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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-19 23:57:54 UTC
NP-MRD IDNP0000183
Secondary Accession NumbersNone
Natural Product Identification
Common NameCytidine triphosphate
DescriptionCytidine triphosphate (CTP), also known as 5'-CTP, is pyrimidine nucleoside triphosphate. Formally, CTP is an ester of cytidine and triphosphoric acid. It 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. CTP, much like ATP, consists of a base (cytosine), a ribose sugar, and three phosphate groups. CTP is a high-energy molecule similar to ATP, but its role as an energy coupler is limited to a much smaller subset of metabolic reactions. CTP exists in all living species, ranging from bacteria to plants to humans and is used in the synthesis of RNA via RNA polymerase. Another enzyme known as cytidine triphosphate synthetase (CTPS) mediates the conversion of uridine triphosphate (UTP) into cytidine triphosphate (CTP) which is the rate-limiting step of de novo CTP biosynthesis. CTPS catalyzes a complex set of reactions that include the ATP-dependent transfer of the amide nitrogen from glutamine (i.E., Glutaminase reaction) to the C-4 position of UTP to generate CTP. GTP stimulates the glutaminase reaction by accelerating the formation of a covalent glutaminyl enzyme intermediate. CTPS activity regulates the intracellular rates of RNA synthesis, DNA synthesis, and phospholipid synthesis. CTPS is an established target for a number of antiviral, antineoplastic, and antiparasitic drugs. CTP also acts as an inhibitor of the enzyme known as aspartate carbamoyltransferase, which is used in pyrimidine biosynthesis. CTP also reacts with nitrogen-containing alcohols to form coenzymes that participate in the formation of phospholipids. In particular, CTP is the direct precursor of the activated, phospholipid pathway intermediates CDP-diacylglycerol, CDP-choline, and CDP-ethanolamine ((PMID: 18439916 ). CDP-diacylglycerol is the source of the phosphatidyl moiety for phosphatidylserine, phosphatidylethanolamine, and phosphatidylcholine (synthesized by way of the CDP-diacylglycerol pathway) as well as phosphatidylglycerol, cardiolipin, and phosphatidylinositol (PMID: 18439916 ).
Structure
Thumb
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 Mass483.1563 Da
Monoisotopic Mass482.98451 Da
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
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 1H] 2D NMR Spectrum (experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
  • All
  • Species Where Detected
    Species NameSourceReference
    Escherichia coliKNApSAcK Database
    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 ParentsNot Available
    SubstituentsNot Available
    Molecular FrameworkAromatic heteromonocyclic compounds
    External DescriptorsNot Available
    Physical Properties
    StateSolid
    Experimental Properties
    PropertyValueReference
    Melting Point215 - 218 °CNot Available
    Boiling PointNot AvailableNot Available
    Water Solubility1000000 mg/L @ 25 °C (est)The Good Scents Company Information System
    LogPNot AvailableNot Available
    Predicted Properties
    PropertyValueSource
    Water Solubility11.2 g/LALOGPS
    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
    External Links
    HMDB IDHMDB0000082
    DrugBank IDDB02431
    Phenol Explorer Compound IDNot Available
    FoodDB IDFDB030748
    KNApSAcK IDC00019639
    Chemspider ID5941
    KEGG Compound IDC00063
    BioCyc IDCTP
    BiGG ID33710
    Wikipedia LinkCytidine triphosphate
    METLIN ID5136
    PubChem Compound6176
    PDB IDNot Available
    ChEBI ID17677
    Good Scents IDrw1278391
    References
    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 ]
    7. Chang YF, Carman GM: CTP synthetase and its role in phospholipid synthesis in the yeast Saccharomyces cerevisiae. Prog Lipid Res. 2008 Sep;47(5):333-9. doi: 10.1016/j.plipres.2008.03.004. Epub 2008 Apr 7. [PubMed:18439916 ]