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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-04 18:53:52 UTC
Update Date2017-10-23 19:15:46 UTC
HMDB IDHMDB0060705
Secondary Accession Numbers
  • HMDB60705
Metabolite Identification
Common Name12-Hydroxynevirapine glucuronide
Description12-Hydroxynevirapine glucuronide 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 FormulaC21H22N4O8
Average Molecular Weight458.4214
Monoisotopic Molecular Weight458.1437637
IUPAC Name(2S,3S,4S,5R)-3,4,5-trihydroxy-6-{[2-(2-hydroxycyclopropyl)-7-methyl-2,4,9,15-tetraazatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,9,12,14-heptaen-10-yl]oxy}oxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R)-3,4,5-trihydroxy-6-{[2-(2-hydroxycyclopropyl)-7-methyl-2,4,9,15-tetraazatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,9,12,14-heptaen-10-yl]oxy}oxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
CC1=C2N=C(OC3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)C(O)=O)C3=C(N=CC=C3)N(C3CC3O)C2=NC=C1
InChI Identifier
InChI=1S/C21H22N4O8/c1-8-4-6-23-18-12(8)24-19(9-3-2-5-22-17(9)25(18)10-7-11(10)26)33-21-15(29)13(27)14(28)16(32-21)20(30)31/h2-6,10-11,13-16,21,26-29H,7H2,1H3,(H,30,31)/t10?,11?,13-,14-,15+,16-,21?/m0/s1
InChI KeyUVZMQJUCOZEMQZ-RDPCRGLVSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as o-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through an O-glycosidic bond.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
Direct ParentO-glucuronides
Alternative Parents
Substituents
  • 1-o-glucuronide
  • O-glucuronide
  • Alkyldiarylamine
  • Glycosyl compound
  • O-glycosyl compound
  • Pyrido-para-diazepine
  • Beta-hydroxy acid
  • Methylpyridine
  • Hydroxy acid
  • Monosaccharide
  • Oxane
  • Pyran
  • Pyridine
  • Imidolactone
  • Imidolactam
  • Heteroaromatic compound
  • Secondary alcohol
  • Cyclopropanol
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Oxacycle
  • Acetal
  • Polyol
  • Monocarboxylic acid or derivatives
  • Organopnictogen compound
  • Alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organonitrogen compound
  • Carbonyl group
  • 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 Solubility1.45 g/LALOGPS
logP-0.58ALOGPS
logP-1.6ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)2.57ChemAxon
pKa (Strongest Basic)4.61ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area178.06 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity111.84 m³·mol⁻¹ChemAxon
Polarizability44.08 ųChemAxon
Number of Rings5ChemAxon
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, Positivesplash10-054o-9316800000-d96dd4aace090a4e7ee9View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0a4r-5261049000-d43cc6f3459aa48de843View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0030900000-500d28d5628f38d3c6c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0190100000-88665b3063b67868de3bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aor-3090000000-905144dc1d7153e1ff49View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0bt9-1121900000-e12fed92493fe1b0bee6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gzj-6747900000-d15a990f677806f2cbbaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-6390000000-0152d71f8d201776e7d0View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB/PathwhizKEGG
Nevirapine Metabolism PathwayPw000618Pw000618 greyscalePw000618 simpleNot Available
Displaying 1 entry
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 IDDBMET00669
      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 CompoundNot Available
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available