Ligand cytidine 5'-monophosphate

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Basic Ligand Information

Molecular Structure

C₉H₁₄N₃O₈P

cytidine 5'-monophosphate

IERHLVCPSMICTF-XVFCMESISA-N

Synonyms:

5'-CMP, 5'-cytidylic acid, 5'CMP, CMP, cytidine-5'-monophosphate, cytidine-5'-phosphate, cytidine 5'-phosphate, cytidine monophosphate, cytidine phosphate, cytidyl 5'-monophosphate, cytidylate, cytidylic acid, D-CMP

BRENDA

cardiolipin biosynthesis, coenzyme A metabolism, isoprenoid biosynthesis, lipid A biosynthesis, lipid metabolism

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KEGG

Nucleotide metabolism, Pyrimidine metabolism

MetaCyc

3-phosphoinositide biosynthesis, ABH and Lewis epitopes biosynthesis from type 1 precursor disaccharide, ABH and Lewis epitopes biosynthesis from type 2 precursor disaccharide, alpha-dystroglycan glycosylation, anandamide biosynthesis I

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Show all BRENDA pathways known for cytidine 5'-monophosphate

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (17 results)

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CMP + phosphatidylcholine = ?

CMP + diphosphate + N-[(R)-4'-phosphopantothenoyl]-L-cysteine = CTP + (R)-4'-phosphopantothenate + L-cysteine

648960

1u80, 3D-view

In Vivo Product in Enzyme-catalyzed Reactions (125 results)

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2.3.1.45

acetyl-CoA + CMP-N-acetylneuraminate = CoA + N-acetyl-9-O-acetylneuraminate + CMP

2.4.3.1

8 entries

2.4.3.10

CMP-N-acetyl-beta-neuraminate + N-acetyl-alpha-neuraminyl-(2->3)-beta-D-galactosyl-(1->3)-N-acetyl-beta-D-glucosaminyl-R = CMP + N-acetyl-alpha-neuraminyl-(2->3)-beta-D-galactosyl-(1->3)-[N-acetyl-alpha-neuraminyl-(2->6)]-N-acetyl-beta-D-glucosaminyl-R

3-deoxy-alpha-D-manno-oct-2-ulopyranosyl-(2->6)-2-deoxy-2-[[(3R)-3-hydroxypentadecanoyl]amino]-3-O-[(3R)-3-hydroxytetradecanoyl]-4-O-phosphono-beta-D-glucopyranosyl-(1->6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[[(3R)-3-hydroxytetradecanoyl]amino]-1-O-phosphono-alpha-D-glucopyranose + CMP-3-deoxy-D-manno-octulosonate = 3-deoxy-alpha-D-manno-oct-2-ulopyranosyl-(2->4)-3-deoxy-alpha-D-manno-oct-2-ulopyranosyl-(2->6)-2-deoxy-2-[[(3R)-3-hydroxypentadecanoyl]amino]-3-O-[(3R)-3-hydroxytetradecanoyl]-4-O-phosphono-beta-D-glucopyranosyl-(1->6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[[(3R)-3-hydroxytetradecanoyl]amino]-1-O-phosphono-alpha-D-glucopyranose + CMP

2.4.99.14

3-deoxy-alpha-D-manno-oct-2-ulopyranosyl-(2->4)-3-deoxy-alpha-D-manno-oct-2-ulopyranosyl-(2->6)-2-deoxy-2-[[(3R)-3-hydroxypentadecanoyl]amino]-3-O-[(3R)-3-hydroxytetradecanoyl]-4-O-phosphono-beta-D-glucopyranosyl-(1->6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[[(3R)-3-hydroxytetradecanoyl]amino]-1-O-phosphono-alpha-D-glucopyranose + CMP-3-deoxy-D-manno-octulosonate = 3-deoxy-alpha-D-manno-oct-2-ulopyranosyl-(2->8)-3-deoxy-alpha-D-manno-oct-2-ulopyranosyl-(2->4)-3-deoxy-alpha-D-manno-oct-2-ulopyranosyl-(2->6)-2-deoxy-2-[[(3R)-3-hydroxypentadecanoyl]amino]-3-O-[(3R)-3-hydroxytetradecanoyl]-4-O-phosphono-beta-D-glucopyranosyl-(1->6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[[(3R)-3-hydroxytetradecanoyl]amino]-1-O-phosphono-alpha-D-glucopyranose + CMP

2.4.99.15

3-deoxy-alpha-D-manno-oct-2-ulopyranosyl-(2->8)-3-deoxy-alpha-D-manno-oct-2-ulopyranosyl-(2->4)-3-deoxy-alpha-D-manno-oct-2-ulopyranosyl-(2->6)-2-deoxy-2-[[(3R)-3-hydroxytetradecanoyl]amino]-3-O-[(3R)-3-hydroxytetradecanoyl]-4-O-phosphono-beta-D-glucopyranosyl-(1->6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[[(3R)-3-hydroxytetradecanoyl]amino]-1-O-phosphono-alpha-D-glucopyranose + CMP-3-deoxy-D-manno-octulosonate = 3-deoxy-alpha-D-manno-oct-2-ulopyranosyl-(2->8)-[3-deoxy-alpha-D-manno-oct-2-ulopyranosyl-(2->4)]-3-deoxy-alpha-D-manno-oct-2-ulopyranosyl-(2->4)-3-deoxy-alpha-D-manno-oct-2-ulopyranosyl-(2->6)-2-deoxy-2-[[(3R)-3-hydroxytetradecanoyl]amino]-3-O-[(3R)-3-hydroxytetradecanoyl]-4-O-phosphono-beta-D-glucopyranosyl-(1->6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[[(3R)-3-hydroxytetradecanoyl]amino]-1-O-phosphono-alpha-D-glucopyranose + CMP

2.7.1.213

cytidine + ATP = CMP + ADP

CDP-choline + sphingosine = CMP + sphingosylphosphorylcholine

CDP-glycerol + (glycerophosphate)n = CMP + (glycerophosphate)n+1

2.7.8.14

CDPribitol + (ribitol phosphate)n = CMP + (ribitol phosphate)n+1

645344, 0

2.7.8.2

5 entries

2.7.8.22

CDP-choline + 1-alkenyl-2-acylglycerol = CMP + plasmenylcholine

643767

2.7.8.24

CDP-diacylglycerol + choline = CMP + phosphatidylcholine

0, 394955, 394956

2.7.8.3

cytidine diphosphate choline + N-acyl-threo-trans-sphingosine = CMP + sphingomyelin

2.7.8.34

CDP-1L-myo-inositol + 1L-myo-inositol 1-phosphate = CMP + bis(1L-myo-inositol) 3,1'-phosphate 1-phosphate

2.7.8.38

2 entries

2.7.8.39

CDP-2,3-bis-O-(phytanyl)-sn-glycerol + 1L-myo-inositol 1-phosphate = CMP + 1-archaetidyl-1D-myo-inositol 3-phosphate

2.7.8.4

CDP-ethanolamine + L-serine = CMP + L-serine-ethanolamine phosphate

CDP-ribitol + 4-O-[(2R)-1-glycerophospho]-N-acetyl-beta-D-mannosaminyl-(1->4)-N-acetyl-alpha-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol = CMP + 4-O-[1-D-ribitylphospho-(2R)-1-glycerophospho]-N-acetyl-beta-D-mannosaminyl-(1->4)-N-acetyl-alpha-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol

CDP-diacylglycerol + 1L-myo-inositol 1-phosphate = CMP + 1-phosphatidyl-1D-myo-inositol 3-phosphate

3.6.1.13

CDP-choline + H2O = CMP + phosphocholine

3.6.1.15

CDP + H2O = CMP + phosphate

3.6.1.16

CDPglycerol + H2O = CMP + L-alpha-glycerophosphate

209892

3.6.1.26

CDPdiacylglycerol + H2O = CMP + phosphatidate

CDP-choline + H2O = CMP + phosphocholine

3.6.1.6

CDP + H2O = CMP + phosphate

3.6.1.8

CTP + H2O = CMP + diphosphate

CTP + (R)-4'-phosphopantothenate + L-cysteine = CMP + diphosphate + N-[(R)-4'-phosphopantothenoyl]-L-cysteine

1u80, 3D-view

6.3.2.51

CTP + (R)-4'-phosphopantothenate + L-cysteine = CMP + diphosphate + N-[(R)-4'-phosphopantothenoyl]-L-cysteine

Substrate in Enzyme-catalyzed Reactions (147 results)

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1.17.4.2

CMP + reduced thioredoxin = dCMP + oxidized thioredoxin + H2O

5,10-methylenetetrahydrofolate + CMP = dihydrofolate + 5-methylcytidylate

sucrose + CMP = D-fructose + CMP 1-glucoside

685765

2.4.2.57

CMP + phosphate = cytosine + alpha-D-ribose 1,5-bisphosphate

725279, 726487

2.4.3.4

CMP + 3-O-[alpha-Neu5Ac-(2->3)-beta-D-Gal-(1->3)-alpha-D-GalNAc]-L-tyrosyl-[protein] = CMP-N-acetyl-beta-neuraminate + 3-O-[beta-D-Gal-(1->3)-alpha-D-GalNAc]-L-tyrosyl-[protein]

744308

2.4.3.8

CMP + trisialoganglioside GT1a = CMP-N-acetylneuraminate + disialoganglioside GD1a

CMP + trans-farnesyl diphosphate = GDP + trans-farnesyl triphosphate

CMP + [phosphate]n = CDP + [phosphate]n-1

722511, 722513

2.7.7.19

ATP + CMP = diphosphate + ?

1-stearoyl-2-arachidonoylphosphatidylinositol + CMP = CDP-1-stearoyl-2-arachidonoylglycerol + myo-inositol

CMP + 1-(3-sn-phosphatidyl)-sn-glycerol 3-phosphate = CDP-diacylglycerol + sn-glycerol 3-phosphate

5'-CMP + H2O = cytidine + phosphate

CMP + H2O = cytosine + phosphate

749824

3.2.2.10

5'-CMP + H2O = cytosine + ribose 5-phosphate

137031

3.5.4.12

CMP + H2O = UMP + NH3

289009, 289004, 288999, 289003, 289005, 288998, 289018

3.5.4.5

CMP + H2O = ?

650635

3.6.1.2

cytidine-5'-monophosphate + H2O = ?

209931

6.3.2.5

CMP + diphosphate + N-[(R)-4'-phosphopantothenoyl]-L-cysteine = CTP + (R)-4'-phosphopantothenate + L-cysteine

648960

1u80, 3D-view

Product in Enzyme-catalyzed Reactions (646 results)

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2.1.1.45

5,10-methylenetetrahydrofolate + 2'-deoxycytidine 5'-monophosphate = dihydrofolate + cytidine phosphate

2.3.1.45

acetyl-CoA + CMP-N-acetylneuraminate = CoA + N-acetyl-9-O-acetylneuraminate + CMP

AMP + cytidine = adenosine + cytidine 5'-phosphate

CDP + D-glucose = CMP + D-glucose 6-phosphate

2.7.1.173

ATP + cytidine = ADP + CMP

CDP + CDP = CTP + CMP

642556, 0

2.7.6.1

CTP + D-ribose 5-phosphate = CMP + 5-phospho-alpha-D-ribose 1-diphosphate

642716, 642729, 0, 642738, 642711

2.7.6.2

CTP + thiamine = CMP + thiamine diphosphate

2.7.7.103

2 entries

2.7.7.74

CDP-glycerol + 1L-myo-inositol 1-phosphate = CMP + 1-(1X-glyceryl) myo-inosityl phosphate 3-phosphate

2.7.8.1

26 entries

2.7.8.10

CDP-choline + sphingosine = CMP + sphingosylphosphorylcholine

CDP-choline + 1-alkenyl-2-acylglycerol = CMP + plasmenylcholine

643767

2.7.8.24

CDP-diacylglycerol + choline = CMP + phosphatidylcholine

0, 394955, 394956

CDP-ethanolamine + L-serine = CMP + L-serine-ethanolamine phosphate

UDP-D-galactose + phosphoryl-polyprenol = galactosyl-diphospho-polyprenol + CMP

single-stranded oligodeoxycytidylate + H2O = single-stranded oligodeoxycytidylate + cytidyl 5'-monophosphate

CDP + H2O = CMP + phosphate

3.1.3.7

cytidine 3',5'-bisphosphate + H2O = cytidine 5'-phosphate + phosphate

3.1.3.9

glucose + CDP = glucose 6-phosphate + CMP

3.1.30.1

polycytosylic acid + H2O = 5'-CMP + 5'-phosphooligonucleotides

134961, 134971, 134998

CDP + H2O = CMP + phosphate

3.1.4.17

3',5'-cCMP + H2O = 5'-CMP

3.1.4.37

CDP + H2O = CMP + phosphate

3.1.4.40

CMP-N-acylneuraminate + H2O = CMP + N-acylneuraminate

0, 135472, 135473, 135468

3.6.1.12

CTP + H2O = CMP + diphosphate

3.6.1.13

6 entries

3.6.1.15

CDP + H2O = CMP + phosphate

3.6.1.16

2 entries

3.6.1.24

cytidine 5'-p-nitrophenylphosphate + H2O = p-nitrophenol + CMP

7-methylguanosine(5')triphospho(5')cytosine + H2O = 7-methylguanosine(5')monophosphate + CDP + CMP + 7-methylguanosine(5')diphosphate

3.6.1.41

adenosine 5'-P(1)-triphosphate-P(3)-5''-cytidine + H2O = ADP + CMP + CDP + AMP

CTP + H2O = CMP + diphosphate

3.6.1.6

2 entries

3.6.1.65

CTP + H2O = CMP + diphosphate

3.6.1.8

CTP + H2O = CMP + diphosphate

CDP-2,3-di-O-phytanyl-sn-glycerol + 1D-myo-inositol 1-phosphate = archaetidylinositol phosphate + CMP

6.2.1.1

CTP + acetate + CoA = CMP + diphosphate + acetyl-CoA

6.2.1.12

CTP + ferulate + CoA = CMP + diphosphate + feruloyl-CoA

6.2.1.2

CTP + butyrate + CoA = CMP + diphosphate + butyryl-CoA

6.2.1.22

CTP + acetate + citrate (pro-3S)-lyase = CMP + diphosphate + citrate(pro-3S)-lyase

6.2.1.24

CTP + phytanate + CoA = CMP + diphosphate + phytanoyl-CoA

6.2.1.26

CTP + o-succinylbenzoate + CoA = CMP + diphosphate + o-succinylbenzoyl-CoA

6.2.1.27

CTP + 4-hydroxybenzoate + CoA = CMP + 4-hydroxybenzoyl-CoA + diphosphate

6.2.1.30

CTP + phenylacetate + CoA = CMP + diphosphate + phenylacetyl-CoA

6.2.1.36

3-hydroxypropanoate + CTP + coenzyme A = 3-hydroxypropanoyl-CoA + CMP + diphosphate

6.2.1.8

CTP + oxalate + CoA = CMP + diphosphate + oxalyl-CoA

6.3.2.1

CTP + (R)-pantoate + beta-alanine = CMP + diphosphate + (R)-pantothenate

6.3.2.11

CTP + L-His + beta-Ala = CMP + phosphate + carnosine

997

6.3.2.5

CTP + (R)-4'-phosphopantothenate + L-cysteine = CMP + diphosphate + N-[(R)-4'-phosphopantothenoyl]-L-cysteine

1u80, 3D-view

6.3.2.51

CTP + (R)-4'-phosphopantothenate + L-cysteine = CMP + diphosphate + N-[(R)-4'-phosphopantothenoyl]-L-cysteine

6.3.4.10

2 entries

6.3.4.9

CTP + biotin + apo-[methylmalonyl-CoA:pyruvate carboxyltransferase] = CMP + diphosphate + [methylmalonyl-CoA:pyruvate carboxyltransferase]

6.3.5.4

CTP + L-Asp + L-Gln = CMP + diphosphate + Asn + Glu

6.5.1.4

CTP + RNA 3'-terminal-phosphate = CMP + diphosphate + RNA terminal-2',3'-cyclic-phosphate

6.5.1.8

2 entries

Enzyme Cofactor/Cosubstrate (3 results)

activates

Activator in Enzyme-catalyzed Reactions (11 results)

slight activation

2',3'-cyclic nucleotide phosphodiesterase activity

1 mM, 25% activation

cytidine 5'-monophosphate is not required by the trans-sialidase activity of the enzyme but enhances the trans-sialidase activity modestly as a non-essential activator

703911

3.2.1.24

25% activation at 1 mM