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Record Information
Version3.6
Creation Date2013-07-04 18:57:46 UTC
Update Date2016-02-11 08:12:25 UTC
HMDB IDHMDB60759
Secondary Accession NumbersNone
Metabolite Identification
Common Name4-Carboxynevirapine
Description4-Carboxynevirapine is a metabolite of nevirapine. Nevirapine, also marketed under the trade name Viramune, is a non-nucleoside reverse transcriptase inhibitor (NNRTI) used to treat HIV-1 infection and AIDS. As with other antiretroviral drugs, HIV rapidly develops resistance if nevirapine is used alone, so recommended therapy consists of combinations of three or more antiretrovirals. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC15H12N4O3
Average Molecular Weight296.2808
Monoisotopic Molecular Weight296.09094027
IUPAC Name2-cyclopropyl-10-oxo-2,4,9,15-tetraazatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,11,13-hexaene-7-carboxylic acid
Traditional Name2-cyclopropyl-10-oxo-2,4,9,15-tetraazatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,11,13-hexaene-7-carboxylic acid
CAS Registry NumberNot Available
SMILES
OC(=O)C1=CC=NC2=C1NC(=O)C1=CC=CN=C1N2C1CC1
InChI Identifier
InChI=1S/C15H12N4O3/c20-14-10-2-1-6-16-12(10)19(8-3-4-8)13-11(18-14)9(15(21)22)5-7-17-13/h1-2,5-8H,3-4H2,(H,18,20)(H,21,22)
InChI KeyInChIKey=WDXCMIDQWGYHIN-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alkyldiarylamines. These are tertiary alkylarylamines having two aryl and one alkyl groups attached to the amino group.
KingdomOrganic compounds
Super ClassOrganonitrogen compounds
ClassAmines
Sub ClassTertiary amines
Direct ParentAlkyldiarylamines
Alternative Parents
Substituents
  • Alkyldiarylamine
  • Pyrido-para-diazepine
  • Pyridine carboxylic acid or derivatives
  • Pyridine carboxylic acid
  • Para-diazepine
  • Imidolactam
  • Pyridine
  • Heteroaromatic compound
  • Vinylogous amide
  • Secondary carboxylic acid amide
  • Lactam
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Membrane (predicted from logP)
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 Solubility0.52 mg/mLALOGPS
logP1.18ALOGPS
logP2.08ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)4.58ChemAxon
pKa (Strongest Basic)3.37ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area95.42 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity79.7 m3·mol-1ChemAxon
Polarizability28.86 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB LinkKEGG Link
Nevirapine Metabolism PathwaySMP00642Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00727
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB60759
Metagene LinkHMDB60759
METLIN IDNot Available
PubChem Compound10709035
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available