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Human Metabolome Database Version 3.5

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Showing metabocard for Cytidine triphosphate (HMDB00082)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:07:52 -0700
HMDB ID HMDB00082
Secondary Accession Numbers None
Metabolite Identification
Common Name Cytidine triphosphate
Description Cytidine 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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C9H16N3O14P3
Average Molecular Weight 483.1563
Monoisotopic Molecular Weight 482.984511771
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 Number 65-47-4
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 Key PCDQPRRSZKQHHS-XVFCMESISA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Nucleosides, Nucleotides, and Analogues
Class Pyrimidine Nucleotides
Sub Class Pyrimidine 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 Parent Pyrimidine Ribonucleoside Triphosphates
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Aminophosphonate metabolism
  • Component of Aminosugars metabolism
  • Component of Glycerophospholipid metabolism
  • Component of Pyrimidine metabolism
Application Not Available
Cellular locations
  • Cytoplasm
  • Mitochondria
  • Nucleus
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 215 - 218 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 11.2 g/L ALOGPS
LogP -0.34 ALOGPS
LogP -4.3 ChemAxon
LogS -1.64 ALOGPS
pKa (strongest acidic) 0.91 ChemAxon
pKa (strongest basic) -0.54 ChemAxon
Hydrogen Acceptor Count 13 ChemAxon
Hydrogen Donor Count 7 ChemAxon
Polar Surface Area 268.2 A2 ChemAxon
Rotatable Bond Count 8 ChemAxon
Refractivity 87.16 ChemAxon
Polarizability 35.87 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -3 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
[1H,1H] 2D NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
  • Nucleus
Biofluid Locations
  • Cellular Cytoplasm
Tissue Location
  • All Tissues
Pathways
Name SMPDB Link KEGG Link
Pyrimidine Metabolism SMP00046 map00240 Link_out
Transcription/Translation SMP00019 Not Available
DNA Replication Fork SMP00477 Not Available
Amino Sugar Metabolism SMP00045 map00520 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Cellular Cytoplasm Detected and Quantified
Article_icon
0 uM Adult (>18 years old) Both Normal Not Available
Cellular Cytoplasm Detected and Quantified
Article_icon
10 uM Adult (>18 years old) Both Normal Not Available
Cellular Cytoplasm Detected and Quantified
Article_icon
28 uM Adult (>18 years old) Both Normal Not Available
Cellular Cytoplasm Detected and Quantified
Article_icon
15 uM Adult (>18 years old) Both Normal Not Available
Cellular Cytoplasm Detected and Quantified
Article_icon
23 uM Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID DB02431 Link_out
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB012833
KNApSAcK ID C00019639 Link_out
Chemspider ID 5941 Link_out
KEGG Compound ID C00063 Link_out
BioCyc ID CTP Link_out
BiGG ID 33710 Link_out
Wikipedia Link Cytidine triphosphate Link_out
NuGOwiki Link HMDB00082 Link_out
Metagene Link HMDB00082 Link_out
METLIN ID 5136 Link_out
PubChem Compound 6176 Link_out
PDB ID CTP Link_out
ChEBI ID 17677 Link_out
References
Synthesis Reference Simon, 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) Download (PDF)
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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
Enzymes
Name: Ectonucleoside triphosphate diphosphohydrolase 1
Reactions:
  • ATP + 2 H2O = AMP + 2 phosphate [RN:R00085]
Gene Name: ENTPD1
Uniprot ID: P49961 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Soluble calcium-activated nucleotidase 1
Reactions:
  • a nucleoside diphosphate + H2O = a nucleotide + phosphate [RN:R00329]
Gene Name: CANT1
Uniprot ID: Q8WVQ1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Ectonucleoside triphosphate diphosphohydrolase 3
Reactions:
  • ATP + 2 H2O = AMP + 2 phosphate [RN:R00085]
Gene Name: ENTPD3
Uniprot ID: O75355 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Nucleoside diphosphate kinase, mitochondrial
Reactions:
  • ATP + nucleoside diphosphate = ADP + nucleoside triphosphate [RN:R00331]
Gene Name: NME4
Uniprot ID: O00746 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Nucleoside diphosphate kinase A
Reactions:
  • ATP + nucleoside diphosphate = ADP + nucleoside triphosphate [RN:R00331]
Gene Name: NME1
Uniprot ID: P15531 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Nucleoside diphosphate kinase 7
Reactions:
  • ATP + nucleoside diphosphate = ADP + nucleoside triphosphate [RN:R00331]
Gene Name: NME7
Uniprot ID: Q9Y5B8 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Nucleoside diphosphate kinase B
Reactions:
  • ATP + nucleoside diphosphate = ADP + nucleoside triphosphate [RN:R00331]
Gene Name: NME2
Uniprot ID: P22392 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Nucleoside diphosphate kinase 3
Reactions:
  • ATP + nucleoside diphosphate = ADP + nucleoside triphosphate [RN:R00331]
Gene Name: NME3
Uniprot ID: Q13232 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Nucleoside diphosphate kinase 6
Reactions:
  • ATP + nucleoside diphosphate = ADP + nucleoside triphosphate [RN:R00331]
Gene Name: NME6
Uniprot ID: O75414 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: N-acylneuraminate cytidylyltransferase
Reactions:
  • CTP + N-acylneuraminate = diphosphate + CMP-N-acylneuraminate [RN:R02599]
Gene Name: CMAS
Uniprot ID: Q8NFW8 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Inosine triphosphate pyrophosphatase
Reactions:
  • a nucleoside triphosphate + H2O = a nucleotide + diphosphate [RN:R01532]
Gene Name: ITPA
Uniprot ID: Q9BY32 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: CTP synthase 1
Reactions:
  • ATP + UTP + NH3 = ADP + phosphate + CTP [RN:R00571]
Gene Name: CTPS
Uniprot ID: P17812 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Choline-phosphate cytidylyltransferase B
Reactions:
  • CTP + choline phosphate = diphosphate + CDP-choline [RN:R01890]
Gene Name: PCYT1B
Uniprot ID: Q9Y5K3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 6-phosphofructokinase type C
Reactions:
  • ATP + D-fructose 6-phosphate = ADP + D-fructose 1,6-bisphosphate [RN:R00756]
Gene Name: PFKP
Uniprot ID: Q01813 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: DNA-directed RNA polymerase III subunit RPC4
Reactions:
    Gene Name: POLR3D
    Uniprot ID: P05423 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: DNA-directed RNA polymerase II subunit RPB2
    Reactions:
    • nucleoside triphosphate + RNAn = diphosphate + RNAn+1 [RN:R00444]
    Gene Name: POLR2B
    Uniprot ID: P30876 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: DNA-directed RNA polymerase II subunit RPB1
    Reactions:
    • nucleoside triphosphate + RNAn = diphosphate + RNAn+1 [RN:R00444]
    Gene Name: POLR2A
    Uniprot ID: P24928 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: DNA-directed RNA polymerase, mitochondrial
    Reactions:
    • nucleoside triphosphate + RNAn = diphosphate + RNAn+1 [RN:R00444]
    Gene Name: POLRMT
    Uniprot ID: O00411 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: DNA-directed RNA polymerase I subunit RPA2
    Reactions:
    • nucleoside triphosphate + RNAn = diphosphate + RNAn+1 [RN:R00444]
    Gene Name: POLR1B
    Uniprot ID: Q9H9Y6 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: DNA-directed RNA polymerase III subunit RPC7
    Reactions:
      Gene Name: POLR3G
      Uniprot ID: O15318 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Phosphatidate cytidylyltransferase 2
      Reactions:
      • CTP + phosphatidate = diphosphate + CDP-diacylglycerol [RN:R01799]
      Gene Name: CDS2
      Uniprot ID: O95674 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: DNA-directed RNA polymerase III subunit RPC2
      Reactions:
      • nucleoside triphosphate + RNAn = diphosphate + RNAn+1 [RN:R00444]
      Gene Name: POLR3B
      Uniprot ID: Q9NW08 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Choline-phosphate cytidylyltransferase A
      Reactions:
      • CTP + choline phosphate = diphosphate + CDP-choline [RN:R01890]
      Gene Name: PCYT1A
      Uniprot ID: P49585 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: DNA-directed RNA polymerase I subunit RPA49
      Reactions:
        Gene Name: POLR1E
        Uniprot ID: Q9GZS1 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: 6-phosphofructokinase, liver type
        Reactions:
        • ATP + D-fructose 6-phosphate = ADP + D-fructose 1,6-bisphosphate [RN:R00756]
        Gene Name: PFKL
        Uniprot ID: P17858 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: DNA-directed RNA polymerase III subunit RPC8
        Reactions:
          Gene Name: POLR3H
          Uniprot ID: Q9Y535 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: DNA-directed RNA polymerase III subunit RPC10
          Reactions:
            Gene Name: POLR3K
            Uniprot ID: Q9Y2Y1 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: 6-phosphofructokinase, muscle type
            Reactions:
            • ATP + D-fructose 6-phosphate = ADP + D-fructose 1,6-bisphosphate [RN:R00756]
            Gene Name: PFKM
            Uniprot ID: P08237 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: Pyruvate kinase isozymes M1/M2
            Reactions:
            • ATP + pyruvate = ADP + phosphoenolpyruvate [RN:R00200]
            Gene Name: PKM2
            Uniprot ID: P14618 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: Phosphatidate cytidylyltransferase 1
            Reactions:
            • CTP + phosphatidate = diphosphate + CDP-diacylglycerol [RN:R01799]
            Gene Name: CDS1
            Uniprot ID: Q92903 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: Pyruvate kinase isozymes R/L
            Reactions:
            • ATP + pyruvate = ADP + phosphoenolpyruvate [RN:R00200]
            Gene Name: PKLR
            Uniprot ID: P30613 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: Uridine-cytidine kinase 2
            Reactions:
            • ATP + uridine = ADP + UMP [RN:R00964]
            Gene Name: UCK2
            Uniprot ID: Q9BZX2 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: Phosphopantothenoylcysteine synthetase
            Reactions:
            • --- - CTP + (R)-4'-phosphopantothenate + L-cysteine = CMP + diphosphate + N-[(R)-4'-phosphopantothenoyl]-L-cysteine [RN:R04231]
            Gene Name: PPCS
            Uniprot ID: Q9HAB8 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: CAD protein
            Reactions:
            • (1) 2 ATP + L-glutamine + HCO3- + H2O = 2 ADP + phosphate + L-glutamate + carbamoyl phosphate [RN:R00575]
            • (2) L-glutamine + H2O = L-glutamate + NH3 [RN:R00256]
            • (3) 2 ATP + HCO3- = 2 ADP + phosphate + carbamoyl phosphate [RN:R07641]
            Gene Name: CAD
            Uniprot ID: P27708 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: CTP synthase 2
            Reactions:
            • ATP + UTP + NH3 = ADP + phosphate + CTP [RN:R00571]
            Gene Name: CTPS2
            Uniprot ID: Q9NRF8 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: Ectonucleoside triphosphate diphosphohydrolase 8
            Reactions:
            • ATP + 2 H2O = AMP + 2 phosphate [RN:R00085]
            Gene Name: ENTPD8
            Uniprot ID: Q5MY95 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: Putative nucleoside diphosphate kinase
            Reactions:
            • ATP + nucleoside diphosphate = ADP + nucleoside triphosphate [RN:R00331]
            Gene Name: NME2P1
            Uniprot ID: O60361 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: DNA-directed RNA polymerase III subunit RPC1
            Reactions:
            • nucleoside triphosphate + RNAn = diphosphate + RNAn+1 [RN:R00444]
            Gene Name: POLR3A
            Uniprot ID: O14802 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: DNA-directed RNA polymerase I subunit RPA1
            Reactions:
            • nucleoside triphosphate + RNAn = diphosphate + RNAn+1 [RN:R00444]
            Gene Name: POLR1A
            Uniprot ID: O95602 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: Zinc ribbon domain containing 1
            Reactions:
              Gene Name: ZNRD1
              Uniprot ID: Q2L6J2 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: DNA-directed RNA polymerases I and III subunit RPAC2
              Reactions:
                Gene Name: POLR1D
                Uniprot ID: Q9Y2S0 Link_out
                Protein Sequence: FASTA
                Gene Sequence: FASTA
                Name: DNA-directed RNA polymerase
                Reactions:
                • nucleoside triphosphate + RNAn = diphosphate + RNAn+1 [RN:R00444]
                Gene Name: DKFZp686D10173
                Uniprot ID: Q7Z3R8 Link_out
                Protein Sequence: FASTA
                Gene Sequence: FASTA
                Name: DNA-directed RNA polymerase III subunit RPC7-like
                Reactions:
                  Gene Name: POLR3GL
                  Uniprot ID: Q9BT43 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: POLR1C protein
                  Reactions:
                    Gene Name: POLR1C
                    Uniprot ID: Q96HT3 Link_out
                    Protein Sequence: FASTA
                    Gene Sequence: FASTA