Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:07:52 UTC
HMDB IDHMDB00082
Secondary Accession NumbersNone
Metabolite Identification
Common NameCytidine triphosphate
DescriptionCytidine 5'-(tetrahydrogen triphosphate) or CTP is a cytosine nucleotide containing three phosphate groups esterified to a ribose moiety at the 5' position. CTP is integral to the synthesis or mRNA, rRNA and tRNA through RNA polymerases. Cytidine triphosphate (CTP) is also critical to the synthesis of phosphatidylcholine via the enzyme CTP: phosphocholine cytidyltransferase. This reaction is the rate-limiting step in the synthesis of phosphatidylcholine.
Structure
Thumb
Synonyms
  1. 5'-(Tetrahydrogen triphosphate) cytidine
  2. 5'-CTP
  3. CTP
  4. Cytidine 3'-triphosphate
  5. Cytidine 5'-(tetrahydrogen triphosphate)
  6. Cytidine 5'-triphosphate
  7. Cytidine 5'-triphosphoric acid
  8. Cytidine 5-Prime-Triphosphate
  9. Cytidine mono
  10. Cytidine mono(tetrahydrogen triphosphate) (ester)
  11. Cytidine Triphosphate
  12. Cytidine-5'-triphosphate
  13. Deoxycytosine triphosphate
  14. H4ctp
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 IUPAC Name({[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxyphosphonic acid
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
KingdomOrganic Compounds
Super ClassNucleosides, Nucleotides, and Analogues
ClassPyrimidine Nucleotides
Sub ClassPyrimidine Ribonucleotides
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
Substituents
  • 1,2 Diol
  • Aminopyrimidine
  • Glycosyl Compound
  • Hydropyrimidine
  • Monosaccharide Phosphate
  • N Glycosyl Compound
  • Organic Hypophosphite
  • Organic Phosphite
  • Organic Pyrophosphate
  • Oxolane
  • Pentose Monosaccharide
  • Phosphoric Acid Ester
  • Pyrimidine
  • Pyrimidone
  • Saccharide
  • Secondary Alcohol
Direct ParentPyrimidine Ribonucleoside Triphosphates
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Aminophosphonate metabolism
  • Component of Aminosugars metabolism
  • Component of Glycerophospholipid metabolism
  • Component of Pyrimidine metabolism
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
water solubility11.2 g/LALOGPS
logP-0.34ALOGPS
logP-4.3ChemAxon
logS-1.6ALOGPS
pKa (strongest acidic)0.91ChemAxon
pKa (strongest basic)-0.54ChemAxon
physiological charge-3ChemAxon
hydrogen acceptor count13ChemAxon
hydrogen donor count7ChemAxon
polar surface area268.2ChemAxon
rotatable bond count8ChemAxon
refractivity87.16ChemAxon
polarizability35.87ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
  • Nucleus
Biofluid Locations
  • Cellular Cytoplasm
Tissue Location
  • All Tissues
Pathways
NameSMPDB LinkKEGG Link
Amino Sugar MetabolismSMP00045map00520
DNA Replication ForkSMP00477Not Available
Pyrimidine MetabolismSMP00046map00240
Transcription/TranslationSMP00019Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
Cellular CytoplasmDetected and Quantified0 uMAdult (>18 years old)BothNormal
Cellular CytoplasmDetected and Quantified10 uMAdult (>18 years old)BothNormal
Cellular CytoplasmDetected and Quantified28 uMAdult (>18 years old)BothNormal
Cellular CytoplasmDetected and Quantified15 uMAdult (>18 years old)BothNormal
Cellular CytoplasmDetected and Quantified23 uMAdult (>18 years old)BothNormal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB02431
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB012833
KNApSAcK IDC00019639
Chemspider ID5941
KEGG Compound IDC00063
BioCyc IDCTP
BiGG ID33710
Wikipedia LinkCytidine triphosphate
NuGOwiki LinkHMDB00082
Metagene LinkHMDB00082
METLIN ID5136
PubChem Compound6176
PDB IDCTP
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 References
  1. Watanabe T, Oguchi K, Ebara S, Fukui T: Measurement of 3-hydroxyisovaleric acid in urine of biotin-deficient infants and mice by HPLC. J Nutr. 2005 Mar;135(3):615-8. Pubmed: 15735103
  2. Kondo T, Ohtsuka Y, Shimada M, Kawakami Y, Hiyoshi Y, Tsuji Y, Fujii H, Miwa S: Erythrocyte-oxidized glutathione transport in pyrimidine 5'-nucleotidase deficiency. Am J Hematol. 1987 Sep;26(1):37-45. Pubmed: 2888306
  3. Kallander CF, Gronowitz JS, Olding-Stenkvist E: Varicella zoster virus deoxythymidine kinase is present in serum before the onset of varicella. Scand J Infect Dis. 1989;21(3):255-7. Pubmed: 2547243
  4. de Korte D, Haverkort WA, van Gennip AH, Roos D: Nucleotide profiles of normal human blood cells determined by high-performance liquid chromatography. Anal Biochem. 1985 May 15;147(1):197-209. Pubmed: 4025817
  5. Verschuur AC, Brinkman J, Van Gennip AH, Leen R, Vet RJ, Evers LM, Voute PA, Van Kuilenburg AB: Cyclopentenyl cytosine induces apoptosis and increases cytarabine-induced apoptosis in a T-lymphoblastic leukemic cell-line. Leuk Res. 2001 Oct;25(10):891-900. Pubmed: 11532523
  6. Cornell RB, Northwood IC: Regulation of CTP:phosphocholine cytidylyltransferase by amphitropism and relocalization. Trends Biochem Sci. 2000 Sep;25(9):441-7. Pubmed: 10973058

Only showing the first 50 proteins. There are 65 proteins in total.

Enzymes

Gene Name:
ENTPD1
Uniprot ID:
P49961
Reactions
Cytidine triphosphate + Water unknown CDP + Phosphoric aciddetails
Gene Name:
ENTPD3
Uniprot ID:
O75355
Reactions
Cytidine triphosphate + Water unknown CDP + Phosphoric aciddetails
Gene Name:
NME4
Uniprot ID:
O00746
Reactions
Adenosine triphosphate + CDP unknown ADP + Cytidine triphosphatedetails
Gene Name:
NME1
Uniprot ID:
P15531
Reactions
Adenosine triphosphate + CDP unknown ADP + Cytidine triphosphatedetails
Gene Name:
NME7
Uniprot ID:
Q9Y5B8
Reactions
Adenosine triphosphate + CDP unknown ADP + Cytidine triphosphatedetails
Gene Name:
NME2
Uniprot ID:
P22392
Reactions
Adenosine triphosphate + CDP unknown ADP + Cytidine triphosphatedetails
Gene Name:
NME3
Uniprot ID:
Q13232
Reactions
Adenosine triphosphate + CDP unknown ADP + Cytidine triphosphatedetails
Gene Name:
NME6
Uniprot ID:
O75414
Reactions
Adenosine triphosphate + CDP unknown ADP + Cytidine triphosphatedetails
Gene Name:
CMAS
Uniprot ID:
Q8NFW8
Reactions
Cytidine triphosphate + N-acylneuraminate unknown Pyrophosphate + Cytidine monophosphate N-acetylneuraminic aciddetails
Cytidine triphosphate + N-Acetylneuraminic acid unknown Pyrophosphate + Cytidine monophosphate N-acetylneuraminic aciddetails
Cytidine triphosphate + N-Glycolylneuraminic acid unknown Pyrophosphate + CMP-N-glycoloylneuraminatedetails
Gene Name:
ITPA
Uniprot ID:
Q9BY32
Gene Name:
CTPS1
Uniprot ID:
P17812
Reactions
Adenosine triphosphate + Uridine triphosphate + Ammonia unknown ADP + Phosphoric acid + Cytidine triphosphatedetails
Adenosine triphosphate + Uridine triphosphate + L-Glutamine + Water unknown ADP + Phosphoric acid + Cytidine triphosphate + L-Glutamic aciddetails
Gene Name:
PCYT1B
Uniprot ID:
Q9Y5K3
Reactions
Cytidine triphosphate + Phosphorylcholine unknown Pyrophosphate + Citicolinedetails
Cytidine triphosphate + Phosphorylcholine unknown Pyrophosphate + CMP-N-trimethyl-2-aminoethylphosphonatedetails
Gene Name:
PFKP
Uniprot ID:
Q01813
Reactions
Cytidine triphosphate + D-Tagatose 6-phosphate unknown CDP + D-Tagatose 1,6-bisphosphatedetails
Gene Name:
POLR3D
Uniprot ID:
P05423
Reactions
Cytidine triphosphate + RNA unknown Pyrophosphate + RNAdetails
Gene Name:
POLR2B
Uniprot ID:
P30876
Reactions
Cytidine triphosphate + RNA unknown Pyrophosphate + RNAdetails
Gene Name:
PCYT2
Uniprot ID:
Q99447
Reactions
Cytidine triphosphate + O-Phosphoethanolamine unknown Pyrophosphate + CDP-Ethanolaminedetails
Cytidine triphosphate + Ciliatine unknown Pyrophosphate + CMP-2-aminoethylphosphonatedetails
Gene Name:
POLR2A
Uniprot ID:
P24928
Reactions
Cytidine triphosphate + RNA unknown Pyrophosphate + RNAdetails
Gene Name:
POLR1B
Uniprot ID:
Q9H9Y6
Reactions
Cytidine triphosphate + RNA unknown Pyrophosphate + RNAdetails
Gene Name:
POLR3G
Uniprot ID:
O15318
Reactions
Cytidine triphosphate + RNA unknown Pyrophosphate + RNAdetails
Gene Name:
CDS2
Uniprot ID:
O95674
Reactions
Cytidine triphosphate + phosphatidate unknown Pyrophosphate + CDP-diacylglyceroldetails
Cytidine triphosphate + Phosphatidate unknown Pyrophosphate + CDP-diacylglyceroldetails
Gene Name:
POLR3B
Uniprot ID:
Q9NW08
Reactions
Cytidine triphosphate + RNA unknown Pyrophosphate + RNAdetails
Gene Name:
PCYT1A
Uniprot ID:
P49585
Reactions
Cytidine triphosphate + Phosphorylcholine unknown Pyrophosphate + Citicolinedetails
Cytidine triphosphate + Phosphorylcholine unknown Pyrophosphate + CMP-N-trimethyl-2-aminoethylphosphonatedetails
Gene Name:
POLR1E
Uniprot ID:
Q9GZS1
Reactions
Cytidine triphosphate + RNA unknown Pyrophosphate + RNAdetails
Gene Name:
PFKL
Uniprot ID:
P17858
Reactions
Cytidine triphosphate + D-Tagatose 6-phosphate unknown CDP + D-Tagatose 1,6-bisphosphatedetails
Gene Name:
POLR3H
Uniprot ID:
Q9Y535
Reactions
Cytidine triphosphate + RNA unknown Pyrophosphate + RNAdetails
Gene Name:
POLR3K
Uniprot ID:
Q9Y2Y1
Reactions
Cytidine triphosphate + RNA unknown Pyrophosphate + RNAdetails
Gene Name:
PFKM
Uniprot ID:
P08237
Reactions
Cytidine triphosphate + D-Tagatose 6-phosphate unknown CDP + D-Tagatose 1,6-bisphosphatedetails
Gene Name:
PKM
Uniprot ID:
P14618
Gene Name:
CDS1
Uniprot ID:
Q92903
Reactions
Cytidine triphosphate + phosphatidate unknown Pyrophosphate + CDP-diacylglyceroldetails
Cytidine triphosphate + Phosphatidate unknown Pyrophosphate + CDP-diacylglyceroldetails
Gene Name:
PKLR
Uniprot ID:
P30613
Gene Name:
UCK2
Uniprot ID:
Q9BZX2
Gene Name:
PPCS
Uniprot ID:
Q9HAB8
Reactions
Cytidine triphosphate + D-4'-Phosphopantothenate + L-Cysteine unknown Cytidine monophosphate + Pyrophosphate + N-((R)-4'-phosphopantothenoyl)-L-cysteinedetails
Cytidine triphosphate + D-4'-Phosphopantothenate + L-Cysteine unknown Cytidine monophosphate + Pyrophosphate + 4-Phosphopantothenoylcysteinedetails
Gene Name:
CAD
Uniprot ID:
P27708
Gene Name:
CTPS2
Uniprot ID:
Q9NRF8
Reactions
Adenosine triphosphate + Uridine triphosphate + Ammonia unknown ADP + Phosphoric acid + Cytidine triphosphatedetails
Adenosine triphosphate + Uridine triphosphate + L-Glutamine + Water unknown ADP + Phosphoric acid + Cytidine triphosphate + L-Glutamic aciddetails
Gene Name:
ENTPD8
Uniprot ID:
Q5MY95
Reactions
Cytidine triphosphate + Water unknown CDP + Phosphoric aciddetails
Gene Name:
NME2P1
Uniprot ID:
O60361
Gene Name:
TRNT1
Uniprot ID:
Q96Q11
Reactions
A tRNA precursor + Cytidine triphosphate + Adenosine triphosphate unknown a tRNA with a 3' CCA end + Pyrophosphatedetails
tRNA precursor + Cytidine triphosphate + Adenosine triphosphate unknown tRNA with a 3' CCA end + Pyrophosphatedetails
tRNA precursor + Cytidine triphosphate unknown tRNA with a 3' cytidine + Pyrophosphatedetails
tRNA with a 3' cytidine + Cytidine triphosphate unknown tRNA with a 3' CC end + Pyrophosphatedetails
Gene Name:
DOLK
Uniprot ID:
Q9UPQ8
Reactions
Cytidine triphosphate + dolichol unknown CDP + Dolichol-20details
Gene Name:
POLR3A
Uniprot ID:
O14802
Reactions
Cytidine triphosphate + RNA unknown Pyrophosphate + RNAdetails
Gene Name:
POLR1A
Uniprot ID:
O95602
Reactions
Cytidine triphosphate + RNA unknown Pyrophosphate + RNAdetails
Gene Name:
ZNRD1
Uniprot ID:
Q2L6J2
Gene Name:
POLR1D
Uniprot ID:
Q9Y2S0
Reactions
Cytidine triphosphate + RNA unknown Pyrophosphate + RNAdetails
Gene Name:
DKFZp686D10173
Uniprot ID:
Q7Z3R8
Gene Name:
POLR3GL
Uniprot ID:
Q9BT43
Reactions
Cytidine triphosphate + RNA unknown Pyrophosphate + RNAdetails
Gene Name:
POLR1C
Uniprot ID:
Q96HT3
Gene Name:
NME5
Uniprot ID:
P56597
Reactions
Adenosine triphosphate + CDP unknown ADP + Cytidine triphosphatedetails
Gene Name:
ZNRD1
Uniprot ID:
Q9P1U0
Reactions
Cytidine triphosphate + RNA unknown Pyrophosphate + RNAdetails
Gene Name:
TWISTNB
Uniprot ID:
Q3B726
Reactions
Cytidine triphosphate + RNA unknown Pyrophosphate + RNAdetails

Only showing the first 50 proteins. There are 65 proteins in total.