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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:36 UTC
HMDB IDHMDB0014383
Secondary Accession Numbers
  • HMDB14383
Metabolite Identification
Common NameNevirapine
DescriptionNevirapine is only found in individuals that have used or taken this drug. It is a potent, non-nucleoside reverse transcriptase inhibitor used in combination with nucleoside analogues for treatment of HIV infection and AIDS. [PubChem]Nevirapine binds directly to reverse transcriptase (RT) and blocks the RNA-dependent and DNA-dependent DNA polymerase activities by causing a disruption of the enzyme's catalytic site. The activity of nevirapine does not compete with template or nucleoside triphosphates.
Structure
Data?1582753172
Synonyms
ValueSource
11-Cyclopropyl-5,11-dihydro-4-methyl-6H-dipyrido(3,2-b:2',3'-e)(1,4)diazepin-6-oneChEBI
NEVChEBI
NVPChEBI
ViramuneChEBI
ABBR NVPKegg
Nevirapine hemihydrateHMDB
BI RG 587HMDB
BIRG587HMDB
Hemihydrate, nevirapineHMDB
BI-RG-587HMDB
Chemical FormulaC15H14N4O
Average Molecular Weight266.2979
Monoisotopic Molecular Weight266.11676109
IUPAC Name2-cyclopropyl-7-methyl-2,4,9,15-tetraazatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,12,14-hexaen-10-one
Traditional Namenevirapine
CAS Registry Number129618-40-2
SMILES
CC1=C2NC(=O)C3=C(N=CC=C3)N(C3CC3)C2=NC=C1
InChI Identifier
InChI=1S/C15H14N4O/c1-9-6-8-17-14-12(9)18-15(20)11-3-2-7-16-13(11)19(14)10-4-5-10/h2-3,6-8,10H,4-5H2,1H3,(H,18,20)
InChI KeyNQDJXKOVJZTUJA-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
  • 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 Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point196.06 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.1 g/LNot Available
LogP2.5Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.1 g/LALOGPS
logP1.75ALOGPS
logP2.49ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)10.37ChemAxon
pKa (Strongest Basic)5.06ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area58.12 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity77.48 m³·mol⁻¹ChemAxon
Polarizability27.8 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]+161.83231661259
DarkChem[M-H]-161.70831661259
DeepCCS[M+H]+170.63730932474
DeepCCS[M-H]-168.27930932474
DeepCCS[M-2H]-201.4730932474
DeepCCS[M+Na]+176.73130932474
AllCCS[M+H]+162.132859911
AllCCS[M+H-H2O]+158.432859911
AllCCS[M+NH4]+165.532859911
AllCCS[M+Na]+166.532859911
AllCCS[M-H]-164.632859911
AllCCS[M+Na-2H]-163.932859911
AllCCS[M+HCOO]-163.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
NevirapineCC1=C2NC(=O)C3=C(N=CC=C3)N(C3CC3)C2=NC=C13510.5Standard polar33892256
NevirapineCC1=C2NC(=O)C3=C(N=CC=C3)N(C3CC3)C2=NC=C12403.5Standard non polar33892256
NevirapineCC1=C2NC(=O)C3=C(N=CC=C3)N(C3CC3)C2=NC=C12298.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Nevirapine,1TMS,isomer #1CC1=CC=NC2=C1N([Si](C)(C)C)C(=O)C1=CC=CN=C1N2C1CC12390.5Semi standard non polar33892256
Nevirapine,1TMS,isomer #1CC1=CC=NC2=C1N([Si](C)(C)C)C(=O)C1=CC=CN=C1N2C1CC12391.7Standard non polar33892256
Nevirapine,1TMS,isomer #1CC1=CC=NC2=C1N([Si](C)(C)C)C(=O)C1=CC=CN=C1N2C1CC13572.1Standard polar33892256
Nevirapine,1TBDMS,isomer #1CC1=CC=NC2=C1N([Si](C)(C)C(C)(C)C)C(=O)C1=CC=CN=C1N2C1CC12630.9Semi standard non polar33892256
Nevirapine,1TBDMS,isomer #1CC1=CC=NC2=C1N([Si](C)(C)C(C)(C)C)C(=O)C1=CC=CN=C1N2C1CC12594.6Standard non polar33892256
Nevirapine,1TBDMS,isomer #1CC1=CC=NC2=C1N([Si](C)(C)C(C)(C)C)C(=O)C1=CC=CN=C1N2C1CC13625.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Nevirapine GC-MS (Non-derivatized) - 70eV, Positivesplash10-01s9-0890000000-c2ef64541073a1c774c32017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Nevirapine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Nevirapine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Nevirapine , positive-QTOFsplash10-016r-1390000000-cbb2d729a2b310bf5dd02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nevirapine , positive-QTOFsplash10-016r-0290000000-64af72aec31bfd168e682017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nevirapine , positive-QTOFsplash10-004i-3980000000-98e328d2867c437169732017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nevirapine 35V, Positive-QTOFsplash10-00or-0390000000-8627dbd7619ad65895662021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nevirapine 10V, Positive-QTOFsplash10-014i-0090000000-e341212035575baee47c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nevirapine 20V, Positive-QTOFsplash10-014i-1090000000-aa8be82ca660a3a1654d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nevirapine 40V, Positive-QTOFsplash10-0k96-9240000000-96f26abab0ca2960a8d92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nevirapine 10V, Negative-QTOFsplash10-014i-0090000000-5ff2e0be399277e2d1e42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nevirapine 20V, Negative-QTOFsplash10-016r-0090000000-e6562b6940dd28d0a37b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nevirapine 40V, Negative-QTOFsplash10-0a6r-1890000000-d60a9db4a4fef99e1ca52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nevirapine 10V, Positive-QTOFsplash10-014i-0090000000-d1a08ff6bcda467abc312021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nevirapine 20V, Positive-QTOFsplash10-016r-0090000000-ab3762b78a7dc338267f2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nevirapine 40V, Positive-QTOFsplash10-004i-0390000000-40b55ad31c970d6bd2e32021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nevirapine 10V, Negative-QTOFsplash10-014i-0090000000-b7ee7f3fd2558633e8402021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nevirapine 20V, Negative-QTOFsplash10-014i-0090000000-b8840f336feb8c33bccc2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nevirapine 40V, Negative-QTOFsplash10-0092-2950000000-37fa8e70d7fa15c734392021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00238 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00238 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00238
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4308
KEGG Compound IDC07263
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNevirapine
METLIN IDNot Available
PubChem Compound4463
PDB IDNVP
ChEBI ID63613
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 References
  1. (). FDA label . .