You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2013-07-04 18:53:52 UTC
Update Date2017-03-02 22:05:20 UTC
HMDB IDHMDB60705
Secondary Accession NumbersNone
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
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity111.84 m3·mol-1ChemAxon
Polarizability44.08 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot 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 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
      NuGOwiki LinkHMDB60705
      Metagene LinkHMDB60705
      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