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Showing metabocard for Cytidine triphosphate (BMDB0000082)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (6) Show 6 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:19:26 UTC
Update Date2020-05-21 16:29:00 UTC
BMDB IDBMDB0000082
Secondary Accession Numbers
  • BMDB00082
Metabolite Identification
Common NameCytidine triphosphate
DescriptionCytidine triphosphate, also known as 5'-CTP or H4CTP, belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups. Cytidine triphosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). Cytidine triphosphate exists in all living species, ranging from bacteria to humans.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
5'-CTPChEBI
Cytidine 5'-triphosphateChEBI
CYTIDINE-5'-triphosphATEChEBI
H4CTPChEBI
Cytidine 5'-triphosphoric acidGenerator
CYTIDINE-5'-triphosphoric acidGenerator
Cytidine triphosphoric acidGenerator
5'-(Tetrahydrogen triphosphate) cytidineHMDB
CTPHMDB
Cytidine 3'-triphosphateHMDB
Cytidine 5'-(tetrahydrogen triphosphate)HMDB
Cytidine 5-prime-triphosphateHMDB
Cytidine monoHMDB
Cytidine mono(tetrahydrogen triphosphate) (ester)HMDB
Deoxycytosine triphosphateHMDB
Triphosphate, cytidineHMDB
CRPPPHMDB
Magnesium CTPHMDB
MG CTPHMDB
Chemical FormulaC9H16N3O14P3
Average Molecular Weight483.1563
Monoisotopic Molecular Weight482.984511771
IUPAC Name({[({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
Traditional NameCTP
CAS Registry Number65-47-4
SMILES
NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O
InChI Identifier
InChI=1S/C9H16N3O14P3/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(24-8)3-23-28(19,20)26-29(21,22)25-27(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H,21,22)(H2,10,11,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1
InChI KeyPCDQPRRSZKQHHS-XVFCMESISA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPentose phosphates
Alternative Parents
Substituents
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Hydroxypyrimidine
  • Monoalkyl phosphate
  • Hydropyrimidine
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Phosphoric acid ester
  • Pyrimidine
  • Heteroaromatic compound
  • Tetrahydrofuran
  • 1,2-diol
  • Secondary alcohol
  • Azacycle
  • Oxacycle
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
  • Nucleus
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point215 - 218 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.34ALOGPS
logP-4.1ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)0.94ChemAxon
pKa (Strongest Basic)-0.076ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area268.2 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity87.16 m³·mol⁻¹ChemAxon
Polarizability35.87 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002b-8965400000-028238d320c37d90d959View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-03l3-4529211000-fc9c3bce80ab4bd56becView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00b9-5685900000-b067d3b0af4c194d5224View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-0309200000-33e695326ec0d28103b4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-057j-1926700000-417741bbe965170223c0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 10V, negativesplash10-001i-0201900000-d0f4b76212c986ba5256View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 15V, negativesplash10-053r-0602900000-3b15e1314bb085815ee1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 17V, negativesplash10-053r-0913800000-a9781bf9478c1556ea6fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 20V, negativesplash10-0a59-1903500000-ca05dcfb3a7e6249de5fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 23V, negativesplash10-0a59-1912200000-ed35edf8dd897cfb189fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 25V, negativesplash10-0a4i-1912100000-02368a767858b532e343View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 27V, negativesplash10-0a4i-1901100000-7e158597e6539f859f18View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 30V, negativesplash10-0a4i-2901000000-e6ffe54064813cca999aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 33V, negativesplash10-0a4i-2901000000-878ed1a77bece120cab0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 35V, negativesplash10-0a4i-3900000000-5609836a3262551e3f22View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 40V, negativesplash10-0a6r-4900000000-25ee9e049ac582f88998View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 45V, negativesplash10-0a6r-6900000000-df141b7c324466d11ca1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 33V, negativesplash10-001i-0109000000-e4e73cfc21a26fa84c94View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 18V, negativesplash10-001i-0100900000-1d8f337531a62dff2aefView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 23V, negativesplash10-053r-0703900000-43af4aa75af7c1b90a19View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 29V, negativesplash10-0a4i-0902200000-9cabc619fb140d01b9d7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0901100000-c35d289f50f6f03e2607View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-2901000000-52ceb0833c1f651ee73eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-5900000000-b2b882bb438556aea202View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01q9-0520900000-0e5b8be0fa0c2178439bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bwi-9660200000-4db67ca241ce3068a27fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9200000000-1f093b0fe69d03ecea98View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
  • Nucleus
Biospecimen Locations
  • All Tissues
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000082
DrugBank IDDB02431
Phenol Explorer Compound IDNot Available
FooDB IDFDB030748
KNApSAcK IDC00019639
Chemspider ID5941
KEGG Compound IDC00063
BioCyc IDCTP
BiGG ID33710
Wikipedia LinkCytidine triphosphate
METLIN ID5136
PubChem Compound6176
PDB IDNot Available
ChEBI ID17677
References
Synthesis ReferenceSimon, Ethan S.; Bednarski, Mark D.; Whitesides, George M. Synthesis of CMP-NeuAc from N-acetylglucosamine: generation of CTP from CMP using adenylate kinase. Journal of the American Chemical Society (1988), 110(21), 7159-63.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Phosphatidate cytidylyltransferase 2
General function:
Lipid transport and metabolism
Specific function:
Catalyzes the conversion of phosphatidic acid (PA) to CDP-diacylglycerol (CDP-DAG), an essential intermediate in the synthesis of phosphatidylglycerol, cardiolipin and phosphatidylinositol (By similarity). Exhibits specificity for the nature of the acyl chains at the sn-1 and sn-2 positions in the substrate, PA and the preferred acyl chain composition is 1-stearoyl-2-arachidonoyl-sn-phosphatidic acid (By similarity). Plays an important role in regulating the growth and maturation of lipid droplets which are storage organelles at the center of lipid and energy homeostasis (By similarity).
Gene Name:
CDS2
Uniprot ID:
A0JNC1
Molecular weight:
51357.0
Reactions
Cytidine triphosphate + 1,2-Diacyl-sn-glycerol 3-phosphate → Pyrophosphate + a CDP-diacylglyceroldetails
Cytidine triphosphate + PA(16:0/18:1(11Z)) → Pyrophosphate + CDP-DG(16:0/18:1(11Z))details
Cytidine triphosphate + PA(18:1(9Z)/18:1(9Z)) → Pyrophosphate + CDP-DG(18:1(9Z)/18:1(9Z))details
Cytidine triphosphate + PA(18:2(9Z,12Z)/18:2(9Z,12Z)) → Pyrophosphate + CDP-DG(18:2(9Z,12Z)/18:2(9Z,12Z))details
Enzyme Details
2. Ethanolamine-phosphate cytidylyltransferase
General function:
Cell wall/membrane/envelope biogenesis
Specific function:
Plays an important role in the biosynthesis of the phospholipid phosphatidylethanolamine. Catalyzes the formation of CDP-ethanolamine (By similarity).
Gene Name:
PCYT2
Uniprot ID:
Q5EA75
Molecular weight:
44158.0
Reactions
Cytidine triphosphate + Phosphorylcholine → Pyrophosphate + Citicolinedetails
Cytidine triphosphate + O-Phosphoethanolamine → Pyrophosphate + CDP-Ethanolaminedetails
Enzyme Details
3. Nucleoside diphosphate kinase 7
General function:
Nucleotide transport and metabolism
Specific function:
Major role in the synthesis of nucleoside triphosphates other than ATP. The ATP gamma phosphate is transferred to the NDP beta phosphate via a ping-pong mechanism, using a phosphorylated active-site intermediate (By similarity).
Gene Name:
NME7
Uniprot ID:
Q5E9Y9
Molecular weight:
42599.0
Reactions
Cytidine triphosphate + ADP → CDP + Adenosine triphosphatedetails
Enzyme Details
4. N-acylneuraminate cytidylyltransferase
General function:
Involved in N-acylneuraminate cytidylyltransferase acti
Specific function:
Catalyzes the activation of N-acetylneuraminic acid (NeuNAc) to cytidine 5'-monophosphate N-acetylneuraminic acid (CMP-NeuNAc), a substrate required for the addition of sialic acid. Has some activity toward NeuNAc, N-glycolylneuraminic acid (Neu5Gc) or 2-keto-3-deoxy-D-glycero-D-galacto-nononic acid (KDN) (By similarity).
Gene Name:
CMAS
Uniprot ID:
Q3SZM5
Molecular weight:
48438.0
Reactions
N-Acetylneuraminic acid + Cytidine triphosphate → Cytidine monophosphate N-acetylneuraminic acid + Pyrophosphatedetails
Enzyme Details
5. CTP synthase 2
General function:
Nucleotide transport and metabolism
Specific function:
Catalyzes the ATP-dependent amination of UTP to CTP with either L-glutamine or ammonia as the source of nitrogen. Constitutes the rate-limiting enzyme in the synthesis of cytosine nucleotides (By similarity).
Gene Name:
CTPS2
Uniprot ID:
Q1RMS2
Molecular weight:
65481.0
Reactions
Uridine triphosphate + Adenosine triphosphate → Cytidine triphosphate + ADP + Hydrogen phosphate + dCTPdetails
Enzyme Details
6. Calcium activated nucleotidase 1
General function:
Not Available
Specific function:
Not Available
Gene Name:
CANT1
Uniprot ID:
E1BGL5
Molecular weight:
44706.0
Reactions
Cytidine triphosphate + Water → CDP + Hydrogen phosphatedetails