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) + (acetylating) (NADP reductase (NADPH) 3 (glutamine-hydrolysing) P 1.2.1.18 Malonate semialdehyde 1.3.1.2 Dihydropyrimidine dehydrogenase 1.3.1.14 Orotate reductase (NADH) 1.6.4.51.17.4.1 -diphosphate Thioredoxin reductase (NADPH) 2.1.1.45 2.1.3.22.3.2.23 phosphorylase Aspartate carbamoyltransferase 2.4.2.- Pentosyltransferase 2.4.2.2 - phosphorylase 2.4.2.3 (pyrimidine) phosphorylase 2.4.2.42.4.2.9 phosphoribosyltransferase phosphorylase 2.4.2.10 Orotate phosphoribosyltransferase 2.4.2.23 Deoxyuridine phosphorylase 2.6.1.18 3-Alanine-pyruvate transaminase 2.6.1.22 3-Amino-2-methylpropionate transaminase 2.7.1.21 Thymidine 2.7.1.48 Uridine kinase 2.7.1.74 kinase 2.7.4.4 Nucleoside-phosphate kinase 2.7.4.6 Nucleoside-diphosphate kinase 3.1.3.31 Nucleotidase 3.5.1.6 3-Ureidopropionase 3.5.2.2 3.5.2.3 3.5.4.1 deaminase 3.5.4.5 deaminase deaminase 3.5.4.12 dCMP 3.5.4.14 3.6.1.6 Nucleoside-diphosphatase 3.6.1.15 Nucleoside-triphosphatase 4.1.1.23 Orotidine-5-phosphate decarboxylase synthase 6.3.4.2 CTP 6.3.5.5 Carbamoylphosphate synthase

CCH CH

CH

O O

= = O O C C O H N N H OH P O UMP P 2 HN OH H -O- O=C H P Uridine -5- -O-CH 3 + P 3 -O- 3 P CCH

CH

+ CCH CH CCH

CH CH 2 = 3 = Deoxyribose- C N O O Deoxyribose C N C N H O CO NADPH+H NADP CCH CH HN O=C 4.1.2.3 HN HN HN O=C O=C C O Deoxyribose- N ADP ADP ATP ADP ATP ATP - 2.7.1.48 2.7.4.6 3 1.3.1.2 2.7.4.4 HN P O=C triphosphate diphosphate

CCH CH

C.COO

O O

= = i dTTP dTDP dTMP P O O P C O H N N O i O i 2.4.2.4 O Thymidine i 2 3.6.1.6 2 H OH 2 P P P 3.1.3.31 H O H Thymidine-P 3.6.1.15 P-O-P H 2 HN OH H O=C H Orotidine- Thymidine Bifunctional 3 -O-CH Thymidine i P -1- - 1.3.1.2 3 CCH CH PP Dihydrofolate 2.1.1.45 CH CH 2 O C N 2 N Deoxyribose- 2 2.7.7.7 THF CHCH O C N CH Deoxyribose CH CH Methylene- - 4 - HN 2.4.2.10 H PRPP O=C N H 510 ADP N C C N O N H C O P P HN ATP N O=C .COO H

C C 2.7.1.48 = HN HN n O=C Dihydrothymine C O N H O=C n+1 CH CH C N Orotate DNA DNA H N N Deoxyribose- O C O i dUMP O= DNA 2 P A 3.1.3.31 H I 2 N Deoxyuridine

R A I 2

D dTMP R O=C + HO

Deoxyuridine- D + N UQH 4 4

N

O

O H

H NH CH CH NH

2 3 C

1.3.1.14 C O O

NH

C 2 T 2 2

T H N

I I 3.5.4.12 2.7.7.7 UQ

O M - - 3.5.4.14

M H H O CHCH 2 CH CH CH N 2 - H 2 H O=C H OH COO COO H H C C N N CH H - 2 P HCOO H -O i C C ADP P

2 2 -O-

2.7.1.74 P ATP O=C O=C ADP = P ADP HN O HN ATP 3-Ureidoisobutyrate ATP -- N H 3-Ureidopropionate C O P P 2.7.4.6 2.7.4.4 P-O- P C N 2.4.2.3 Dihydroorotate H dCMP O= dCDP 2 3.5.1.6 O P 2 3.5.1.6 O O i i O i diphosphate 3.6.1.6 2 2 H 2 Deoxycytidine CH CH 3.1.3.31 P P P dCTP CO 3.6.1.15 2 Deoxycytidine H H H 3 3.5.2.3 NH C Deoxyribose- N Deoxycytidine- + Deoxyribose-1- CH CH 2 NH - CH Deoxycytidine triphosphate CH N 2 3

N Ribose

C NH

O=C n

i 2 NH i 2 2 2 C

Deoxyribose- N (S-S) x N H HCOO -

-

- o C CH C CH CH PP

N CHCH d PRPP N O=C NADPH+H OO H

e P -

r O=C N 2.4.2.9 C 1.6.4.5 COO N C 1.17.4.1 O

o COO + 2 2 + i ALVAGE HN N P h S HN C -- T 2 3--Alanine O H O= NADP (2SH) P- - CH CH 2 3-Aminoisobutyrate CH Enzyme CH 2 Carbamoylaspartate NH PYRIMIDINE C H N ADP ADP PRPP NH C N Ribose Pyruvate ATP i ADP N ADP P ATP ATP P 2.7.1.74 N - 2.7.4.6 O=C 2.7.4.4 2.6.1.18 ATP 2.6.1.22 O=C 2 2.1.3.2 diphosphate H HCOO - i CTP Cytosine i Cytidine C C Alanine P P O i 2.4.2.3 O Cytidine- i O 2 i OO - 3.6.1.6 P 2 2 P - P 3.6.1.15 H C N H 3.1.3.31 2 H Aspartate P CDP H CMP P CH Cytidine CH 2 2 3 CH CH 2.7.7.6 2 CH CH I 2 - Ribose C N NH Ribose-1- CH + NH C N C NH N H Ribose- C N 4 2 P-O O= H H OH Malonate N OHCCH COO HN OHCCHCOO NH O=C Glutamate semialdehyde n HN 2 n+1 H O=C Trifunctional i OH O=C P 3.5.4.1 H i 3.5.4.5 Methylmalonate O Carbamoyl- RNA 2 RNA RNA -O PP 6.3.4.2 H NAD(P) PRPP P HSCoA O-CH 2 2.4.2.9 AGE -- ALV ATP

S P P Glutamate - 1.2.1.18 CO i P COO NAD(P)H 2 - Glutamine i ADP ADP ATP ATP 2.7.7.6 ADP P ATP P CH 2.7.4.4 Ribose-1- 2 2.7.4.6 2ADP 2.7.1.48 2.4.2.3 3 6.3.5.5 P diphosphate CH COO Uracil 2ATP - CH CH -O- Uridine Acetyl-CoA O i P 3.6.1.6 OOCCH O i Succinyl-CoA 2 O i P 2 O PP 3.6.1.15 P 2 C O H N H P 2 UDP 3.1.3.31 H -P UTP H - UMP P H e Uridine- - CH CH CH CH CH CH HN 3 CH O=C CH N Ribose- - O- Uridine Ribose O N O C C O C N N Ribos Ribose- -O- N O C HCO HN HN HN O=C O=C O=C HN Glutamine O=C

semialdehyde

BIOSYNTHESIS DEGRADATION

PYRIMIDINE

PYRIMIDINE

DIPHOSPHATES BASES MONOPHOSPHATES TRIPHOSPHATES

PYRIMIDINE

NUCLEOSIDE NUCLEOSIDE NUCLEOSIDE