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 Date2013-07-22 19:49:49 UTC
Update Date2016-02-11 08:18:56 UTC
HMDB IDHMDB61130
Secondary Accession NumbersNone
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=1/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+/s2
InChI KeyInChIKey=IVZWGLRSSHUFTI-YOYHKZRZNA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as o-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through an O-glycosidic bond.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassSugar acids and derivatives
Direct ParentO-glucuronides
Alternative Parents
Substituents
  • O-glucuronide
  • 1-o-glucuronide
  • Alkyldiarylamine
  • Pyrido-para-diazepine
  • O-glycosyl compound
  • Glycosyl compound
  • Pyran carboxylic acid
  • Pyran carboxylic acid or derivatives
  • Methylpyridine
  • Beta-hydroxy acid
  • Para-diazepine
  • Imidolactam
  • Pyridine
  • Pyran
  • Oxane
  • Monosaccharide
  • Hydroxy acid
  • Heteroaromatic compound
  • Vinylogous amide
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Polyol
  • Lactam
  • Carboxamide group
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Acetal
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • 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 Solubility3.74 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity111.47 m3·mol-1ChemAxon
Polarizability44.55 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 QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
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
NuGOwiki LinkHMDB61130
Metagene LinkHMDB61130
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