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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-04 18:57:46 UTC
Update Date2017-12-07 17:55:23 UTC
HMDB IDHMDB0060759
Secondary Accession Numbers
  • HMDB60759
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 KeyWDXCMIDQWGYHIN-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as alkyldiarylamines. These are tertiary alkylarylamines having two aryl and one alkyl groups attached to the amino group.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic nitrogen compounds
Sub ClassOrganonitrogen compounds
Direct ParentAlkyldiarylamines
Alternative Parents
Substituents
  • Alkyldiarylamine
  • Pyrido-para-diazepine
  • Pyridine carboxylic acid
  • Pyridine carboxylic acid or derivatives
  • Para-diazepine
  • Pyridine
  • Imidolactam
  • Heteroaromatic compound
  • Vinylogous amide
  • Carboxamide group
  • Lactam
  • Secondary carboxylic acid amide
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Biological role:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity79.7 m³·mol⁻¹ChemAxon
Polarizability28.86 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kuu-0490000000-868c3fa487d18d561bcfView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fn9-8497000000-b1059cc66c8651a2f9f6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-03fc360d0dd52eeaf3ebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ufs-0090000000-b9d8e1529284c8d08e6aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gvx-8190000000-8eeb53c98632b1d30dadView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udj-0090000000-3758c78030929ebc316cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090000000-b0d5580a8d1a49c7fa29View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bt9-0490000000-e08953300981317eca97View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB/PathwhizKEGG
Nevirapine Metabolism PathwayPw000618Pw000618 greyscalePw000618 simpleNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      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
      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