SUPPORTING INFORMATION

Mooreamide: A Cannabinomimetic Lipid from the Marine Cyanobacterium

Moorea bouillonii

Emily Mevers, Teatulohi Matainaho, Marco Allara’, Vincenzo Di Marzo and William H.

Gerwick

NMR Spectroscopic Data and Biological Data for Mooreamide (1)

1 Figure S1 H NMR (500 MHz, CDCl3) spectrum of mooreamide (1)

13 Figure S2 C NMR (125 MHz, CDCl3) spectrum of mooreamide (1)

1 Figure S3 HSQC ( H 500 MHz, CDCl3) spectrum of mooreamide (1)

1 Figure S4 HMBC ( H 600 MHz, CDCl3) spectrum of mooreamide (1)

1 Figure S5 COSY ( H 500 MHz, CDCl3) spectrum of mooreamide (1)

1 Figure S6 NOESY ( H 600 MHz, CDCl3) spectrum of mooreamide (1) Figure S7 Displacement of [3H]-CP 55,940 by mooreamide (1) 1 Figure S1: H NMR (500 MHz, CDCl3) spectrum of mooreamide (1)

1782H-2_3-A-5-G STANDARD PROTON PARAMETERS 1100

1000

900

800

700

600

500

400

300

200

100

0

-100

7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 f1 (ppm) 13 Figure S2: C NMR (125 MHz, CDCl3) spectrum of mooreamide (1) 9 5 5 0 0 2 6 0 1 6 6 1 9 1 0 5 9 1 6 8 9 1 4 4 4 3 8 2 7 6 0 3 8 4

1782H-2_3-A-5-G_CDCl3_vx500MHz 1 ...... 13 9 1 8 7 8 0 0 4 8 7 5 5 0 7 5 9 6 2 0 9 6 4 1 4 ...... 6 4 3 3 3 3 2 2 2 2 1 3 2 9 3 2 2 1 9 8 8 8 6 Std carbon 0 1 1 1 1 1 1 1 1 1 1 1 6 5 3 3 3 3 3 2 2 2 2 1 -

12

11

10

9

8

7

6

5

4

3

2

1

0

-1

170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 -10 f1 (ppm) 1 Figure S3: HSQC ( H 500 MHz, CDCl3) spectrum of mooreamide (1)

1782H-2_3-A-5-G_gHSQC STANDARD PROTON PARAMETERS 10

20

30

40

50

60

70 ) m p p ( 80 1 f

90

100

110

120

130

140

150 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 f2 (ppm) 1 Figure S4: HMBC ( H 600 MHz, CDCl3) spectrum of mooreamide (1)

1782H2/2 HMBC (hmbcgplpndqf) 10 Cryoprobe 062708 20

30

40

50

60

70

80 ) m p p (

90 1 f 100

110

120

130

140

150

160

170

6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 f2 (ppm) 1 Figure S5: COSY ( H 500 MHz, CDCl3) spectrum of mooreamide (1)

1782H-23-A-56-gCOSY STANDARD PROTON PARAMETERS 0.5

1.0

1.5

2.0

2.5

3.0 ) m p

3.5 p (

1 f 4.0

4.5

5.0

5.5

6.0

6.5

6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 f2 (ppm) 1 Figure S6: NOESY ( H 600 MHz, CDCl3) spectrum of mooreamide (1)

1782H2/5 0.5 NOESY (noesyph) Cryoprobe 062708 1.0

1.5

2.0

2.5

3.0

3.5

4.0

4.5

5.0

5.5

6.0

6.5

6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 f2 (ppm) Figure S7: Displacement of [3H]-CP 55,940 by mooreamide (1).

g 100 n f i o d t n i n

b 75 e

0 m 4 e 9 c , a 5 50 l 5 p s P i d C

- 25 ] % H 3 [ 0 -10 -8 -6 -4 log[M]