Ligand cytidine 5'-monophosphate

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Basic Ligand Information

Molecular Structure
Picture of cytidine 5'-monophosphate (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
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
Pathway Source
Pathways
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 more


Show all pahtways known for Show all BRENDA pathways known for cytidine 5'-monophosphate

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (16 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
5,10-methylenetetrahydrofolate + H2O + cytidylate = tetrahydrofolate + 5-hydroxymethylcytidylate
show the reaction diagram
-
CMP + phosphatidylcholine = ?
show the reaction diagram
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CMP + diphosphate + N-[(R)-4'-phosphopantothenoyl]-L-cysteine = CTP + (R)-4'-phosphopantothenate + L-cysteine
show the reaction diagram

In Vivo Product in Enzyme-catalyzed Reactions (132 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
acetyl-CoA + CMP-N-acetylneuraminate = CoA + N-acetyl-9-O-acetylneuraminate + CMP
show the reaction diagram
-
-
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
show the reaction diagram
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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
show the reaction diagram
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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
show the reaction diagram
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CMP-N-acetyl-beta-neuraminate + ganglioside GM1a = CMP + ganglioside GD1a
show the reaction diagram
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CMP-N-acetylneuraminate + glycano-1,3-(N-acetyl-alpha-D-galactosaminyl)-glycoprotein = CMP + glycano-(2,6-alpha-N-acetylneuraminyl)-(N-acetyl-D-galactosaminyl)-glycoprotein
show the reaction diagram
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CMP-N-acetylneuraminate + 1,2-diacyl-3-beta-D-galactosyl-sn-glycerol = CMP + 1,2-diacyl-3-[3-(alpha-D-N-acetylneuraminyl)-beta-D-galactosyl]-sn-glycerol
show the reaction diagram
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cytidine + ATP = CMP + ADP
show the reaction diagram
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CDP-choline + sphingosine = CMP + sphingosylphosphorylcholine
show the reaction diagram
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CDP-glycerol + (glycerophosphate)n = CMP + (glycerophosphate)n+1
show the reaction diagram
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CDPribitol + (ribitol phosphate)n = CMP + (ribitol phosphate)n+1
show the reaction diagram
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CDP-choline + 1-alkenyl-2-acylglycerol = CMP + plasmenylcholine
show the reaction diagram
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CDP-diacylglycerol + choline = CMP + phosphatidylcholine
show the reaction diagram
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cytidine diphosphate choline + N-acyl-threo-trans-sphingosine = CMP + sphingomyelin
show the reaction diagram
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CDP-1L-myo-inositol + 1L-myo-inositol 1-phosphate = CMP + bis(1L-myo-inositol) 3,1'-phosphate 1-phosphate
show the reaction diagram
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CDP-2,3-bis-O-(phytanyl)-sn-glycerol + 1L-myo-inositol 1-phosphate = CMP + 1-archaetidyl-1D-myo-inositol 3-phosphate
show the reaction diagram
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CDP-ethanolamine + L-serine = CMP + L-serine-ethanolamine phosphate
show the reaction diagram
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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
show the reaction diagram
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CDP-diacylglycerol + 1L-myo-inositol 1-phosphate = CMP + 1-phosphatidyl-1D-myo-inositol 3-phosphate
show the reaction diagram
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CDP + H2O = CMP + phosphate
show the reaction diagram
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CDPglycerol + H2O = CMP + L-alpha-glycerophosphate
show the reaction diagram
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CDPdiacylglycerol + H2O = CMP + phosphatidate
show the reaction diagram
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CTP + H2O = CMP + diphosphate
show the reaction diagram
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CTP + (R)-4'-phosphopantothenate + L-cysteine = CMP + diphosphate + N-[(R)-4'-phosphopantothenoyl]-L-cysteine
show the reaction diagram
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CTP + (R)-4'-phosphopantothenate + L-cysteine = CMP + diphosphate + N-[(R)-4'-phosphopantothenoyl]-L-cysteine
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (154 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
CMP + reduced thioredoxin = dCMP + oxidized thioredoxin + H2O
show the reaction diagram
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5,10-methylenetetrahydrofolate + CMP = dihydrofolate + 5-methylcytidylate
show the reaction diagram
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5,10-methylenetetrahydrofolate + H2O + cytidylate = tetrahydrofolate + 5-hydroxymethylcytidylate
show the reaction diagram
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sucrose + CMP = D-fructose + CMP 1-glucoside
show the reaction diagram
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CMP + phosphate = cytosine + alpha-D-ribose 1,5-bisphosphate
show the reaction diagram
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CMP + trans-farnesyl diphosphate = GDP + trans-farnesyl triphosphate
show the reaction diagram
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CMP + [phosphate]n = CDP + [phosphate]n-1
show the reaction diagram
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ATP + CMP = diphosphate + ?
show the reaction diagram
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1-stearoyl-2-arachidonoylphosphatidylinositol + CMP = CDP-1-stearoyl-2-arachidonoylglycerol + myo-inositol
show the reaction diagram
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5'-CMP + H2O = cytidine + phosphate
show the reaction diagram
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CMP + H2O = cytosine + phosphate
show the reaction diagram
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5'-CMP + H2O = cytosine + ribose 5-phosphate
show the reaction diagram
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CMP + H2O = UMP + NH3
show the reaction diagram
-
cytidine-5'-monophosphate + H2O = ?
show the reaction diagram
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CMP + diphosphate + N-[(R)-4'-phosphopantothenoyl]-L-cysteine = CTP + (R)-4'-phosphopantothenate + L-cysteine
show the reaction diagram

Product in Enzyme-catalyzed Reactions (644 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
5,10-methylenetetrahydrofolate + 2'-deoxycytidine 5'-monophosphate = dihydrofolate + cytidine phosphate
show the reaction diagram
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acetyl-CoA + CMP-N-acetylneuraminate = CoA + N-acetyl-9-O-acetylneuraminate + CMP
show the reaction diagram
-
-
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
show the reaction diagram
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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
show the reaction diagram
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AMP + cytidine = adenosine + cytidine 5'-phosphate
show the reaction diagram
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CDP + D-glucose = CMP + D-glucose 6-phosphate
show the reaction diagram
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ATP + cytidine = ADP + CMP
show the reaction diagram
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CDP + CDP = CTP + CMP
show the reaction diagram
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CTP + D-ribose 5-phosphate = CMP + 5-phospho-alpha-D-ribose 1-diphosphate
show the reaction diagram
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CTP + thiamine = CMP + thiamine diphosphate
show the reaction diagram
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CDP-glycerol + 1L-myo-inositol 1-phosphate = CMP + 1-(1X-glyceryl) myo-inosityl phosphate 3-phosphate
show the reaction diagram
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CDP-choline + sphingosine = CMP + sphingosylphosphorylcholine
show the reaction diagram
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CDP-choline + 1-alkenyl-2-acylglycerol = CMP + plasmenylcholine
show the reaction diagram
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CDP-diacylglycerol + choline = CMP + phosphatidylcholine
show the reaction diagram
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CDP-ethanolamine + L-serine = CMP + L-serine-ethanolamine phosphate
show the reaction diagram
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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
show the reaction diagram
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UDP-D-galactose + phosphoryl-polyprenol = galactosyl-diphospho-polyprenol + CMP
show the reaction diagram
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single-stranded oligodeoxycytidylate + H2O = single-stranded oligodeoxycytidylate + cytidyl 5'-monophosphate
show the reaction diagram
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CDP + H2O = CMP + phosphate
show the reaction diagram
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CDP + H2O = CMP + phosphate
show the reaction diagram
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cytidine 3',5'-bisphosphate + H2O = cytidine 5'-phosphate + phosphate
show the reaction diagram
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glucose + CDP = glucose 6-phosphate + CMP
show the reaction diagram
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polycytosylic acid + H2O = 5'-CMP + 5'-phosphooligonucleotides
show the reaction diagram
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CDP + H2O = CMP + phosphate
show the reaction diagram
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3',5'-cCMP + H2O = 5'-CMP
show the reaction diagram
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CDP + H2O = CMP + phosphate
show the reaction diagram
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CMP-N-acylneuraminate + H2O = CMP + N-acylneuraminate
show the reaction diagram
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CTP + H2O = CMP + diphosphate
show the reaction diagram
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CDP + H2O = CMP + phosphate
show the reaction diagram
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CDPglycerol + H2O = CMP + L-alpha-glycerophosphate
show the reaction diagram
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cytidine 5'-p-nitrophenylphosphate + H2O = p-nitrophenol + CMP
show the reaction diagram
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7-methylguanosine(5')triphospho(5')cytosine + H2O = 7-methylguanosine(5')monophosphate + CDP + CMP + 7-methylguanosine(5')diphosphate
show the reaction diagram
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adenosine 5'-P(1)-triphosphate-P(3)-5''-cytidine + H2O = ADP + CMP + CDP + AMP
show the reaction diagram
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CTP + H2O = CMP + diphosphate
show the reaction diagram
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CTP + H2O = CMP + diphosphate
show the reaction diagram
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CDP-2,3-di-O-phytanyl-sn-glycerol + 1D-myo-inositol 1-phosphate = archaetidylinositol phosphate + CMP
show the reaction diagram
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CTP + acetate + CoA = CMP + diphosphate + acetyl-CoA
show the reaction diagram
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CTP + ferulate + CoA = CMP + diphosphate + feruloyl-CoA
show the reaction diagram
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CTP + butyrate + CoA = CMP + diphosphate + butyryl-CoA
show the reaction diagram
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CTP + acetate + citrate (pro-3S)-lyase = CMP + diphosphate + citrate(pro-3S)-lyase
show the reaction diagram
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CTP + phytanate + CoA = CMP + diphosphate + phytanoyl-CoA
show the reaction diagram
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CTP + o-succinylbenzoate + CoA = CMP + diphosphate + o-succinylbenzoyl-CoA
show the reaction diagram
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CTP + 4-hydroxybenzoate + CoA = CMP + 4-hydroxybenzoyl-CoA + diphosphate
show the reaction diagram
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CTP + phenylacetate + CoA = CMP + diphosphate + phenylacetyl-CoA
show the reaction diagram
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3-hydroxypropanoate + CTP + coenzyme A = 3-hydroxypropanoyl-CoA + CMP + diphosphate
show the reaction diagram
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CTP + oxalate + CoA = CMP + diphosphate + oxalyl-CoA
show the reaction diagram
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CTP + (R)-pantoate + beta-alanine = CMP + diphosphate + (R)-pantothenate
show the reaction diagram
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CTP + L-His + beta-Ala = CMP + phosphate + carnosine
show the reaction diagram
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CTP + (R)-4'-phosphopantothenate + L-cysteine = CMP + diphosphate + N-[(R)-4'-phosphopantothenoyl]-L-cysteine
show the reaction diagram
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CTP + (R)-4'-phosphopantothenate + L-cysteine = CMP + diphosphate + N-[(R)-4'-phosphopantothenoyl]-L-cysteine
show the reaction diagram
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CTP + biotin + apo-[methylmalonyl-CoA:pyruvate carboxyltransferase] = CMP + diphosphate + [methylmalonyl-CoA:pyruvate carboxyltransferase]
show the reaction diagram
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CTP + L-Asp + L-Gln = CMP + diphosphate + Asn + Glu
show the reaction diagram
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CTP + RNA 3'-terminal-phosphate = CMP + diphosphate + RNA terminal-2',3'-cyclic-phosphate
show the reaction diagram
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Enzyme Cofactor/Cosubstrate (3 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
activates
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Activator in Enzyme-catalyzed Reactions (11 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
slight activation
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2',3'-cyclic nucleotide phosphodiesterase activity
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1 mM, 25% activation
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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
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25% activation at 1 mM
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Inhibitor in Enzyme-catalyzed Reactions (98 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
25% inhibition at 0.6 mM
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5 mM, 22% inhibition
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45% residual activity at 10 mg/ml
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less effective than CTP
50 mM, strong inhibition
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strong
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weak inhibition
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10-15% inhibition at 5 mM
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inhibits uridylyl removing activity
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competitive inhibition to CDPethanolamine, non-competitive inhibition to L-serine
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1 mM: 1% inhibition
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55.4% inhibition at 10 mM
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uncompetitive inhibitor
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no inhibitory effect even at high concentrations
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slight inhibition
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no inhibition
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complete inhibition at 0.5 mM
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weak
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3D Structure of Enzyme-Ligand-Complex (PDB) (62 results)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (24 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
39.1
-
pH 7.5, 85°C
3.33
-
synthesis of a copolymer of cytidylic acid
303
-
37°C, pH6
202
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37°C, pH not specified in the publication

KM Value (87 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
3.1
-
reaction with cytochrome c
6.2
-
pH 7.5, 85°C