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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:00:26 UTC
Update Date2020-02-26 21:39:13 UTC
HMDB IDHMDB0013912
Secondary Accession Numbers
  • HMDB13912
Metabolite Identification
Common Name2-Hydroxynevirapine
DescriptionN-Desmethylcitalopram belongs to the class of organic compounds known as phenylbutylamines. Phenylbutylamines are compounds containing a phenylbutylamine moiety, which consists of a phenyl group substituted at the fourth carbon by an butan-1-amine. N-Desmethylcitalopram is a very strong basic compound (based on its pKa). N-Desmethylcitalopram exists in all living organisms, ranging from bacteria to humans. Within humans, N-desmethylcitalopram participates in a number of enzymatic reactions. In particular, N-desmethylcitalopram can be converted into citalopram aldehyde and methylammonium; which is catalyzed by the enzymes amine oxidase [flavin-containing] a and amine oxidase [flavin-containing] b. In addition, N-desmethylcitalopram and formaldehyde can be biosynthesized from citalopram; which is mediated by the enzymes cytochrome P450 2D6, cytochrome P450 3A7, and cytochrome P450 2C19. In humans, N-desmethylcitalopram is involved in citalopram metabolism pathway. N-Desmethylcitalopram is only found in individuals that have used or taken Citalopram.
Structure
Data?1582753153
Synonyms
ValueSource
Monodesmethylcitalopram monohydrochlorideHMDB
MonodesmethylcitalopramHMDB
Monodesmethylcitalopram oxalateHMDB
Chemical FormulaC15H14N4O2
Average Molecular Weight282.2973
Monoisotopic Molecular Weight282.111675712
IUPAC Name2-cyclopropyl-5-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-5-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=C3)N(C3CC3)C2=NC(O)=C1
InChI Identifier
InChI=1S/C15H14N4O2/c1-8-7-11(20)17-14-12(8)18-15(21)10-3-2-6-16-13(10)19(14)9-4-5-9/h2-3,6-7,9H,4-5H2,1H3,(H,17,20)(H,18,21)
InChI KeyLFZSOJABLBVGRJ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylbutylamines. Phenylbutylamines are compounds containing a phenylbutylamine moiety, which consists of a phenyl group substituted at the fourth carbon by an butan-1-amine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylbutylamines
Direct ParentPhenylbutylamines
Alternative Parents
Substituents
  • Phenylbutylamine
  • Isocoumaran
  • Fluorobenzene
  • Halobenzene
  • Aralkylamine
  • Aryl fluoride
  • Aryl halide
  • Dialkyl ether
  • Secondary aliphatic amine
  • Ether
  • Carbonitrile
  • Nitrile
  • Oxacycle
  • Secondary amine
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Amine
  • Organohalogen compound
  • Organofluoride
  • Organonitrogen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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 Solubility0.45 g/LALOGPS
logP1.68ALOGPS
logP2.78ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)10.27ChemAxon
pKa (Strongest Basic)3.44ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area78.35 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity79.78 m³·mol⁻¹ChemAxon
Polarizability28.83 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]+163.14531661259
DarkChem[M-H]-160.55531661259
DeepCCS[M+H]+176.51130932474
DeepCCS[M-H]-174.15330932474
DeepCCS[M-2H]-207.40430932474
DeepCCS[M+Na]+182.6330932474
AllCCS[M+H]+165.632859911
AllCCS[M+H-H2O]+162.132859911
AllCCS[M+NH4]+168.932859911
AllCCS[M+Na]+169.832859911
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
2-HydroxynevirapineCC1=C2NC(=O)C3=C(N=CC=C3)N(C3CC3)C2=NC(O)=C13794.4Standard polar33892256
2-HydroxynevirapineCC1=C2NC(=O)C3=C(N=CC=C3)N(C3CC3)C2=NC(O)=C12727.7Standard non polar33892256
2-HydroxynevirapineCC1=C2NC(=O)C3=C(N=CC=C3)N(C3CC3)C2=NC(O)=C12511.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Hydroxynevirapine,1TMS,isomer #1CC1=CC(O[Si](C)(C)C)=NC2=C1NC(=O)C1=CC=CN=C1N2C1CC12791.1Semi standard non polar33892256
2-Hydroxynevirapine,1TMS,isomer #2CC1=CC(O)=NC2=C1N([Si](C)(C)C)C(=O)C1=CC=CN=C1N2C1CC12554.3Semi standard non polar33892256
2-Hydroxynevirapine,2TMS,isomer #1CC1=CC(O[Si](C)(C)C)=NC2=C1N([Si](C)(C)C)C(=O)C1=CC=CN=C1N2C1CC12576.1Semi standard non polar33892256
2-Hydroxynevirapine,2TMS,isomer #1CC1=CC(O[Si](C)(C)C)=NC2=C1N([Si](C)(C)C)C(=O)C1=CC=CN=C1N2C1CC12646.0Standard non polar33892256
2-Hydroxynevirapine,2TMS,isomer #1CC1=CC(O[Si](C)(C)C)=NC2=C1N([Si](C)(C)C)C(=O)C1=CC=CN=C1N2C1CC13544.6Standard polar33892256
2-Hydroxynevirapine,1TBDMS,isomer #1CC1=CC(O[Si](C)(C)C(C)(C)C)=NC2=C1NC(=O)C1=CC=CN=C1N2C1CC12976.8Semi standard non polar33892256
2-Hydroxynevirapine,1TBDMS,isomer #2CC1=CC(O)=NC2=C1N([Si](C)(C)C(C)(C)C)C(=O)C1=CC=CN=C1N2C1CC12812.7Semi standard non polar33892256
2-Hydroxynevirapine,2TBDMS,isomer #1CC1=CC(O[Si](C)(C)C(C)(C)C)=NC2=C1N([Si](C)(C)C(C)(C)C)C(=O)C1=CC=CN=C1N2C1CC12945.0Semi standard non polar33892256
2-Hydroxynevirapine,2TBDMS,isomer #1CC1=CC(O[Si](C)(C)C(C)(C)C)=NC2=C1N([Si](C)(C)C(C)(C)C)C(=O)C1=CC=CN=C1N2C1CC13046.6Standard non polar33892256
2-Hydroxynevirapine,2TBDMS,isomer #1CC1=CC(O[Si](C)(C)C(C)(C)C)=NC2=C1N([Si](C)(C)C(C)(C)C)C(=O)C1=CC=CN=C1N2C1CC13628.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxynevirapine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0gyx-1890000000-d6054af1eebe72c5c4b62017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxynevirapine GC-MS (1 TMS) - 70eV, Positivesplash10-001i-4798000000-b8c5512169e5a41410d82017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxynevirapine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-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 - 2-Hydroxynevirapine 10V, Positive-QTOFsplash10-001i-0090000000-ce583e2d4d570a450bca2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxynevirapine 20V, Positive-QTOFsplash10-00lr-1090000000-e083894c3878d5c742162016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxynevirapine 40V, Positive-QTOFsplash10-0udl-9060000000-54c0ec5ecb9c00e9cbd72016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxynevirapine 10V, Negative-QTOFsplash10-001i-0090000000-d505115f37815beecdcc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxynevirapine 20V, Negative-QTOFsplash10-001l-0090000000-a4df3e2565cf4bfd0f372016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxynevirapine 40V, Negative-QTOFsplash10-0fkd-1390000000-75ca606ca619a020a8d52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxynevirapine 10V, Negative-QTOFsplash10-001i-0090000000-d72761c0346bc09759b02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxynevirapine 20V, Negative-QTOFsplash10-001i-0090000000-adc3593c967ca78592922021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxynevirapine 40V, Negative-QTOFsplash10-03ml-1690000000-9ef93e955157aa2c14c72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxynevirapine 10V, Positive-QTOFsplash10-001i-0090000000-7c900f9f8b3f179143932021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxynevirapine 20V, Positive-QTOFsplash10-001l-0090000000-c910612007c88e00763a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxynevirapine 40V, Positive-QTOFsplash10-004l-0390000000-09499c647b8bf959668a2021-09-25Wishart 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 ID142424
KEGG Compound IDC16608
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDesmethylcitalopram
METLIN IDNot Available
PubChem Compound162180
PDB IDNot Available
ChEBI ID586865
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