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Record Information
Version4.0
Creation Date2013-07-04 18:54:58 UTC
Update Date2017-09-27 08:43:53 UTC
HMDB IDHMDB0060720
Secondary Accession Numbers
  • HMDB60720
Metabolite Identification
Common Name2-Hydroxynevirapine glucuronide
Description2-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,6S)-6-({2-cyclopropyl-10-hydroxy-7-methyl-2,4,9,15-tetraazatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-5-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6S)-6-({2-cyclopropyl-10-hydroxy-7-methyl-2,4,9,15-tetraazatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-5-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
CC1=CC(O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)=NC2=C1N=C(O)C1=C(N=CC=C1)N2C1CC1
InChI Identifier
InChI=1S/C21H22N4O8/c1-8-7-11(32-21-15(28)13(26)14(27)16(33-21)20(30)31)23-18-12(8)24-19(29)10-3-2-6-22-17(10)25(18)9-4-5-9/h2-3,6-7,9,13-16,21,26-28H,4-5H2,1H3,(H,24,29)(H,30,31)/t13-,14-,15+,16-,21+/m0/s1
InChI KeyRNMZKTLILDCQOC-KUSYAZKWSA-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
  • Hexose monosaccharide
  • Alkyldiarylamine
  • Glycosyl compound
  • O-glycosyl compound
  • Pyrido-para-diazepine
  • Beta-hydroxy acid
  • Methylpyridine
  • Hydroxy acid
  • Monosaccharide
  • Oxane
  • Pyran
  • Pyridine
  • Imidolactam
  • Cyclic carboximidic acid
  • Heteroaromatic compound
  • Secondary alcohol
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboxylic acid
  • Acetal
  • Monocarboxylic acid or derivatives
  • Polyol
  • Oxacycle
  • Organopnictogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxide
  • 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 Solubility1.39 g/LALOGPS
logP-0.08ALOGPS
logP0.43ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)2.74ChemAxon
pKa (Strongest Basic)3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area178.06 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity112.54 m³·mol⁻¹ChemAxon
Polarizability44.93 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, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052f-0040900000-ae232306a8c13f74808fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00lr-0190000000-ba33355863d8c52c3211View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-6290000000-4d608cc9ada10bbc4758View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-08fr-2340900000-1a63677f82c040cb1b8fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01su-5923500000-ace69787f4336f56caf1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001l-6390000000-406f775a2005ea731050View 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 IDDBMET00685
      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