You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2014-06-23 12:04:06 UTC
Update Date2019-07-23 07:17:04 UTC
HMDB IDHMDB0061723
Secondary Accession Numbers
  • HMDB61723
Metabolite Identification
Common NameCarbovir Triphosphate
DescriptionCarbovir Triphosphate, also known as CBV-TP, belongs to the class of organic compounds known as nucleoside and nucleotide analogues. These are analogues of nucleosides and nucleotides. These include phosphonated nucleosides, C-glycosylated nucleoside bases, analogues where the sugar unit is a pyranose, and carbocyclic nucleosides, among others. Carbovir Triphosphate is a moderately basic compound (based on its pKa). The organic triphosphate that is the 5'-triphosphate of (-)-carbovir. In humans, carbovir triphosphate is involved in abacavir action pathway.
Structure
Data?1563866224
Synonyms
ValueSource
(-)-Carbovir 5'-triphosphateChEBI
(-)-Carbovir triphosphateChEBI
(1S-cis)-Triphosphoric acid, p-((4-(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)-2-cyclopenten-1-yl)methyl) esterChEBI
Carbovir 5'-triphosphateChEBI
(-)-Carbovir 5'-triphosphoric acidGenerator
(-)-Carbovir triphosphoric acidGenerator
(1S-cis)-Triphosphate, p-((4-(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)-2-cyclopenten-1-yl)methyl) esterGenerator
Carbovir 5'-triphosphoric acidGenerator
Carbovir triphosphoric acidGenerator
CBV-TPHMDB
Chemical FormulaC11H16N5O11P3
Average Molecular Weight487.1929
Monoisotopic Molecular Weight487.005915915
IUPAC Name({[({[(1S,4R)-4-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)cyclopent-2-en-1-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
Traditional Namecarbovir triphosphate
CAS Registry NumberNot Available
SMILES
NC1=NC2=C(N=CN2[C@@H]2C[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C=C2)C(=O)N1
InChI Identifier
InChI=1S/C11H16N5O11P3/c12-11-14-9-8(10(17)15-11)13-5-16(9)7-2-1-6(3-7)4-25-29(21,22)27-30(23,24)26-28(18,19)20/h1-2,5-7H,3-4H2,(H,21,22)(H,23,24)(H2,18,19,20)(H3,12,14,15,17)/t6-,7+/m1/s1
InChI KeyCQCAEOCIDCCJDQ-RQJHMYQMSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as nucleoside and nucleotide analogues. These are analogues of nucleosides and nucleotides. These include phosphonated nucleosides, C-glycosylated nucleoside bases, analogues where the sugar unit is a pyranose, and carbocyclic nucleosides, among others.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassNucleoside and nucleotide analogues
Sub ClassNot Available
Direct ParentNucleoside and nucleotide analogues
Alternative Parents
Substituents
  • 6-oxopurine
  • Hypoxanthine
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Pyrimidone
  • Monoalkyl phosphate
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Pyrimidine
  • Alkyl phosphate
  • Imidazole
  • Heteroaromatic compound
  • Azole
  • Vinylogous amide
  • Azacycle
  • Organoheterocyclic compound
  • Amine
  • Primary amine
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Process

Naturally occurring process:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.83 g/LALOGPS
logP0ALOGPS
logP-1.8ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)0.84ChemAxon
pKa (Strongest Basic)1.72ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area245.12 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity99.32 m³·mol⁻¹ChemAxon
Polarizability38.04 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-054k-8894300000-53bc51e3a99497bf3809Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001r-2393800000-f37602c7de86b31d650cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-1290000000-fccbb1906a5586a4a9f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001j-9881000000-96a600888a7c1745af51Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0040900000-5e173b4603630bf145ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03fr-9220000000-a0c27024df7d6e4d2c5fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-9400000000-16be0451d6d2e18b72f2Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound452506
PDB IDNot Available
ChEBI ID64174
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Kewn S, Hoggard PG, Sales SD, Jones K, Maher B, Khoo SH, Back DJ: Development of enzymatic assays for quantification of intracellular lamivudine and carbovir triphosphate levels in peripheral blood mononuclear cells from human immunodeficiency virus-infected patients. Antimicrob Agents Chemother. 2002 Jan;46(1):135-43. [PubMed:11751124 ]
  2. Harris M, Back D, Kewn S, Jutha S, Marina R, Montaner JS: Intracellular carbovir triphosphate levels in patients taking abacavir once a day. AIDS. 2002 May 24;16(8):1196-7. [PubMed:12004286 ]
  3. Miller WH, Daluge SM, Garvey EP, Hopkins S, Reardon JE, Boyd FL, Miller RL: Phosphorylation of carbovir enantiomers by cellular enzymes determines the stereoselectivity of antiviral activity. J Biol Chem. 1992 Oct 15;267(29):21220-4. [PubMed:1383219 ]
  4. Cai Z, Fung EN, Sinhababu AK: Capillary electrophoresis-ion trap mass spectrometry analysis of Ziagen and its phosphorylated metabolites. Electrophoresis. 2003 Sep;24(18):3160-4. [PubMed:14518039 ]
  5. Pruvost A, Theodoro F, Agrofoglio L, Negredo E, Benech H: Specificity enhancement with LC-positive ESI-MS/MS for the measurement of nucleotides: application to the quantitative determination of carbovir triphosphate, lamivudine triphosphate and tenofovir diphosphate in human peripheral blood mononuclear cells. J Mass Spectrom. 2008 Feb;43(2):224-33. [PubMed:17935070 ]
  6. Moyle G, Boffito M, Fletcher C, Higgs C, Hay PE, Song IH, Lou Y, Yuen GJ, Min SS, Guerini EM: Steady-state pharmacokinetics of abacavir in plasma and intracellular carbovir triphosphate following administration of abacavir at 600 milligrams once daily and 300 milligrams twice daily in human immunodeficiency virus-infected subjects. Antimicrob Agents Chemother. 2009 Apr;53(4):1532-8. doi: 10.1128/AAC.01000-08. Epub 2009 Feb 2. [PubMed:19188387 ]
  7. Goicoechea M, Jain S, Bi L, Sun S, Smith G, Ha B, Richman D, Louie S, Haubrich R: Interlaboratory measurement differences in intracellular carbovir triphosphate concentrations in HIV-infected patients: sources of variability in processing, shipping, and quantitation. J Clin Pharmacol. 2010 Aug;50(8):968-74. doi: 10.1177/0091270009352186. Epub 2009 Dec 1. [PubMed:19952374 ]
  8. Jackson A, Moyle G, Dickinson L, Back D, Khoo S, Taylor J, Gedela K, Abongomera G, Gazzard B, Boffito M: Pharmacokinetics of abacavir and its anabolite carbovir triphosphate without and with darunavir/ritonavir or raltegravir in HIV-infected subjects. Antivir Ther. 2012;17(1):19-24. doi: 10.3851/IMP1910. [PubMed:22267465 ]
  9. White EL, Parker WB, Macy LJ, Shaddix SC, McCaleb G, Secrist JA 3rd, Vince R, Shannon WM: Comparison of the effect of Carbovir, AZT, and dideoxynucleoside triphosphates on the activity of human immunodeficiency virus reverse transcriptase and selected human polymerases. Biochem Biophys Res Commun. 1989 Jun 15;161(2):393-8. [PubMed:2472136 ]