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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:00:26 UTC
Update Date2020-02-26 21:39:14 UTC
HMDB IDHMDB0013913
Secondary Accession Numbers
  • HMDB13913
Metabolite Identification
Common Name8-Hydroxynevirapine
Description8-Hydroxynevirapine belongs to the class of organic compounds known as alkyldiarylamines. These are tertiary alkylarylamines having two aryl and one alkyl groups attached to the amino group. 8-Hydroxynevirapine is a very strong basic compound (based on its pKa). Within humans, 8-hydroxynevirapine participates in a number of enzymatic reactions. In particular, 8-hydroxynevirapine can be biosynthesized from nevirapine; which is catalyzed by the enzymes cytochrome P450 3A4, cytochrome P450 2B6, and cytochrome P450 2D6. In addition, 8-hydroxynevirapine and uridine diphosphate glucuronic acid can be converted into 8-hydroxynevirapine glucuronide and uridine 5'-diphosphate; which is catalyzed by the enzyme UDP-glucuronosyltransferase 1-10. In humans, 8-hydroxynevirapine is involved in nevirapine metabolism pathway. These are organic compounds containing 1,4-diazepine, a seven-member heterocyclic ring with two nitrogen atoms in positions 1 and 4. 8-Hydroxynevirapine is a metabolite of Nevirapine. 8-Hydroxynevirapine is only found in individuals that have used or taken Nevirapine.
Structure
Data?1582753153
SynonymsNot Available
Chemical FormulaC15H14N4O2
Average Molecular Weight282.2973
Monoisotopic Molecular Weight282.111675712
IUPAC Name2-cyclopropyl-13-hydroxy-7-methyl-2,4,9,15-tetraazatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,12,14-hexaen-10-one
Traditional Name2-cyclopropyl-13-hydroxy-7-methyl-2,4,9,15-tetraazatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,12,14-hexaen-10-one
CAS Registry NumberNot Available
SMILES
CC1=C2NC(=O)C3=C(N=CC(O)=C3)N(C3CC3)C2=NC=C1
InChI Identifier
InChI=1S/C15H14N4O2/c1-8-4-5-16-14-12(8)18-15(21)11-6-10(20)7-17-13(11)19(14)9-2-3-9/h4-7,9,20H,2-3H2,1H3,(H,18,21)
InChI KeyDZPVEPLRIKDBFC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alkyldiarylamines. These are tertiary alkylarylamines having two aryl and one alkyl groups attached to the amino group.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct ParentAlkyldiarylamines
Alternative Parents
Substituents
  • Alkyldiarylamine
  • Pyrido-para-diazepine
  • Para-diazepine
  • Methylpyridine
  • Hydroxypyridine
  • Imidolactam
  • Pyridine
  • Heteroaromatic compound
  • Vinylogous amide
  • Carboxamide group
  • Lactam
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Azacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.4 g/LALOGPS
logP1.2ALOGPS
logP2.18ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)8.88ChemAxon
pKa (Strongest Basic)5.06ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area78.35 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity79.46 m³·mol⁻¹ChemAxon
Polarizability28.87 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+164.0531661259
DarkChem[M-H]-162.44831661259
DeepCCS[M+H]+171.48630932474
DeepCCS[M-H]-169.12830932474
DeepCCS[M-2H]-202.97230932474
DeepCCS[M+Na]+178.19930932474
AllCCS[M+H]+165.732859911
AllCCS[M+H-H2O]+162.232859911
AllCCS[M+NH4]+168.932859911
AllCCS[M+Na]+169.932859911
AllCCS[M-H]-167.432859911
AllCCS[M+Na-2H]-166.732859911
AllCCS[M+HCOO]-166.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
8-HydroxynevirapineCC1=C2NC(=O)C3=C(N=CC(O)=C3)N(C3CC3)C2=NC=C13722.3Standard polar33892256
8-HydroxynevirapineCC1=C2NC(=O)C3=C(N=CC(O)=C3)N(C3CC3)C2=NC=C12640.4Standard non polar33892256
8-HydroxynevirapineCC1=C2NC(=O)C3=C(N=CC(O)=C3)N(C3CC3)C2=NC=C12577.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
8-Hydroxynevirapine,1TMS,isomer #1CC1=CC=NC2=C1NC(=O)C1=CC(O[Si](C)(C)C)=CN=C1N2C1CC12818.2Semi standard non polar33892256
8-Hydroxynevirapine,1TMS,isomer #2CC1=CC=NC2=C1N([Si](C)(C)C)C(=O)C1=CC(O)=CN=C1N2C1CC12616.6Semi standard non polar33892256
8-Hydroxynevirapine,2TMS,isomer #1CC1=CC=NC2=C1N([Si](C)(C)C)C(=O)C1=CC(O[Si](C)(C)C)=CN=C1N2C1CC12579.8Semi standard non polar33892256
8-Hydroxynevirapine,2TMS,isomer #1CC1=CC=NC2=C1N([Si](C)(C)C)C(=O)C1=CC(O[Si](C)(C)C)=CN=C1N2C1CC12695.7Standard non polar33892256
8-Hydroxynevirapine,2TMS,isomer #1CC1=CC=NC2=C1N([Si](C)(C)C)C(=O)C1=CC(O[Si](C)(C)C)=CN=C1N2C1CC13650.5Standard polar33892256
8-Hydroxynevirapine,1TBDMS,isomer #1CC1=CC=NC2=C1NC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=CN=C1N2C1CC13016.8Semi standard non polar33892256
8-Hydroxynevirapine,1TBDMS,isomer #2CC1=CC=NC2=C1N([Si](C)(C)C(C)(C)C)C(=O)C1=CC(O)=CN=C1N2C1CC12864.1Semi standard non polar33892256
8-Hydroxynevirapine,2TBDMS,isomer #1CC1=CC=NC2=C1N([Si](C)(C)C(C)(C)C)C(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=CN=C1N2C1CC12967.0Semi standard non polar33892256
8-Hydroxynevirapine,2TBDMS,isomer #1CC1=CC=NC2=C1N([Si](C)(C)C(C)(C)C)C(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=CN=C1N2C1CC13087.7Standard non polar33892256
8-Hydroxynevirapine,2TBDMS,isomer #1CC1=CC=NC2=C1N([Si](C)(C)C(C)(C)C)C(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=CN=C1N2C1CC13713.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 8-Hydroxynevirapine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0gyd-1890000000-3cfd1974629bed42b7672017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Hydroxynevirapine GC-MS (1 TMS) - 70eV, Positivesplash10-002k-4869000000-743bd151da9f4be4e4222017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Hydroxynevirapine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Hydroxynevirapine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxynevirapine 10V, Positive-QTOFsplash10-001i-0090000000-4db90e3c8eec102dc1522016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxynevirapine 20V, Positive-QTOFsplash10-001i-1090000000-6ea3809a97c81c186d3b2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxynevirapine 40V, Positive-QTOFsplash10-002f-9170000000-3221a4376c5aba7ebc602016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxynevirapine 10V, Negative-QTOFsplash10-001i-0090000000-083099581e2882f2398a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxynevirapine 20V, Negative-QTOFsplash10-001l-0090000000-84dc076d6a97aa601ae12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxynevirapine 40V, Negative-QTOFsplash10-05bg-1490000000-58b85aee49066a9e29e22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxynevirapine 10V, Negative-QTOFsplash10-001i-0090000000-d72761c0346bc09759b02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxynevirapine 20V, Negative-QTOFsplash10-001i-0090000000-4b8c21e2532f349187022021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxynevirapine 40V, Negative-QTOFsplash10-03di-1490000000-e98fafeba7360778c6782021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxynevirapine 10V, Positive-QTOFsplash10-001i-0090000000-7c900f9f8b3f179143932021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxynevirapine 20V, Positive-QTOFsplash10-001l-0090000000-f426dd3b9af984da00782021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxynevirapine 40V, Positive-QTOFsplash10-004i-0190000000-ab9dbb520cbde3aefc952021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID8930647
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10755325
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available