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Record Information
Version4.0
Creation Date2013-07-22 19:49:49 UTC
Update Date2017-10-23 19:15:53 UTC
HMDB IDHMDB0061130
Secondary Accession Numbers
  • HMDB61130
Metabolite Identification
Common Name8-Hydroxynevirapine glucuronide
Description8-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(2R,3R,4R,5S,6R)-6-({2-cyclopropyl-7-methyl-10-oxo-2,4,9,15-tetraazatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,12,14-hexaen-13-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name(2R,3R,4R,5S,6R)-6-({2-cyclopropyl-7-methyl-10-oxo-2,4,9,15-tetraazatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,12,14-hexaen-13-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
CC1=CC=NC2=C1NC(=O)C1=C(N=CC(O[C@H]3O[C@H]([C@H](O)[C@@H](O)[C@@H]3O)C(O)=O)=C1)N2C1CC1
InChI Identifier
InChI=1S/C21H22N4O8/c1-8-4-5-22-18-12(8)24-19(29)11-6-10(7-23-17(11)25(18)9-2-3-9)32-21-15(28)13(26)14(27)16(33-21)20(30)31/h4-7,9,13-16,21,26-28H,2-3H2,1H3,(H,24,29)(H,30,31)/t13-,14-,15+,16-,21+/m1/s1
InChI KeyIVZWGLRSSHUFTI-WCYOCWRHSA-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
  • Para-diazepine
  • Beta-hydroxy acid
  • Methylpyridine
  • Hydroxy acid
  • Monosaccharide
  • Oxane
  • Pyran
  • Pyridine
  • Imidolactam
  • Vinylogous amide
  • Heteroaromatic compound
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Lactam
  • Carboxamide group
  • Polyol
  • Azacycle
  • Oxacycle
  • Acetal
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Alcohol
  • 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 Solubility3.74 g/LALOGPS
logP-0.1ALOGPS
logP-1.4ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)2.93ChemAxon
pKa (Strongest Basic)5.06ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area174.57 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity111.47 m³·mol⁻¹ChemAxon
Polarizability44.55 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-9118400000-a7a05c6f368a05bcc1a5View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0a4i-4701139000-644ea49eb1d875f7ac7cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05o3-0090600000-4b470bd74c1897d1be88View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0159-0090000000-1bbb0d8feb9db6b86895View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00l6-4390000000-dccc34373a73b424ac72View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0bu0-2270900000-082906c44d4658ff7443View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1291300000-411202794ed528c9222eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-2390000000-27c8ea77e71c8756aa5bView 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 IDDBMET00779
      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