Ligand cytidine 5'-monophosphate

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Basic Ligand Information

Molecular Structure

C₉H₁₄N₃O₈P

cytidine 5'-monophosphate

IERHLVCPSMICTF-XVFCMESISA-N

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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

Related pathways

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, anandamide biosynthesis II, archaetidylinositol biosynthesis, archaetidylserine and archaetidylethanolamine biosynthesis, arginomycin biosynthesis, bacimethrin and bacimethrin pyrophosphate biosynthesis, biosynthesis of Lewis epitopes (H. pylori), blasticidin S biosynthesis, C25,25 CDP-archaeol biosynthesis, cardiolipin and phosphatidylethanolamine biosynthesis (Xanthomonas), cardiolipin biosynthesis I, cardiolipin biosynthesis II, cardiolipin biosynthesis III, cell-surface glycoconjugate-linked phosphocholine biosynthesis, cell-surface glycoconjugate-linked phosphonate biosynthesis, ceramide phosphoethanolamine biosynthesis, choline biosynthesis III, CMP phosphorylation, coenzyme A biosynthesis I (bacteria), coenzyme A biosynthesis III (archaea), complex N-linked glycan biosynthesis (vertebrates), D-myo-inositol (1,4,5)-trisphosphate biosynthesis, di-myo-inositol phosphate biosynthesis, diacylglycerol biosynthesis (PUFA enrichment in oilseed), Escherichia coli serotype O:104 O antigen biosynthesis, Escherichia coli serotype O:56 O antigen biosynthesis, fosfomycin biosynthesis, FR-900098 and FR-33289 antibiotics biosynthesis, gala-series glycosphingolipids biosynthesis, ganglio-series glycosphingolipids biosynthesis, globo-series glycosphingolipids biosynthesis, Kdo transfer to lipid IVA (Brucella), Kdo transfer to lipid IVA (Chlamydia), Kdo transfer to lipid IVA (E. coli), Kdo transfer to lipid IVA (generic), Kdo transfer to lipid IVA (H. pylori), Kdo transfer to lipid IVA (Haemophilus), Kdo transfer to lipid IVA (P. gingivalis), Kdo transfer to lipid IVA (P. putida), Kdo transfer to lipid IVA (Vibrio cholerae serogroup O1 El Tor), Kdo8N transfer to lipid IVA, lacto-series glycosphingolipids biosynthesis, lipid A-core biosynthesis (P. gingivalis), methylerythritol phosphate pathway I, methylerythritol phosphate pathway II, mucin core 1 and core 2 O-glycosylation, neolacto-series glycosphingolipids biosynthesis, nucleoside and nucleotide degradation (archaea), palmitoyl ethanolamide biosynthesis, phosalacine biosynthesis, phosphatidylcholine biosynthesis I, phosphatidylcholine biosynthesis II, phosphatidylcholine biosynthesis III, phosphatidylcholine biosynthesis IV, phosphatidylcholine biosynthesis VI, phosphatidylcholine resynthesis via glycerophosphocholine, phosphatidylethanolamine biosynthesis II, phosphatidylglycerol biosynthesis I, phosphatidylglycerol biosynthesis II, phosphatidylinositol biosynthesis I (bacteria), phosphatidylinositol biosynthesis II (eukaryotes), phosphatidylserine and phosphatidylethanolamine biosynthesis I, phosphinothricin tripeptide biosynthesis, plasmalogen biosynthesis I (aerobic), poly(3-O-beta-D-glucopyranosyl-N-acetylgalactosamine 1-phosphate) wall teichoic acid biosynthesis, poly(glycerol phosphate) wall teichoic acid biosynthesis, poly(ribitol phosphate) wall teichoic acid biosynthesis I (B. subtilis), poly(ribitol phosphate) wall teichoic acid biosynthesis II (S. aureus), pyrimidine ribonucleosides salvage I, ricinoleate biosynthesis, superpathway of phospholipid biosynthesis II (plants), terminal O-glycans residues modification (via type 2 precursor disaccharide), type I lipoteichoic acid biosynthesis (S. aureus), type IV lipoteichoic acid biosynthesis (S. pneumoniae), UTP and CTP dephosphorylation I, UTP and CTP dephosphorylation II

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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 (18 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 (123 results)

top print hide

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

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

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

2.7.8.48

CDP-ethanolamine + a ceramide = a ceramide phosphorylethanolamine + CMP

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

3.6.1.13

CDP-choline + H2O = CMP + phosphocholine

9DT6, 3D-view

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 (162 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

722513, 722511

2.7.7.19

ATP + CMP = diphosphate + ?

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

a ceramide phosphorylethanolamine + CMP = CDP-ethanolamine + a ceramide

766268

2.7.8.5

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

CMP + H2O = cytidine + 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, 288999, 289003, 289005, 288998, 289018, 289004

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 (645 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

2.4.1.9

CMP-sialic acid + lactosylceramide = CMP + ganglioside GM3

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, -

2.7.6.1

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

642716, 642729, 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

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

3.1.3.97

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

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

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

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

Inhibitor in Enzyme-catalyzed Reactions (95 results)

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1.1.1.205

25% inhibition at 0.6 mM

5 mM, 22% inhibition

45% residual activity at 10 mg/ml

less effective than CTP

636800

2.4.3.4

less effective than CTP

50 mM, strong inhibition

strong

weak inhibition

10-15% inhibition at 5 mM

inhibits uridylyl removing activity

643534, 643540, 643541

2.7.8.1

4 entries

2.7.8.14

645344, 645346, 645347

2.7.8.2

4 entries

2.7.8.4

competitive inhibition to CDPethanolamine, non-competitive inhibition to L-serine

1 mM: 1% inhibition

uncompetitive inhibitor

209484, 209485, 209492

3.5.4.5

4 entries

3.6.1.16

no inhibitory effect even at high concentrations

slight inhibition

no inhibition

complete inhibition at 0.5 mM

weak

3D Structure of Enzyme-Ligand-Complex (PDB) (704 results)

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (24 results)

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2.1.2.B2

0.047

at pH 7.5 and 37°C

758390

2.4.2.57

39.1

pH 7.5, 85°C

39.18

pH 7, 25°C

768788

3.1.3.5

202

37°C, pH not specified in the publication

729593

K_M Value (87 results)

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1.8.99.2

3.1

reaction with cytochrome c

393940

2.1.2.B2

0.0719

at pH 7.5 and 37°C

758390

2.4.2.57

6.2

pH 7.5, 85°C

0.00017

0.19

17.45

pH 7, 25°C

0.14

pH 7.0, 37°C

650635

K_i Value (16 results)

0.18

5.6

pH 7.5, 25°C

643306

2.7.7.43

0.5

pH 9.0, 37°C

645263

3.1.13.4

0.7

at pH 7.0, 30°C

707501

3.1.30.2

0.0862

pH 8.5, 37°C

0.447

pH 7.6, 37°C

666478

6.3.2.5

4.69

pH 7.6, 37°C

702454

6.3.2.51

4.69

at pH 7.6 and 37°C

702454

IC₅₀ Value (1 result)

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2.4.3.9

0.0887

pH 6.5, 23°C

756067

References & Links

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Show Reference (481 entries)

Links to other databases for cytidine 5'-monophosphate

Ligand cytidine 5'-monophosphate

Basic Ligand Information

Related pathways

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (18 results)

In Vivo Product in Enzyme-catalyzed Reactions (123 results)

Substrate in Enzyme-catalyzed Reactions (162 results)

Product in Enzyme-catalyzed Reactions (645 results)

Enzyme Cofactor/Cosubstrate (3 results)

Activator in Enzyme-catalyzed Reactions (11 results)

Inhibitor in Enzyme-catalyzed Reactions (95 results)

3D Structure of Enzyme-Ligand-Complex (PDB) (704 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (24 results)

KM Value (87 results)

Ki Value (16 results)

IC50 Value (1 result)

References & Links

Literature References (481)

Links to other databases for cytidine 5'-monophosphate

k_cat Value (Turnover Number) (24 results)

K_M Value (87 results)

K_i Value (16 results)

IC₅₀ Value (1 result)