Test Metabolite (CHEM022496)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:37:31 UTC
Update Date2016-11-09 01:17:31 UTC
Accession NumberCHEM022496
Identification
Common NameTest Metabolite
ClassSmall Molecule
DescriptionAbacavir (ABC) is a powerful nucleoside analog reverse transcriptase inhibitor (NRTI) used to treat HIV and AIDS. Chemically, it is a synthetic carbocyclic nucleoside and is the enantiomer with 1S, 4R absolute configuration on the cyclopentene ring. In vivo, Abacavir dissociates to its free base, abacavir.
Contaminant Sources
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
ABCChEBI
{(1S-cis)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]cyclopent-2-en-1-yl}methanolChEBI
(1S,4R)-4-(2-Amino-6-(cyclopropylamino)-9H-purin-9-yl)-2-cyclopentene-1-methanolHMDB
Abacavir succinateHMDB
ZiagenHMDB
Abacavir sulfateHMDB
Chemical FormulaC14H18N6O
Average Molecular Mass286.332 g/mol
Monoisotopic Mass286.154 g/mol
CAS Registry NumberNot Available
IUPAC Name[(1S,4R)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]cyclopent-2-en-1-yl]methanol
Traditional Nameabacavir
SMILESNC1=NC2=C(N=CN2[C@@H]2C[C@H](CO)C=C2)C(NC2CC2)=N1
InChI IdentifierInChI=1S/C14H18N6O/c15-14-18-12(17-9-2-3-9)11-13(19-14)20(7-16-11)10-4-1-8(5-10)6-21/h1,4,7-10,21H,2-3,5-6H2,(H3,15,17,18,19)/t8-,10+/m1/s1
InChI KeyMCGSCOLBFJQGHM-SCZZXKLOSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1,3-substituted cyclopentyl purine nucleosides. These are nucleoside analogues with a structure that consists of a cyclobutane that is substituted a the 1-position with a hydroxyl group and at the 3-position with either a purine base.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassNucleoside and nucleotide analogues
Sub ClassCyclopentyl nucleosides
Direct Parent1,3-substituted cyclopentyl purine nucleosides
Alternative Parents
Substituents
  • 1,3-substituted cyclopentyl purine nucleoside
  • 6-alkylaminopurine
  • 6-aminopurine
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Secondary aliphatic/aromatic amine
  • N-substituted imidazole
  • Pyrimidine
  • Imidolactam
  • Heteroaromatic compound
  • Azole
  • Imidazole
  • Secondary amine
  • Organoheterocyclic compound
  • Azacycle
  • Amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Primary alcohol
  • Primary amine
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.21 g/LALOGPS
logP0.61ALOGPS
logP0.39ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)15.41ChemAxon
pKa (Strongest Basic)5.77ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area101.88 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity82.62 m³·mol⁻¹ChemAxon
Polarizability30.43 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-4290000000-ff09f3896a50abd46e5cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0005-9257000000-21b4bbc1ab23c07507d6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0090000000-0946b359f044edc1eaa7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-2190000000-64675b2273332e37f39aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9410000000-d05153b2e67c168956b2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-2944c593361dbd76b614Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052r-2390000000-06a2fd880fff3ed2e268Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9630000000-7c461fd855fa0cc2d7b1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000l-0790000000-368d898ea37a7e409e6eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-fcb41525305a5be74f3aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0920000000-ce3e8f7641b332656356Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-e97d53ff96d49e16f45aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0190000000-992655fbf9c97b5fcce1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-0930000000-f24bb2b6a90e0a5559a1Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB01048
HMDB IDHMDB0015182
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAbacavir
Chemspider ID390063
ChEBI ID421707
PubChem Compound ID441300
Kegg Compound IDC07624
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Zucman D, Truchis Pd, Majerholc C, Stegman S, Caillat-Zucman S: Prospective screening for human leukocyte antigen-B*5701 avoids abacavir hypersensitivity reaction in the ethnically mixed French HIV population. J Acquir Immune Defic Syndr. 2007 May 1;45(1):1-3.
2. FDA label
3. PharmGKB: http://pharmgkb.org/pathway/PA166104634#
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=11678376
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=11806176
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=12781181
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=15887959
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=16458506
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=16539393
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=16759112
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=17172311
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=17870541
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=18029175
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=18549801
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=24751900
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=25017682
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=25674793
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=26024233