a better mass spectrometry fragmentation spectra could not be obtained for this compound.

S 16

Figure S10. Comparison of intensity over m/z range for mass spectrometry fragmentation spectra between confirmed structures (Level 1) of microcystin-YR (top) and Dolichospermum flos-aquae biomass extract (bottom) in head to tail plots. The m/z value, the retention time (min) and the CID collision energy are noted.

S 17 Table S5. List of all tentatively identified cyanopeptides in cell extracts of Microcystis aeruginosa PCC7806. Only the peptides that could be classified as tentative candidate (level 3), probable structure (level 2) or confirmed structure (level 1) are reported.

Class-specific Microcystin-LR Reference standard or Confidence Cyanopeptide[reference] Molecular formula equivalentsa equivalentsb bioreagent used for Level mean  stdev (%) mean  stdev (%) quantification

1 Aerucyclamide A1 C24H34N6O4S2 43.4 10.0 32.8  9.1 Aerucyclamide A 3 Aerucyclamide C2 C24H32N6O5S 24.7  5.7 18.6  5.2 Aerucyclamide A 3 Aerucyclamide B3 C24H32N6O5S2 11.3  2.7 8.6  2.6 Aerucyclamide A 3 Aerucyclamide D2 C26H30N6O4S3 3.0  0.9 2.3  1.2 Aerucyclamide A total aerucyclamides 82.4  18.9 62.2  7.1 1 MC-LR4 C49H74N10O12 2.3  0.7 10.2  3.5 MC-LR 3 MC-LR-demethyl groupc C48H72N10O12 1.3  0.4 5.6  1.9 MC-LR total microcystins 3.5  1.0 15.8  8.0 1 Cyanopeptolin D5 C48H76N8O12 5.3  1.4 6.9  2.6 Cyanopeptolin D 1 Cyanopeptolin A 5 C46H71N10O12H 4.3  1.2 8.5  3.1 Cyanopeptolin A 3 Cyanopeptolin C5 C47H73N8O12H 2.6  0.8 3.4  1.7 Cyanopeptolin D 3 Cyanopeptolin B5 C46H71N8O12H 1.3  0.6 2.5  1.5 Cyanopeptolin A 3 Cyanopeptolin 963A6 C49H69N7O13 0.5  0.2 0.7  0.6 Cyanopeptolin D total cyanopeptolins 14.1  3.5 22.0  8.0 aQuantitative analysis based on selected positive ion chromatograms of the protonated peptides. Relative amounts of variants smaller than two percent of the total were not included. Quantification was based on class-equivalent (mol /mg dry weight of biomass).bQuantification was based on Microcystin-LR equivalentc isobaric compounds, see Table S7.dA compound was identified as: a) tentative candidate (Level 3) based on exact mass (< 5 ppm mass error), accurate isotopic pattern (idotp > 0.9), and in silico fragmentation data comparison; b) probable structures (Level 2) when unique fragments were observed or when retention time could be matched between samples from different cyanobacteria producing the same cyanopeptide; c) confirmed structures (Level 1) when reference standards or bioreagents were available.

S 18 Table S6. List of all tentatively identified cyanopeptides in cell extracts of Dolichospermum flos-aquae. Only the peptides that could be classified as tentative candidate (level 3), probable structure (level 2) or confirmed structure (level 1) are reported. Class-specific Microcystin-LR Reference standard Confidence Cyanopeptide[reference] Molecular equivalentsa equivalentsb or bioreagent used Level formula mean  stdev (%) mean  stdev (%) for quantification

1 Oscillamide Y 7 C45H59N7O10 83.3  23.3 33.2  8.3 Oscillamide Y 1 Anabaenopeptin A 8 C44H57N7O10 6.8  1.8 22.1  5.1 Anabaenopeptin A 3 Anabaenopeptin E groupc C42H62N10O9 1.9  0.4 9.9  1.7 Anabaenopeptin B 1 Anabaenopeptin B 9 C41H60N10O9 1.3  0.3 6.7  1.2 Anabaenopeptin B 3 Ferintoic acid B10 C47H60N8O9 0.3  < 0.1 1.1  0.2 Anabaenopeptin A 3 Anabaenopeptin 872 C46H61N7O10 0.1  <0.1 0.3  0.1 Anabaenopeptin A 3 Anabaenopeptin C11 C41H60 N8O9 0.1  <0.1 0.3  0.1 Anabaenopeptin B 3 Anabaenopeptin D12 C44H57 N7O9 0.1  <0.1 0.2  0.1 Anabaenopeptin A total aerucyclamides 93.91  23.4 73.7  8.8 1 MC-YR groupc C49H74N10O12 2.2  <0.1 8.1  1.5 MC-YR 3 MC-LR-demethyl groupc C48H72N10O12 1.4  <0.1 6.6 1.1 MC-LR 1 MC-LR 4 C48H76N8O12 0.7  0.1 3.2  0.6 MC-LR 3 MC-HtyR groupc, 13, 14 C46H71N10O12H 0.9  0.2 3.5  0.6 MC-YR 3 [I-Ser7]MC-EE(OMe) (Group)c C47H67N7O17 0.2  <0.1 2.7  0.5 MC-RR 3 MC-FR/MphR-dehydro (Group)c C52H72N10O12 0.2  <0.1 1.0  0.2 MC-LR 3 MC-LR_1008 (Group)c C50H76N10O12 0.1  <0.1 0.6  0.1 MC-LR 3 MC-MR15, 16 C48H72N10O12S 0.1  <0.1 0.2  0.1 MC-LR total microcystins 5.87  0.6 26.0  2.1 3 Micropeptin SF90917 C45H63N7O13 0.2  <0.1 0.4  0.2 Cyanopeptolin A total cyanopeptolins 0.2  <0.1 0.4  0.2 aQuantitat ive analysis based on selected positive ion chromatograms of the protonated peptides. Relative amounts of variants smaller than two percent of the total were not included. Quantification was based on class-equivalent (mol /mg dry weight of biomass).bQuantification was based in Microcystin-LR equivalentc isobaric compounds, see Table S7.dA compound was identified as: a) tentative candidate (Level 3) based on exact mass (< 5 ppm mass error), accurate isotopic pattern (idotp > 0.9), and in silico fragmentation data comparison; b) probable structures (Level 2) when unique fragments were observed or when retention time could be matched between samples from different cyanobacteria producing the same cyanopeptide; c) confirmed structures (Level 1) when reference standards or bioreagents were available.

S 19 Table S7. Isobaric compound group name and individual compounds within each group with the same molecular formula.

Cyanopeptide Cyanopeptide Molecular formula Group name

Anabaenopeptin E Anabaenopeptin E C42H62N10O9 Anabaenopeptin B1 Anabaenopeptin F Anabaenopeptin MM850 Anabaenopeptin DA850

MC-YR MC-YR C52H72N10O13 MC-RY Micropeptin 103 [D-Asp3, (E)-Dhb7]MC-HtyR [d-Asp3]MC-HtyR [Dha7]MC-HtyR [D-Asp3, (E)-Dhb7]MC-HtyR [D-Asp3,(Z)-Dhb7]MC-HtyR MC-LR-demethyl [d-Asp3 Dhb7]MC-LR C48H72N10O12 [d-Asp3 Dha7]MC-HilR [d-Asp3]MC-LR [Dha7]MC-LR [dmAdda5]MC-LR MC-HtyR MC-HtyR C53H74N10O13 [D-Glu(OMe)6]MC-YR [Asp3 MGlu6] MC-HtyR [I-Ser7]MC-EE(OMe) [I-Ser7]MC-EE(OMe) C47H67N7O17 [D-Asp3, Ser7]MC-E(OMe)E(OMe) MC-FR/MphR-dehydro MC-FR C52H72N10O12 [Asp3]MC‐HphR MC-LR_1008 [D-Glu(OCH3)6]MC-LR C50H76N10O12 [Mdhb7] MC-LR MC-HilR MC-LHar [Dhb7]MC-LHar [D-MeO-Glu6]MC-LR [MeAla1]MC-LR [Leu1, Asp3, DMAdda5]MC-LR

S 20

Figure S11. Non-normalized growth curve of Microcystis aeruginosa PCC7806 under different N:P ratios in the WC-Medium.

S 21 Cylamides Microcystins Cyanopeptolins 1.4 0.4 0.4 mM slope ± stdev mM slope ± stdev mM slope ± stdev -1 2 -1 2 -1 2

n P in amol cell (r ) P in amol cell (r ) P in amol cell (r )

) t

1 1.2 0.50 54.27 ±4.09 (0.95) 0.50 22.23 ±5.13 (0.63) 0.50 3.01 ±0.47 (0.82)

L t

0.05 275.62 ±41.33 (0.78) 0.05 39.85 ±5.10 (0.84) 0.05 82.17 ±14.98 (0.71) n

s 0.3 0.3 t e 1.0

n 0.025 173.25 ±29.45 (0.77) 0.025 25.10 ±2.54 (0.91) 0.025 62.82 ±7.95 (0.83)

i 0.8

d q

i 0.2 0.2

s 0.6

l 0.4

a o

y 0.1 0.1

µ a

( 0.2

o t 0.0 0.0 0.0 0.E+00 1.E+10 2.E+10 0.E+00 1.E+10 2.E+10 0.E+00 1.E+10 2.E+10 cell abundance (cells L-1) cell abundance (cells L-1) -1 cell abundance (cells L )

Figure S12. Total cyanopeptide concentrations in µmol L-1 as cyanopeptide class equivalents relative to total cell abundance for the cyclamides (left), microcystins (middle), and cyanopeptolins (right). The slope represents the cyanopeptide production rate in fmol cell-1 and parameters of the linear regression are listed in the insert.

S 22 0.10 1.2 0.50

N:P 2 N:P 20 N:P 40

)

1 -

a 1.0

r L

t 0.08 0.40

n c

e 0.8

o a

c 0.06 0.30

d q

i 0.6

s e

s 0.04 0.20

a l

o 0.4

c m

0.02 0.10 l

µ 0.2

(

o t 0.00 0.0 0.00 0 10 20 30 40 0 10 20 30 40 0 10 20 30 40 cell abundance (cells L-1) cell abundance (cells L-1) cell abundance (cells L-1)

Figure S13. Total cyanopeptide concentrations in µmol L-1 cyanopeptide class equivalent relative to total cell abundance over the growth curve for three nutrient conditions N:P 2, 20 and 40.

S 23 Table S4: Cyanopeptide suspect list with compound name, compound class, neutral molecular formula, and monoisotopic mass of M+H.

Molecular formula monoisotopic

Compound Name Class (neutral) mass [M+H]

Aeruginosin 298B Aeruginosin C24H35N3O6 462.26036

Aeruginosin EI461 Aeruginosin C24H35N3O6 462.26041

Aeruginosin DA495B Aeruginosin C24H34ClN3O6 496.22089

Aeruginosin DA495A Aeruginosin C27H33N3O6 496.24421

Aeruginosin DA511 Aeruginosin C27H33N3O7 512.23913

Aeruginosin 205 A/B - SO3 - Xyl Aeruginosin C29H43N6O4Cl 575.31071

Aeruginosin 298A Aeruginosin C30H48N6O7 605.36572

Aeruginosin LH606 Aeruginosin C29H43ClN6O6 607.30054

Aeruginosin 98A - Sulfat Aeruginosin C29H46ClN6O6 609.31674

Microcin SF608 Aeruginosin C32H44N6O6 609.33951

Aeruginosin A Aeruginosin C34H44N6O5 617.34459

Aeruginosin 89A/B - Sulfat Aeruginosin C30H46ClN6O7 637.31165

Aeruginosin KY642 Aeruginosin C29H44Cl2N6O6 643.27722

Aeruginosin GE642 Aeruginosin C29H44Cl2N6O6 643.27722

Aeruginosin 101-SO3 Aeruginosin C29H45Cl2N6O6 643.27776

Aeruginosin DA642 Aeruginosin C32H44ClN6O6 643.30160

Aeruginosin TR642 Aeruginosin C32H46N6O8 643.34499

Aeruginosin LH650A Aeruginosin C31H47ClN6O7 651.32675

Aeruginosin LH650B Aeruginosin C31H47ClN6O7 651.32675

Aeruginosin 98-C - SO3 Aeruginosin C29H46N6O6Br 653.26622

Aeruginosin 102 A/B - SO3 Aeruginosin C33H45N6O8 653.32989

Aeruginosin 98B Aeruginosin C29H46N6O9S 655.31197

Aeruginosin 672 Aeruginosin C29H44ClN6O8S 672.27026

Aeruginosin KB676 Aeruginosin C37H52N6O6 677.40211

Aeruginosin 103-A Aeruginosin C35H48N6O8 681.36064

Aeruginosin GE686 Aeruginosin C29H44BrClN6O6 687.22670

Aeruginosin 102+Cl-SO3 Aeruginosin C33H44ClN6O8 687.29092

S 24 Aeruginosin 98A Aeruginosin C29H45ClN6O9S 689.27300

Aeruginosin DA688 Aeruginosin C29H45ClN6O9S 689.27300

Aeruginosin 89A/B Aeruginosin C30H44ClN6O10S 717.26792

Aeruginosin 101 Aeruginosin C29H44Cl2N6O9S 723.23403

Aeruginosin DA722 Aeruginosin C29H44Cl2N6O9S 723.23403

Aeruginosin 722 Aeruginosin C32H43ClN6O9S 723.25735

Aeruginosin 205 A/B - SO3 Aeruginosin C34H53N6O9Cl 725.36353

Aeruginosin GE730 Aeruginosin C29H44Br2N6O6 731.17618

Aeruginosin 98C Aeruginosin C29H45N6O9SBr 733.22249

Aeruginosin 102A/B Aeruginosin C33H44N6O11S 733.28615

Aeruginosin GE766 Aeruginosin C29H44BrClN6O9S 767.18351

Aeruginosin 205A Aeruginosin C34H53N6O12SCl 805.32035

Aeruginosin 205B Aeruginosin C34H53N6O12SCl 805.32035

Aeruginosin GE810 Aeruginosin C29H44Br2N6O9S 811.13300

Aeruginosin 828A Aeruginosin C36H53ClN6O12S 829.32035

Aeruginosin 596A Aeruginosin C34H52Cl2N6O13S 855.27629

Aeruginosin 596B Aeruginosin C34H52Cl2N6O13S 855.27629

Aeruginosin 865 Aeruginosin C41H64N6O14 865.45533

Anabaenopeptin I Anabaenopeptin C38H61N7O9 760.46035

Schizopeptin 791 Anabaenopeptin C42H61N7O8 791.45816

Anabaenopeptin J Anabaenopeptin C41H59N7O9 794.44470

Anabaenopeptin C Anabaenopeptin C41H60N8O9 809.45560

Anabaenopeptin 820 Anabaenopeptin C41H60N10O8 821.46684

Anabaenopeptin MM823 Anabaenopeptin C41H57N7O11 824.41888

Anabaenopeptin NZ825 Anabaenopeptin C45H59N7O8 826.44979

Anabaenopeptin D Anabaenopeptin C44H57N7O9 828.42905

Anabaenopeptin B Anabaenopeptin C41H60N10O9 837.46175

Anabaenopeptin NZ841 Anabaenopeptin C45H59N7O9 842.44470

Anabaenopeptin A Anabaenopeptin C44H57N7O10 844.42397

Anabaenopeptin E Anabaenopeptin C42H62N10O9 851.47740

Anabaenopeptin B1 Anabaenopeptin C42H62N10O9 851.47740

S 25 Anabaenopeptin F Anabaenopeptin C42H62N10O9 851.47740

Anabaenopeptin DA850 Anabaenopeptin C42H62N10O9 851.47740

Anabaenopeptin MM850 Anabaenopeptin C42H62N10O9 851.47740

Anabaenopeptin 856 Anabaenopeptin C46H61N7O9 856.46035

Oscillamide Y Anabaenopeptin C45H59N7O10 858.43962

Anabaenopeptin NZ857 Anabaenopeptin C45H59N7O10 858.43962

Mozamide A Anabaenopeptin C45H64N8O9 861.48690

Anabaenopeptin F1 Anabaenopeptin C43H64N10O9 865.49305

Anabaenopeptin T Anabaenopeptin C45H67N7O10 866.50222

Ferintoic acid A Anabaenopeptin C46H58N8O9 867.43995

Oscillamide B Anabaenopeptin C41H60N10O9S 869.43382

Anabaenopeptin 872 Anabaenopeptin C46H61N7O10 872.45527

Mozamide B Anabaenopeptin C46H66N8O9 875.50306

Ferintoic acid B Anabaenopeptin C47H60N8O9 881.45560

Anabaenopeptin HU892 Anabaenopeptin C45H68N10O9 893.52435

Anabaenopeptin KB899 Anabaenopeptin C48H65N7O10 900.48657

Anabaenopeptin KB906 Anabaenopeptin C46H70N10O9 907.54000

Anabaenopeptin 908 Anabaenopeptin C45H68N10O10 909.51927

Nodulapeptin B Anabaenopeptin C44H63N7O12S 914.43282

Anabaenopeptin MM913 Anabaenopeptin C49H67N7O10 914.50222

Anabaenopeptin 915 Anabaenopeptin C48H65N7O11 916.48148

Anabaenopeptin H Anabaenopeptin C46H70N10O10 923.53492

Nodulapeptin A Anabaenopeptin C44H63N7O13S 930.42773

Anabaenopeptin G Anabaenopeptin C49H67N7O11 930.49713

Oscillamide C Anabaenopeptin C49H68N10O10 957.51927

Cryptophycin 7 Cryptophycin C25H28ClNO6 474.16779

Cryptophycin 14 Cryptophycin C29H35ClN2O6 543.22564

Cryptophycin 12 Cryptophycin C29H35ClN2O7 559.22056

Cryptophycin 66 Cryptophycin C30H38ClN3O6 572.25219

Cryptophycin 6 Cryptophycin C30H37ClN2O7 573.23621

Cryptophycin 10 Cryptophycin C30H39ClN2O8 591.24677

S 26 Cryptophycin 43 Cryptophycin C34H42N2O7 591.30648

Cryptophycin 4 Cryptophycin C35H44N2O7 605.32213

Cryptophycin 24 Cryptophycin C34H42N2O8 607.30139

Cryptophycin 2 Cryptophycin C35H44N2O8 621.31704

Cryptophycin 17 Cryptophycin C34H41ClN2O7 625.26751

Cryptophycin 19 Cryptophycin C34H41ClN2O7 625.26751

Cryptophycin 28 Cryptophycin C34H41ClN2O7 625.26751

Cryptophycin 29 Cryptophycin C34H41ClN2O7 625.26751

Cryptophycin 49 Cryptophycin C34H41ClN2O7 625.26751

Cryptophycin 176 Cryptophycin C33H39ClN2O8 627.24677

Cryptophycin 18 Cryptophycin C35H43ClN2O7 639.28316

Cryptophycin 3 Cryptophycin C35H43N2O7Cl 639.28316

Cryptophycin 46 Cryptophycin C35H43ClN2O7 639.28316

Cryptophycin 16 Cryptophycin C34H41ClN2O8 641.26242

Cryptophycin 21 Cryptophycin C34H41ClN2O8 641.26242

Cryptophycin 40 Cryptophycin C34H41ClN2O8 641.26242

Cryptophycin 50 Cryptophycin C34H41ClN2O8 641.26242

Cryptophycin 29; 7b 8b-Epoxide Cryptophycin C34H41ClN2O8 641.26297

Cryptophycin 4; 6'-Chloro 7R* 8R*- Cryptophycin C34H41ClN2O8 641.26297 epoxide O-de-Me

Cryptophycin 51 Cryptophycin C36H45ClN2O7 653.29881

Cryptophycin 338 Cryptophycin C35H44ClN3O7 654.29405

Cryptophycin 337 Cryptophycin C35H44ClN3O7 654.29406

Cryptophycin 39 Cryptophycin C35H43ClN2O8 655.27807

Cryptophycin 77 Cryptophycin C35H43ClN2O8 655.27807

Cryptophycin 38 Cryptophycin C35H43ClN2O8 655.27807

Cryptophycin 1 Cryptophycin C35H43ClN2O8 655.27807

Cryptophycin 54 Cryptophycin C35H43ClN2O8 655.27807

Cryptophycin 327 Cryptophycin C35H43ClN2O8 655.27807

Cryptophycin 26 Cryptophycin C35H45ClN2O8 657.29372

Cryptophycin 30 Cryptophycin C35H45ClN2O8 657.29372

S 27 Cryptophycin 45 Cryptophycin C34H40Cl2N2O7 659.22798

Cryptophycin 292 Cryptophycin C36H45ClN2O8 669.29372

Cryptophycin 53 Cryptophycin C36H45ClN2O8 669.29372

Cryptophycin 52 Cryptophycin C36H45ClN2O8 669.29372

Cryptophycin 175 Cryptophycin C35H42Cl2N2O7 673.24419

Cryptophycin 15 Cryptophycin C35H45ClN2O9 673.28864

Cryptophycin 13 Cryptophycin C35H45ClN2O9 673.28864

Cryptophycin 23 Cryptophycin C34H40Cl2N2O8 675.22345

Cryptophycin 326 Cryptophycin C34H40Cl2N2O8 675.22345

Cryptophycin 63 Cryptophycin C34H42Cl2N2O8 677.23910

Cryptophycin 65 Cryptophycin C36H48ClN3O8 686.32027

Cryptophycin 9 Cryptophycin C36H47ClN2O9 687.30429

Cryptophycin 5 Cryptophycin C36H47ClN2O9 687.30429

Cryptophycin 31 Cryptophycin C35H42Cl2N2O8 689.23910

Cryptophycin 8 Cryptophycin C35H44Cl2N2O8 691.25475

Cryptophycin 296 Cryptophycin C36H46Cl2N2O8 705.27040

Cryptophycin 55 Cryptophycin C36H46Cl2N2O8 705.27040

Cryptophycin 25 Cryptophycin C35H44BrClN2O8 735.20423

Cryptophycin 309 Cryptophycin C38H49Cl2N3O9 762.29186

Micropeptin KT554 Cyanopeptolin C29H42N6O5 555.32895

Micropeptin KT608A/B Cyanopeptolin C32H44N6O6 609.33951

Micropeptin KT636 Cyanopeptolin C19H32N4O14S3 636.10717

Micropeptin KT650 Cyanopeptolin C34H46N6O7 651.35007

Tasipeptin B Cyanopeptolin C40H62N6O9 770.45783

Micropeptin MZ771 Cyanopeptolin C38H61N9O8 772.47159

Micropeptin MM836 Cyanopeptolin C43H60N6O11 837.43929

Planktopeptin BL843 Cyanopeptolin C41H61N7O12 843.43782

Micropeptin MZ925-SO3 (fragment) Cyanopeptolin C40H63N9O11 846.47198

Micropeptin MZ845 Cyanopeptolin C40H63N9O11 846.47198

Micropeptin MM850 Cyanopeptolin C44H62N6O11 851.45493

Micropeptin MZ859 Cyanopeptolin C41H65N9O11 860.48763

S 28 Tasipeptin A Cyanopeptolin C45H71N7O10 869.52624

Cyanopeptolin 880 Cyanopeptolin C45H64N6O12 881.46550

Micropeptin 88A Cyanopeptolin C44H65N7O12 884.47640

Micropeptin HU895A Cyanopeptolin C40H62ClN9O12 896.42792

Micropeptin HU895B Cyanopeptolin C40H62ClN9O12 896.42792

Micropeptin HU909 Cyanopeptolin C41H64ClN9O12 910.44357

Micropeptin SF909 Cyanopeptolin C45H63N7O13 910.45566

Micropeptin LH911A Cyanopeptolin C39H61N9O14S 912.41315

Micropeptin LH911B Cyanopeptolin C39H61N9O14S 912.41315

Micropeptin LH911C Cyanopeptolin C41H65N7O14S 912.43830

Micropeptin MM916 Cyanopeptolin C43H60N6O14S 917.39610

Somamide B Cyanopeptolin C46H62N8O12 919.45600

Nostopeptin BN920 Cyanopeptolin C46H64N8O12 921.47165

Micropeptin LH920 Cyanopeptolin C46H64N8O12 921.47165

Cyanopeptolin S Cyanopeptolin C40H63N9O14S 926.42879

Micropeptin MZ925 Cyanopeptolin C40H63N9O14S 926.42880

Micropeptin LH925 Cyanopeptolin C42H67N7O14S 926.45395

Nostopeptin B Cyanopeptolin C46H70N8O12 927.51860

Dolostatin 13 Cyanopeptolin C46H63N7O12 928.44269

Micropeptin KB928 Cyanopeptolin C44H68N10O12 929.50909

Cyanopeptolin B Cyanopeptolin C46H71N8O12H 929.53425

Micropeptin MM932 Cyanopeptolin C43H60N6O15S 933.39102

Micropeptin MZ1019 - SO3 Cyanopeptolin C41H65N9O14S 940.44445

Micropeptin MZ939A Cyanopeptolin C41H65N9O14S 940.44445

Micropeptin MZ939B Cyanopeptolin C41H65N9O14S 940.44445

Cyanopeptolin C Cyanopeptolin C47H73N8O12H 943.54990

Micropeptin SD944 Cyanopeptolin C46H72N8O13 945.52916

Cyanopeptolin 954 Cyanopeptolin C46H63N8O12Cl 955.43267

Nostopeptin A Cyanopeptolin C48H74N8O12 955.54990

Micropeptin KB956 Cyanopeptolin C46H72N10O12 957.54039

Cyanopeptolin A Cyanopeptolin C46H72N10O12 957.54039

S 29 Cyanopeptolin D Cyanopeptolin C48H76N8O12 957.56555

Micropeptin B Cyanopeptolin C47H74N8O13 959.54481

Micropeptin 90 Cyanopeptolin C42H59N9O15S 962.39241

Cyanopeptolin 960 Cyanopeptolin C45H64N6O15S 962.43014

Cyanopeptolin 963A Cyanopeptolin C49H69N7O13 964.50261

Micropeptin EI964 Cyanopeptolin C46H64N10O13 965.47271

Somamide A Cyanopeptolin C48H67N7O12S 966.46412

Micropeptin T20 Cyanopeptolin C46H59N6O15P 967.38488

Micropeptin KB970 Cyanopeptolin C47H74N10O12 971.55604

Anabaenopeptilide 90B Cyanopeptolin C45H61ClN8O14 973.40685

Micropeptin 973 Cyanopeptolin C41H64ClN9O14S 974.40547

Cyanopeptolin 973 Cyanopeptolin C46H72N10O13H 974.54313

Anabaenopeptilide 90A Cyanopeptolin C46H64N8O14 975.44342

Micropeptin 478A Cyanopeptolin C40H61ClN9O15S 976.38474

Micropeptin HU975 Cyanopeptolin C40H62ClN9O15S 976.38474

Micropeptin HM978 Cyanopeptolin C49H70N8O13 979.51351

Micropeptin MM978 Cyanopeptolin C49H70N8O13 979.51351

Micropeptin GH979 Cyanopeptolin C49H69N7O14 980.49753

Micropeptin SD979 Cyanopeptolin C49H69N7O14 980.49753

Scyptolin A Cyanopeptolin C45H69ClN8O14 981.46945

Micropeptin HA983 Cyanopeptolin C46H62ClN9O13 984.42284

Micropeptin KB984 Cyanopeptolin C48H76N10O12 985.57169

Micropeptin K139 Cyanopeptolin C47H74N10O13 987.55096

Cyanopeptolin 986 Cyanopeptolin C47H74N10O13 987.55147

Micropeptin A Cyanopeptolin C49H78N8O13 987.57611

Micropeptin HU989 Cyanopeptolin C41H64ClN9O15S 990.40039

Cyanopeptolin 992 Cyanopeptolin C48H68N10O13 993.50401

Micropeptin EI992 Cyanopeptolin C48H68N10O13 993.50401

Micropeptin KB992 Cyanopeptolin C50H72N8O13 993.52916

Micropeptin E Cyanopeptolin C50H71N7O14 994.51318

Micropeptin SF995 Cyanopeptolin C48H73N11O12 996.55129

S 30 Micropeptin KR998 Cyanopeptolin C51H66N8O13 999.48221

Micropeptin SD999 Cyanopeptolin C47H73N11O13 1000.54621

Micropeptin SD1002 Cyanopeptolin C51H70N8O13 1003.51351

Micropeptin KR1002 Cyanopeptolin C51H70N8O13 1003.51351

Cyanopeptolin SS Cyanopeptolin C40H63N9O17S2 1006.38562

Cyanopeptolin 1007 Cyanopeptolin C49H70N10O13 1007.51966

Micropeptin DR1006 Cyanopeptolin C51H74N8O13 1007.54481

Cyanopeptolin 1009 Cyanopeptolin C43H60ClN9O15S 1010.36909

Cl-Cyanopeptolin W Cyanopeptolin C47H65ClN10O13 1013.44939

Micropeptin T2 Cyanopeptolin C52H74N9O12 1016.54515

Micropeptin MZ1019 Cyanopeptolin C41H65N9O17S2 1020.40126

Micropeptin MZ1019 Cyanopeptolin C41H65N9O17S2 1020.40127

Cyanopeptolin 1020 Cyanopeptolin C50H72N10O13 1021.53531

Micropeptin HU1021 Cyanopeptolin C40H63N9O18S2 1022.38052

Micropeptin LH1021 Cyanopeptolin C50H71N9O14 1022.51933

Micropeptin F Cyanopeptolin C52H75N7O14 1022.54448

Aeruginopeptin 917SC Cyanopeptolin C51H74N8O14 1023.53973

Micropeptin C Cyanopeptolin C53H69N7O14 1028.49753

Micropeptin KR1030 Cyanopeptolin C53H74N8O13 1031.54481

Oscillapeptilide 97B Cyanopeptolin C52H73N9O13 1032.54006

Cyanopeptolin CB071 Cyanopeptolin C48H75ClN10O13 1035.52764

Cyanopeptolin 1034A/B Cyanopeptolin C51H74N10O13H 1036.55878

Cyanopeptolin 1040 Cyanopeptolin C51H73ClN8O13 1041.50584

Micropeptin HU1041 Cyanopeptolin C39H60ClN9O18S2 1042.32590

A90720A Cyanopeptolin C45H73N10O16S 1042.49995

Micropeptin KT1042 Cyanopeptolin C53H70N8O14 1043.50843

Aeruginopeptin 228A Cyanopeptolin C52H68N8O15 1045.48769

Micropeptin 103 Cyanopeptolin C52H72N10O13 1045.53531

Oscillapeptilide 97A Cyanopeptolin C53H75N9O13 1046.55571

Micropeptin KB1046 Cyanopeptolin C53H74N8O14 1047.53973

Aeruginopeptin 228B Cyanopeptolin C52H72N8O15 1049.51899

S 31 Micropeptin KB1048 Cyanopeptolin C49H77ClN10O13 1049.54329

Cyanopeptolin 1048 Cyanopeptolin C52H76N10O13 1049.56661

Micropeptin LH1048 Cyanopeptolin C52H76N10O13 1049.56661

Symplostatin 2 Cyanopeptolin C52H74N8O13S 1050.50961

Anabaenopeptilide 202A Cyanopeptolin C51H71N9O15 1050.51424

Micropeptin T1 Cyanopeptolin C55H71N8O13 1051.51351

Cyanopeptolin 1054 MB1 Cyanopeptolin C50H71ClN10O13 1055.49634

Cyanopeptolin 1054 MB2 Cyanopeptolin C52H75ClN8O13 1055.52149

Micropeptin 478B Cyanopeptolin C40H61ClN9O18S2 1056.34155

Micropeptin D Cyanopeptolin C55H73N7O14 1056.52883

Micropeptin DR1056 Cyanopeptolin C54H72N8O14 1057.52408

Micropeptin TR1058 Cyanopeptolin C53H70N8O15 1059.50334

Micropeptin DR1060 Cyanopeptolin C54H76N8O14 1061.55538

Planktopeptin BL1061 Cyanopeptolin C50H79N9NaO16 1061.56448

Oscillapeptin C Cyanopeptolin C55H79N7O14 1062.57578

Micropeptin 88N Cyanopeptolin C54H78N8O14 1063.57103

Micropeptin 88E Cyanopeptolin C54H78N8O14 1063.57103

Micropeptin LH1062 Cyanopeptolin C53H78N10O13 1063.58226

Cyanopeptolin 1068 Cyanopeptolin C53H77ClN8O13 1069.53714

Micropeptin HU1069 Cyanopeptolin C41H64ClN9O18S2 1070.35720

Anabaenopeptilide 202B Cyanopeptolin C50H68ClN9O15 1070.45962

Aeruginopeptin 917SA Cyanopeptolin C54H72N8O15 1073.51899

Microcystilide A Cyanopeptolin C54H72N8O15 1073.51899

Hofmannolin Cyanopeptolin C54H71N7O16 1074.50301

Aeruginopeptin 917SB Cyanopeptolin C54H76N8O15 1077.55029

Micropeptin 88B Cyanopeptolin C53H73N8O16 1078.52173

Micropeptin 88Y Cyanopeptolin C55H72N8O15 1085.51899

Oscillapeptin F Cyanopeptolin C51H76N8O16S 1089.51728

Oscillapeptin J Cyanopeptolin C47H68N10O18S 1093.45150

Micropeptin 1106 Cyanopeptolin C54H79N11O14 1106.58807

Oscillapeptin G Cyanopeptolin C53H77N9O17 1112.55102

S 32 Micropeptin 88C Cyanopeptolin C57H76N8O15 1113.55029

Nostocyclin Cyanopeptolin C56H76N8O16 1117.54520

Micropeptin 88D Cyanopeptolin C57H80N8O15 1117.58159

Micropeptin 1120 Cyanopeptolin C55H81N11O14 1120.60372

Scyptolin B Cyanopeptolin C52H80ClN9O16 1122.54843

Planktopeptin BL1125 Cyanopeptolin C54H79N9O17 1125.55939

Micropeptin 88F Cyanopeptolin C58H78N8O15 1127.56594

Oscillapeptin D Cyanopeptolin C54H77N7O17S 1128.51694

Oscillapeptin E Cyanopeptolin C55H75N7O17S 1138.50129

Aerugininopeptin 95A Cyanopeptolin C56H75N9O17 1146.53537

Aeruginopeptin 95B Cyanopeptolin C56H79N9O17 1150.56667

Oscillapeptin A Cyanopeptolin C56H77N7O18S 1168.51186

Oscillapeptin B Cyanopeptolin C57H79N7O18S 1182.52751

Aerucyclamide C Cyclamide C24H32N6O5S 517.22276

AerucyclamideC_Thiazoline Cyclamide C24H34N6O5S 519.23842

Banyascyclamide B Cyclamide C22H30N6O5S2 523.17919

Aerucyclamide B Cyclamide C24H32N6O4S2 533.19992

Aerucyclamide A Cyclamide C24H34N6O4S2 535.21557

Banyascyclamide A Cyclamide C25H26N6O4S2 539.15297

Raocyclamide A Cyclamide C27H30N6O5S 550.19984

Banyascyclamide C Cyclamide C25H28N6O5S2 557.16354

Raocyclamide B Cyclamide C27H32N6O6S 568.21040

Aerucyclamide D Cyclamide C26H30N6O4S3 587.15634

Obyanamide Cyclamide C30H41N5O6S 600.28503

Ulongamide F Cyclamide C30H49N5O6S 608.34763

Aerucyclamide D - SO2 Cyclamide C26H30N6O6S3 619.14617

Ulongamide A Cyclamide C32H45N5O6S 628.31633

Ulongamide B Cyclamide C32H45N5O7S 644.31125

Ulongamide D Cyclamide C34H49N5O7S 672.34255

Ulongamide E Cyclamide C35H51N5O7S 687.36602

Ulongamide C Cyclamide C36H45N5O7S 692.31125

S 33 Planktocyclin Cyclamide C39H60N8O8S 800.42548

Dolastatin 10 Cyclic C42H69N6O6S 786.50721 deoxy-Majusculamide D Cyclic C43H65N5O9 796.48551

Majusculamide D Cyclic C43H65N5O10 812.48042

Mirabimide B Microcolin C32H54N4O7 607.40653

Mirabimide C Microcolin C33H56N4O7 607.40653

Mirabimide A Microcolin C33H56N4O7 621.42218

Mirabimide D Microcolin C34H56N4O8 649.41709

Microcolin B Microcolin C39H65N5O8 732.49059

Microcolin A Microcolin C39H65N5O9 748.48551

[Asp3 Ser7]MC-mEmE Microcystin C48H67N7O8 870.51239

[Dha7]MC-EmE Microcystin C48H67N7O8 870.51239

[D‐Asp3, DMAdda5]MC‐LA Microcystin C44H63N7O12 882.46130

[D‐Asp3]MC‐VA Microcystin C44H63N7O12 882.46130

[D-Asp3] MC-LA Microcystin C45H65N7O12 896.47640

[Dha7] MC-LA Microcystin C45H65N7O12 896.47640

[DMAdda5]MC‐LA Microcystin C45H65N7O12 896.47695

MC‐VA Microcystin C45H65N7O12 896.47695

[Dha7]MC-LAbu Microcystin C46H67N7O12 910.49205

MC-LA Microcystin C46H67N7O12 910.49205

[Dha7]MC-LV Microcystin C47H69N7O12 924.50770

[d-Asp3]MC-LV Microcystin C47H69N7O12 924.50770

MC-LBu Microcystin C47H69N7O12 924.50770

MC-LAba Microcystin C47H69N7O12 924.50770

[D‐Asp3, D‐Glu(OMe)6]MC‐LAba Microcystin C47H69N7O12 924.50825

[Asp3]MC-FA Microcystin C48H63N7O12 930.46075

[Asp3, Dha7]MC‐YA Microcystin C47H61N7O13 932.44056

[Dha7]MC-LL Microcystin C48H71N7O12 938.52335

[d-Asp3]MC-LL Microcystin C48H71N7O12 938.52335

MC-LV Microcystin C48H71N7O12 938.52335

S 34 [Asp3]MC-RA Microcystin C45H66N10O12 939.49345

[Dha7]MC-FAba Microcystin C49H65N7O12 944.47640

[d-Asp3]MC-FAba Microcystin C49H65N7O12 944.47640

MC-FA Microcystin C49H65N7O12 944.47640

[Mdha3] MC-LR Microcystin C48H72N10O10 949.55057

MC-LL Microcystin C49H73N7O12 952.53900

[d-Asp3]MC-LAbu Microcystin C46H68N10O12 953.50909

MC-AR Microcystin C46H68N10O12 953.50909

[Asp3]MC-RAba Microcystin C46H68N10O12 953.50910

MC-RA Microcystin C46H68N10O12 953.50910

[Dha7]MC-LM Microcystin C47H69N7O12S 956.47977

[d-Asp3]MC-LM Microcystin C47H69N7O12S 956.47977

MC-FAba Microcystin C50H67N7O12 958.49205

MC-YA Microcystin C49H65N7O13 960.47131

[d-Asp3 Dha7]MC-LR Microcystin C47H70N10O12 967.52474

MC-RAba Microcystin C47H70N10O12 967.52475

MC‐AHar Microcystin C47H70N10O12 967.52529

[D‐Asp3, DMAdda5]MC‐LR Microcystin C47H70N10O12 967.52529

[Asp3, DMAdda5, Dhb7]MC‐LR Microcystin C47H70N10O12 967.52529

[Gly1, Asp3, Dhb7]MC‐LR Microcystin C47H70N10O12 967.52529

[Asp3]MC-HarAba Microcystin C47H70N10O12 967.52529

[Dha7]MC-WA Microcystin C50H64N8O12 969.47165

[Asp3]MC-WA Microcystin C50H64N8O12 969.47165

[D-Asp3, Dha7]MC-EE(OMe) Microcystin C46H63N7O16 970.44041

MC-LM Microcystin C48H71N7O12S 970.49542

MC-VF Microcystin C51H69N7O12 971.50042

[Dha7]MC-LF Microcystin C51H69N7O12 972.50770

[Asp3]MC-LF Microcystin C51H69N7O12 972.50770

MC‐VF Microcystin C51H69N7O12 972.50825

MC-YAba Microcystin C50H67N7O13 974.48696

S 35 [Asp3, Dha7]MC‐LY Microcystin C50H67N7O13 974.48751

[D-Asp3, (E)-Dhb7]MC-LR Microcystin C48H72N10O12 981.54039

[d-Asp3 Dha7]MC-HilR Microcystin C48H72N10O12 981.54039

[Asp3]MC-LR Microcystin C48H72N10O12 981.54039

[Dha7]MC-LR Microcystin C48H72N10O12 981.54039

[dmAdda5]MC-LR Microcystin C48H72N10O12 981.54039

[D‐Asp3, (Z)‐Dhb7]MC‐LR Microcystin C48H72N10O12 981.54094

[Gly1, Asp3, Dhb7]MC‐LHar Microcystin C48H72N10O12 981.54094

MC‐RApa Microcystin C48H72N10O12 981.54094

MC-WA Microcystin C51H66N8O12 983.48730

[Ser1, D‐Asp3, Dha7]MC‐LR Microcystin C47H70N10O13 983.52021

[d-Asp3 MAla7]MC-LR Microcystin C48H74N10O12 983.55604

[Dha7]MC-EE(OMe) Microcystin C47H65N7O16 984.45606

[D-Asp3, Dha7]MC-E(OMe)E(OMe) Microcystin C47H65N7O16 984.45606

[d-Asp3 Dha7]MC-MR Microcystin C46H68N10O12S 985.48116

[d-Asp3 l-Ser7]MC-LR Microcystin C47H72N10O13 985.53531

MC-LF Microcystin C52H71N7O12 986.52335

MC-FL Microcystin C52H71N7O12 986.52335

MC‐KynA (oxidized W) Microcystin C50H66N8O13 987.48276

[d-Asp3 l-Ser7]MC-EE(OMe) Microcystin C46H65N7O17 988.45097

[Asp3]MC‐LY Microcystin C51H69N7O13 988.50316

[Asp3, Dhb7]MC‐LY Microcystin C51H69N7O13 988.50316

[d-Asp3 Dha7]MC-YM Microcystin C49H65N7O13S 992.44338

[d-Asp3 ADMAdda5 Dha7] MC-LR Microcystin C48H70N10O13 995.51966

[Gly1, Asp3, ADMAdda5, Dhb7]MC‐LR Microcystin C48H70N10O13 995.52021

[D‐Asp3, ADMAdda5]MC‐VR Microcystin C48H70N10O13 995.52021

MC-LR Microcystin C49H74N10O12 995.55604

[6(Z)-Adda5]MC-LR Microcystin C49H74N10O12 995.55604

[d-Asp3]MC-HilR Microcystin C49H74N10O12 995.55604

S 36 [Dha7]MC-HilR Microcystin C49H74N10O12 995.55604

(E)-[Dhb7]MC-HilR Microcystin C49H74N10O12 995.55604

[Dha7]MC-LHar Microcystin C49H74N10O12 995.55604

[d-Asp3]MC-LHar Microcystin C49H74N10O12 995.55604

[D‐Asp3, D‐MeO-Glu6]MC‐LR Microcystin C49H74N10O12 995.55605

[Asp3, Dhb7]MC‐AhaR Microcystin C49H74N10O12 995.55659

[DMAdda5]MC‐HilR Microcystin C49H74N10O12 995.55659

[DMAdda5]MC‐LHar Microcystin C49H74N10O12 995.55659

MC‐RL Microcystin C49H74N10O12 995.55659

[d-Asp3 Dha7]MC-LW Microcystin C52H68N8O12 997.50295

MC-WAba Microcystin C52H68N8O12 997.50295

[MAla 7]MC-LR Microcystin C49H76N10O12 997.57169 dihydroMC-LR Microcystin C49H76N10O12 997.57169

[Dha7]MC-E(OMe)E(OMe) Microcystin C48H67N7O16 998.47171

MC‐OiaA (oxidised W) Microcystin C51H66N8O13 999.48276

[d-Asp3]MC-MR Microcystin C47H70N10O12S 999.49681

[Dha7]MC-MR Microcystin C47H70N10O12S 999.49681

[l-Ser7]MC-LR Microcystin C48H74N10O13 999.55096

[seco‐4/5][Asp3]MC‐LR Microcystin C48H74N10O13 999.55151

[Asp3, MeSer7]MC‐LR Microcystin C48H74N10O13 999.55151

MC‐LHph Microcystin C53H73N7O12 1000.53955

MC‐KynAba Microcystin C51H68N8O13 1001.49786

[D‐Asp3, Dha7]MC‐FR Microcystin C50H68N10O12 1001.50964

[L-Ser7]MC-EE(OMe) Microcystin C47H67N7O17 1002.46662

[D-Asp3, Ser7]MC-E(OMe)E(OMe) Microcystin C47H67N7O17 1002.46662

MC-LY Microcystin C52H71N7O13 1002.51826

[Asp3]MC‐HilY Microcystin C52H71N7O13 1002.51881

MC‐YL Microcystin C52H71N7O13 1002.51881

[d-Asp3]MC-YM Microcystin C50H67N7O13S 1006.45903

[Dha7]MC-YM Microcystin C50H67N7O13S 1006.45903

S 37 [Asp3, MSer7]MC‐LY Microcystin C51H71N7O14 1006.51373

[d-Asp3 ADMAdda5]MC- LR Microcystin C49H72N10O13 1009.53531

[ADMAdda5 Dha7]MC-LR Microcystin C49H72N10O13 1009.53531

[D‐Asp3, ADMAdda5, Dha7]MC‐HilR Microcystin C49H72N10O13 1009.53586

[Gly1, Asp3, ADMAdda5, Dhb7] MC‐ Microcystin C49H72N10O13 1009.53586 LHar

[Asp3, ADMAdda5, Dhb7]MC‐LR Microcystin C49H72N10O13 1009.53586

[D‐Glu(OCH3)6]MC‐LR Microcystin C50H76N10O12 1009.57169

[Mdhb7] MC-LR Microcystin C50H76N10O12 1009.57169

MC-HilR Microcystin C50H76N10O12 1009.57169

MC-LHar Microcystin C50H76N10O12 1009.57169

[Dhb7]MC-LHar Microcystin C50H76N10O12 1009.57169

[D-MeO-Glu6]MC-LR Microcystin C50H76N10O12 1009.57170

[MeAla1]MC‐LR Microcystin C50H76N10O12 1009.57224

[Leu1, Asp3, DMAdda5]MC‐LR Microcystin C50H76N10O12 1009.57224

[d-Asp3 Dha7]MC-RR Microcystin C47H71N13O12 1010.54179

[Asp3, DMAdda5,]MC‐RR Microcystin C47H71N13O12 1010.54234

[Gly1, Asp3, Dhb7]MC‐RR Microcystin C47H71N13O12 1010.54234

[d-Asp3]MC-LW Microcystin C53H70N8O12 1011.51860

[Asp3, (E)-Dhb7]MC-LW Microcystin C53H70N8O12 1011.51860

MC‐OiaAba (oxidised W) Microcystin C52H68N8O13 1013.49786

MC-MR Microcystin C48H72N10O12S 1013.51246

[d-Asp3 MSer7]MC-HilR Microcystin C49H76N10O13 1013.56661

[Ser7]MC-HilR Microcystin C49H76N10O13 1013.56661

[Ser7]MC-LHar Microcystin C49H76N10O13 1013.56661

[MSer7]MC-LR Microcystin C49H76N10O13 1013.56661

[mGlu6 Ser7]MC-LR Microcystin C49H76N10O13 1013.56661

[d-Asp3 MSer7]MC-HilR Microcystin C49H76N10O13 1013.56661

[Ser7]MC-HilR Microcystin C49H76N10O13 1013.56661

[Ser7]MC-LHar Microcystin C49H76N10O13 1013.56661

S 38 Acyclo‐LR: Adda‐D‐Glu(γ)‐Mdha‐D‐Ala‐ Microcystin C49H76N10O13 1013.56716 L‐Leu‐D‐MeAsp(β)‐L‐Arg‐OH

L‐Leu‐D‐MeAsp(β)‐L‐Arg‐Adda‐D‐ Microcystin C49H76N10O13 1013.56716 Glu(γ)‐Mdha‐D‐Ala‐OH

MC‐NfkA (oxidised W) Microcystin C51H66N8O14 1015.47767

[Asp3]MC‐M(O)R (oxidation artefact) Microcystin C47H70N10O13S 1015.49228

[d-Asp3] MC-FR Microcystin C51H70N10O12 1015.52474

[Dha7]MC-FR Microcystin C51H70N10O12 1015.52474

[D‐Asp3, Dha7]MC‐HphR Microcystin C51H70N10O12 1015.52529

[DMAdda5]MC‐FR Microcystin C51H70N10O12 1015.52529

[Asp3]MC‐RF Microcystin C51H70N10O12 1015.52529

[L-Ser7]MC-E(OMe)E(OMe) Microcystin C48H69N7O17 1016.48227

MC‐LHty Microcystin C53H73N7O13 1016.53446

[Asp3, Dha7]MC‐RY Microcystin C50H68N10O13 1017.50456

[Asp3, DMAdda5]MC‐RY Microcystin C50H68N10O13 1017.50456

MC-YM Microcystin C51H69N7O13S 1020.47468

[Dha7] MC-YM(O) Microcystin C50H67N7O14S 1022.45395

[d-Asp3] MC-YM(O) Microcystin C50H67N7O14S 1022.45395

[d-Asp3 ADMAdda5]MC-LHar Microcystin C50H74N10O13 1023.55096

[ADMAdda5]MC-LR Microcystin C50H74N10O13 1023.55096

[Leu1, Asp3]MC‐LR Microcystin C51H78N10O12 1023.58789

[Leu1, Dha7]MC‐LR Microcystin C51H78N10O12 1023.58789

[Val1]MC‐LR Microcystin C51H78N10O12 1023.58789

[d-Asp3]MC-RR Microcystin C48H73N13O12 1024.55744

[D-Asp3, (E)-Dhb7]MC-RR Microcystin C48H73N13O12 1024.55744

[Dha7]MC-RR Microcystin C48H73N13O12 1024.55744

[Gly1, Asp3, Dhb7]MC‐RHar Microcystin C48H73N13O12 1024.55799

MC-LW Microcystin C54H72N8O12 1025.53425

MC‐WL Microcystin C54H72N8O12 1025.53425

[MSer7]MC-HilR Microcystin C50H78N10O13 1027.58226

S 39 H‐L‐Hil‐MeAsp‐L‐Arg‐Adda‐D‐Glu‐ Microcystin C50H78N10O13 1027.58281 Mdha‐D‐Ala‐OH

MC‐NfkAba (oxidised W) Microcystin C52H68N8O14 1029.49278

MC-M(O)R Microcystin C48H72N10O13S 1029.50738

Monochloro-MC-LR Microcystin C49H73ClN10O12 1029.51707

[d-Asp3]MC-HphR Microcystin C52H72N10O12 1029.54039

[Dha7]MC-HphR Microcystin C52H72N10O12 1029.54039

MC-FR Microcystin C52H72N10O12 1029.54039

MC‐FR Microcystin C52H72N10O12 1029.54094

[Asp3]MC‐HphR Microcystin C52H72N10O12 1029.54094

Dihydroxy-MC-LR Microcystin C49H76N10O14 1029.56152

[Asp3]MC‐M(O2)R (oxidation artefact) Microcystin C47H70N10O14S 1031.48719

[d-Asp3 Dha7]MC-HtyR Microcystin C51H70N10O13 1031.51966

[d-Asp3]MC-YR Microcystin C51H70N10O13 1031.51966

[Dha7]MC-YR Microcystin C51H70N10O13 1031.51966

[dmAdda5]MC-YR Microcystin C51H70N10O13 1031.51966

[Asp3, DMAdda5]MC‐HtyR Microcystin C51H70N10O13 1031.52021

[Asp3]MC‐RY Microcystin C51H70N10O13 1031.52021

[Dha7]MC‐RY Microcystin C51H70N10O13 1031.52021

[Asp3, Dhb7]MC‐RY Microcystin C51H70N10O13 1031.52021

[Asp3, (E)‐Dhb7]MC‐YR Microcystin C51H70N10O13 1031.52021

MC‐LY(OMe) Microcystin C53H73N7O14 1032.52883

[Dha7] MC-(H4)YR Microcystin C51H74N10O13 1035.55096

[Asp3]MC(H4)YR Microcystin C51H74N10O13 1035.55096

[DMAdda5]MC‐(H4)YR Microcystin C51H74N10O13 1035.55151

MC-YM(O) Microcystin C51H69N7O14S 1036.46960

[ADMAdda]MC-LHar Microcystin C51H76N10O13 1037.56661

[ADMAdda5]MC‐HilR Microcystin C51H76N10O13 1037.56716

[d-Leu1]MC-LR Microcystin C52H80N10O12 1037.60299

MC‐AnaR Microcystin C52H80N10O12 1037.60354

S 40 [Asp3]MC‐YY Microcystin C54H67N7O14 1038.48243

[Gly1, Asp3, ADMAdda5, Dhb7]MC‐RR Microcystin C48H71N13O13 1038.53725

[d-Asp3 D-Glu(OCH3)6]MC-RR Microcystin C49H75N13O12 1038.57309

[d-Asp3 MSer7]MC-RR Microcystin C49H75N13O12 1038.57309

MC-RR Microcystin C49H75N13O12 1038.57309

[6(Z)- Adda5]MC-RR Microcystin C49H75N13O12 1038.57309

[d-Ser1- ADMAdda5]MC-LR Microcystin C50H74N10O14 1039.54587

[Met1, Asp3]MC‐LR Microcystin C50H76N10O12S 1041.54431

[ADMAdda5 MSer7]MC-LR Microcystin C50H76N10O14 1041.56152

[ADMAdda5, MeSer7]MC‐LR Microcystin C50H76N10O14 1041.56207

Glu(OCH3)6]MC-FR] Microcystin C53H73N10O12 1042.54877

[d-Asp3 MSer7]MC-RR Microcystin C48H75N13O13 1042.56801

[l-Ser7]MC- RR Microcystin C48H75N13O13 1042.56801 seco[d-Asp3]MC-RR Microcystin C48H75N13O13 1042.56801

[Asp3, Thr7]MC‐RR Microcystin C48H75N13O13 1042.56856

MC‐HphR Microcystin C53H74N10O12 1043.55659

MC‐M(O2)R (oxidation artefact) Microcystin C48H72N10O14S 1045.50284

MC-YR Microcystin C52H72N10O13 1045.53531

[D-Asp3, (E)-Dhb7]MC-HtyR Microcystin C52H72N10O13 1045.53531

[d-Asp3]MC-HtyR Microcystin C52H72N10O13 1045.53531

[Dha7]MC-HtyR Microcystin C52H72N10O13 1045.53531

[D-Asp3, (E)-Dhb7]MC-HtyR Microcystin C52H72N10O13 1045.53531

[D‐Asp3, (Z)‐Dhb7]MC‐HtyR Microcystin C52H72N10O13 1045.53586

MC‐RY Microcystin C52H72N10O13 1045.53586

Monochloro-hydroxy-MC-LR Microcystin C49H75ClN10O13 1047.52764

L‐Phe‐D‐MeAsp(β)‐L‐Arg‐Adda‐D‐ Microcystin C52H74N10O13 1047.55151 Glu(γ)‐Mdha‐D‐Ala‐OH

MC‐HphHph Microcystin C57H73N7O12 1048.53955

[D‐Asp3, L‐Ser7]MC‐HtyR Microcystin C51H72N10O14 1049.53077

[Asp3, MSer7]MC‐RY Microcystin C51H72N10O14 1049.53077

S 41 [Ser7]MC‐YR Microcystin C51H72N10O14 1049.53077

MC-(H4)YR Microcystin C52H76N10O13 1049.56661

[ADMAdda5]MC‐HilHar Microcystin C52H78N10O13 1051.58281

[Leu1, Asp3, ADMAdda5]MC‐LR Microcystin C52H78N10O13 1051.58281

[Leu1]MC‐HilR Microcystin C53H82N10O12 1051.61919

[Leu1]MC‐LHar Microcystin C53H82N10O12 1051.61919

[Leu1,Glu(OMe)6]MC‐LR Microcystin C53H82N10O12 1051.61919

[D‐Asp3, (E)‐Dhb7]MC‐HtyY Microcystin C55H69N7O14 1052.49808

MC‐YY Microcystin C55H69N7O14 1052.49808

[d-Asp3 ADMAdda5 Dhb7]MC-RR Microcystin C49H73N13O13 1052.55236

[Asp3 dmAdda5]MC-RR Microcystin C49H73N13O13 1052.55236

[Gly1, Asp3, ADMAdda5, Dhb7]MC‐ Microcystin C49H73N13O13 1052.55291 RHar

[d-Glu-OC2H3(CH3)OH6]MC-LR Microcystin C52H80N10O13 1053.59791

[Dha7]MC-WR Microcystin C53H71N11O12 1054.53564

[d-Asp3]MC-WR Microcystin C53H71N11O12 1054.53564

[DMAdda5]MC‐WR Microcystin C53H71N11O12 1054.53619

[Met1]MC‐LR Microcystin C51H78N10O12S 1055.55996

[Leu1, NMeSer7]MC‐LR Microcystin C52H82N10O13 1055.61411

[ADMAdda5]MC‐FR Microcystin C53H72N10O13 1057.53586

[D‐Glu(OMe)6]MC‐YR Microcystin C53H74N10O13 1059.55151

MC-HtyR Microcystin C53H74N10O13 1059.55200

[Asp3 MGlu6] MC-HtyR Microcystin C53H74N10O13 1059.55200

[Ser1, Asp3]MC‐HtyR Microcystin C52H72N10O14 1061.53077

[D‐Asp3]MC‐Y(OMe)R Microcystin C52H72N10O14 1061.53077

[DMAdda5]MC‐Y(OMe)R Microcystin C52H72N10O14 1061.53077

Monochloro-dihydroxy-MC-LR Microcystin C49H75ClN10O14 1063.52255

[l-Ser7]MC-HtyR Microcystin C52H74N10O14 1063.54587

[Asp3 MSer7]MC-HtyR Microcystin C52H74N10O14 1063.54587

[seco‐4/5][Asp3]MC‐HtyR Microcystin C52H74N10O14 1063.54642

S 42 [D‐Asp3, ADMAdda5]MC‐(H4)YR Microcystin C52H74N10O14 1063.54642

[MeSer7]MC‐RY Microcystin C52H74N10O14 1063.54642

[Asp3, MeSer7]MC‐YHar Microcystin C52H74N10O14 1063.54642

[MeSer7]MC‐YR Microcystin C52H74N10O14 1063.54642

[NMeSer7]MC‐YR Microcystin C52H74N10O14 1063.54642

MC‐HphHty Microcystin C57H73N7O13 1064.53446

[Leu1, ADMAdda5]MC‐LR Microcystin C53H79N10O13 1064.59063

[Leu1, Glu(OMe)6]MC‐HilR Microcystin C54H84N10O12 1065.63484

[D‐Asp3, (E)‐Dhb7]MC‐HtyHty Microcystin C56H71N7O14 1066.51373

[ADMAdda]MC-RR Microcystin C50H75N13O13 1066.56801

MC-HarHar Microcystin C51H79N13O12 1066.60439

[Leu1, Asp3]MC‐RR Microcystin C51H79N13O12 1066.60494

MC-WR Microcystin C54H73N11O12 1068.55129

[Leu1, Glu(OMe)6, NMeSer7]MC‐LR Microcystin C53H84N10O13 1069.62976

[M(O)1]MC‐LR Microcystin C51H78N10O13S 1071.55488

[Leu1, Asp3]MC‐HphR Microcystin C55H78N10O12 1071.58789

[Phe1]MC‐LR Microcystin C55H78N10O12 1071.58789

MC‐KynR (oxidised W) Microcystin C53H73N11O13 1072.54621

[d-Asp3 ADMAdda5]MC-HtyR Microcystin C53H72N10O14 1073.53022

[d-Asp3 ADMAdda5 Dhb7]MC-HtyR Microcystin C53H72N10O14 1073.53022

[ADMAdda5]MC‐YR Microcystin C53H72N10O14 1073.53077

MC‐MhtyR Microcystin C54H76N10O13 1073.56716

[Asp3, (E)‐Dhb7]MC‐HtyW Microcystin C57H70N8O13 1075.51406

MC‐RY(OMe) Microcystin C53H74N10O14 1075.54642

[Asp3]MC‐Hty(OMe)R Microcystin C53H74N10O14 1075.54642

MC‐Y(OMe)R Microcystin C53H74N10O14 1075.54642

[seco‐4/5]MC‐HtyR Microcystin C53H76N10O14 1077.56207

[ADMAdda5]MC‐(H4)YR Microcystin C53H76N10O14 1077.56207

[MSer7]MC‐HtyR Microcystin C53H76N10O14 1077.56207

[Leu1, ADMAdda5]MC‐LHar Microcystin C54H82N10O13 1079.61411

S 43 [ADMAdda5]MC‐RHar Microcystin C51H77N13O13 1080.58421

[Leu1]MC‐RR Microcystin C52H81N13O12 1080.62059

MC‐OiaR (oxidised W) Microcystin C54H73N11O13 1084.54621

[M(O)1, Glu(OMe)6]MC‐LR Microcystin C52H80N10O13S 1085.57053

[Leu1]MC‐HphR Microcystin C56H80N10O12 1085.60354

[ADMAdda5]MC‐(H4)YHar Microcystin C54H78N10O14 1091.57772

Dichloro-dihydroxy-MC-LR Microcystin C49H74N10O14Cl2 1097.48358

MC‐NfkR (oxidised W) Microcystin C54H73N11O14 1100.54113

[Leu1]MC‐HtyrR Microcystin C56H80N10O13 1101.59846

Trichloro-hydroxy-MC-LR Microcystin C49H73N10O13Cl3 1115.44969

[l-MLan7]MC-LR Microcystin C52H81N11O14S 1116.57579

MC-LR-cysteine Microcystin C52H81N11O14S 1116.57580

[L‐MeLan7]MC‐LR Microcystin C52H81N11O14S 1116.57634

MC-RR-Cys Microcystin C52H82N14O14S 1159.59284

MC-YR-Cys Microcystin C55H79N11O15S 1166.55506

MC-LR-gamma-glutamylcystein Microcystin C57H88N12O17S 1245.61839

MC-LR glutathione Microcystin C59H91N13O18S 1302.63986

MC-RR-GSH Microcystin C59H92N16O18S 1345.65690

MC-YR-GSH Microcystin C62H89N13O19S 1352.61912

Microginin 511 Microginin C25H41N3O6S 512.27888

Microginin 527 Microginin C25H41N3O7S 528.27380

Microginin 527 methyl ester Microginin C26H43N3O7S 542.28945

Microginin 91A Microginin C28H52N4O6Cl 576.36481

Nostoginin BN578 Microginin C30H51N4O7 580.38305

Oscillaginin B Microginin C29H48N4O8 581.35449

Microginin AL584 Microginin C28H45ClN4O7 585.30495

Microginin KR604 Microginin C32H52N4O7 605.39088

Microginin 91B Microginin C28H51N4O6Cl2 610.32584

Microginin 612 Microginin C32H44N4O8 613.32319

Oscillaginin A Microginin C29H47ClN4O8 615.31552

S 44 Microginin KR638 Microginin C32H51ClN4O7 639.35190

Microginin 646 Microginin C32H43Cl1N4O8 647.28422

Oscillaginin C Microginin C29H46Cl2N4O8 649.27655

Microginin 674 Microginin C34H50N4O8S 675.34221

Microginin 680 Microginin C32H42Cl2N4O8 681.24525

Microginin 688 Microginin C35H52N4O8S 689.35786

Microginin 690 Microginin C34H50N4O9S 691.33713

Microginin T2 Microginin C36H51N5O9 698.37595

Microginin 704 Microginin C35H52N4O9S 705.35278

Microginin 91C Microginin C37H62N5O8 705.46712

Microginin 713 Microginin C37H55N5O9 714.40725

Microginin FR5 Microginin C38H55N5O9 726.40725

Microginin FR3 Microginin C37H53N5O10 728.38652

Microginin FR1 Microginin C38H57N5O9 728.42340

Cyanostatin A Microginin C38H57N5O9 728.42340

Microginin T1 Microginin C36H50ClN5O9 732.33698

Microginin 91D Microginin C37H60N5O8Cl 738.42032

Microginin 91D Microginin C37H61N5O8Cl 739.42814

Microginin FR6 Microginin C39H57N5O9 740.42290

Microginin FR4 Microginin C38H55N5O10 742.40217

Microginin FR2 Microginin C39H59N5O9 742.43856

Nostoginin BN741 Microginin C39H59N5O9 742.43856

Microginin FR7 Microginin C38H57N5O10 744.41832

Microginin FR10 Microginin C40H56N6O8 749.42324

Microginin FR9 Microginin C39H54N6O9 751.40250

Cyanostatin B Microginin C40H59N5O9 754.43855

Microginin SD755 Microginin C40H61N5O9 756.45420

Microginin 299D Microginin C36H56Cl2N5O8 757.35787

Microginin 757 Microginin C39H59N5O10 758.43347

Microginin 764 Microginin C40H56N6O9 765.41815

Microginin 767 Microginin C41H61N5O9 768.45420

S 45 Microginin 767B Microginin C41H61N5O9 768.45420

Microginin FR8 Microginin C41H61N5O9 768.45421

Microginin KR767 Microginin C41H61N5O9 768.45421

Microginin 478 Microginin C41H63N5O9 770.46985

Microginin FR13 Microginin C41H63N5O9 770.47035

Microginin 99A Microginin C40H58ClN5O8 772.40467

Microginin 91E Microginin C37H60N5O8Cl2 773.38917

Microginin KR815 Microginin C42H62N5O9 781.46203

Microginin KR781 Microginin C42H63N5O9 782.46986

Microginin FR12 Microginin C42H65N5O9 784.48551

Microginin KR787 Microginin C40H58ClN5O9 788.39958

Microginin KR801 Microginin C41H60ClN5O9 802.41523

Microginin 99B Microginin C40H57Cl2N5O8 806.36570

Microginin KR835 Microginin C41H59Cl2N5O9 836.37626

Microginin 299C Microginin C45H68N6O10 853.50697

Microginin 299A Microginin C45H67ClN6O10 887.46800

Microginin 51A Microginin C49H68N6O11 917.50188

Microginin 299B Microginin C45H66Cl2N6O10 921.42902

Microginin 51B Microginin C50H70N6O11 931.51753

Microphycin AL828 Microphycin C40H60O11N8 829.44543

Microphycin KB921 Microphycin C49H63N9O9 922.48215

[l‐Val2]NOD Nodularin C40H57N5O10 768.41782

[DMAdda3]nodularin Nodularin C40H58N8O10 811.43487

[(6Z)-Adda3]nodularin Nodularin C40H58N8O10 811.43487

[d‐Asp1]NOD Nodularin C40H58N8O10 811.43540

[DMAdda3]NOD Nodularin C40H58N8O10 811.43540

[dhb5]NOD Nodularin C40H58N8O10 811.43540

[DAsp1]nodularin Nodularin C40H60N8O10 813.45052

Nodularin Nodularin C41H60N8O10 825.45052

NOD‐R Nodularin C41H60N8O10 825.45110

S 46 [6(Z)‐Adda3]NOD Nodularin C41H60N8O10 825.45110

Dihydronodularin Nodularin C41H62N8O10 827.46617

[l‐Har2]NOD Nodularin C42H62N8O10 839.46617

[Glu4(OMe)]NOD Nodularin C42H62N8O10 839.46670

[MeAdda3]NOD Nodularin C42H62N8O10 839.46670

Adda‐d‐Glu(γ)‐Mdhb‐d‐MeAsp(β)‐l-Arg‐ Nodularin C42H62N8O11 843.46160 OH

Nodularin-R-phenylglyoxal (IIc) Nodularin C48H60N8O10 909.45052

Nodularin-R-phenylglyoxal (IIb) Nodularin C48H62N8O11 927.46108

Nodularin-R-phenylglyoxal (IIa) Nodularin C48H62N8O11 927.46108

Apramide D other C17H22NOCl5 432.02168

Microguanidine LA772 other C29H48N4O14S3 773.24019

Apramide G other C44H73N7O6S 828.54158

Apramide B other C51H78N8O8S 963.57361

Apramide A other C52H80N8O8S 977.58926

Apramide C other C52H82N8O8S 979.60491

Apramide E other C53H80N8O8S 989.58926

Apramide F other C54H84N8O8S 1005.62056

Spumigin C Spumigin C30H40N6O8 613.29804

Spumigin J Spumigin C32H44N4O8 613.32319

Spumigin A Spumigin C31H44N6O7 613.33497

Spumigin B1 Spumigin C31H42N6O8 627.31369

Spumigin B2 Spumigin C31H42N6O8 627.31369

S 47 References

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S 49