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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-04 19:00:30 UTC
Update Date2019-07-23 07:15:07 UTC
HMDB IDHMDB0060803
Secondary Accession Numbers
  • HMDB60803
Metabolite Identification
Common Name8-Hydroxydesmethylclomipramine
Description(2S,3S,4S,5R,6S)-6-({14-chloro-2-[3-(dimethylamino)propyl]-6-hydroxy-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,12,14-hexaen-7-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid belongs to the class of organic compounds known as benzazepines. These are organic compounds containing a benzene ring fused to an azepine ring (unsaturated seven-membered heterocycle with one nitrogen atom replacing a carbon atom) (2S,3S,4S,5R,6S)-6-({14-chloro-2-[3-(dimethylamino)propyl]-6-hydroxy-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,12,14-hexaen-7-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid is a very strong basic compound (based on its pKa).
Structure
Data?1563866107
Synonyms
ValueSource
(2S,3S,4S,5R,6S)-6-({14-chloro-2-[3-(dimethylamino)propyl]-6-hydroxy-2-azatricyclo[9.4.0.0,]pentadeca-1(11),3(8),4,6,12,14-hexaen-7-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylateGenerator
Chemical FormulaC18H21ClN2O
Average Molecular Weight316.825
Monoisotopic Molecular Weight316.134241011
IUPAC Name14-chloro-2-[3-(methylamino)propyl]-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-6-ol
Traditional Name14-chloro-2-[3-(methylamino)propyl]-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-6-ol
CAS Registry NumberNot Available
SMILES
CNCCCN1C2=CC=C(O)C=C2CCC2=CC=C(Cl)C=C12
InChI Identifier
InChI=1S/C18H21ClN2O/c1-20-9-2-10-21-17-8-7-16(22)11-14(17)4-3-13-5-6-15(19)12-18(13)21/h5-8,11-12,20,22H,2-4,9-10H2,1H3
InChI KeyMRLCQGACIDFFSH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzazepines. These are organic compounds containing a benzene ring fused to an azepine ring (unsaturated seven-membered heterocycle with one nitrogen atom replacing a carbon atom).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzazepines
Sub ClassNot Available
Direct ParentBenzazepines
Alternative Parents
Substituents
  • Benzazepine
  • Tertiary aliphatic/aromatic amine
  • Dialkylarylamine
  • Azepine
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Benzenoid
  • Tertiary amine
  • Secondary aliphatic amine
  • Secondary amine
  • Vinyl chloride
  • Vinyl halide
  • Azacycle
  • Chloroalkene
  • Haloalkene
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Amine
  • Organohalogen compound
  • Organochloride
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
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 Solubility0.041 g/LALOGPS
logP3.88ALOGPS
logP3.78ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)10.63ChemAxon
pKa (Strongest Basic)9.9ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area35.5 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity92.1 m³·mol⁻¹ChemAxon
Polarizability35.16 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-203.88330932474
DeepCCS[M+Na]+179.44830932474
AllCCS[M+H]+174.132859911
AllCCS[M+H-H2O]+170.832859911
AllCCS[M+NH4]+177.232859911
AllCCS[M+Na]+178.132859911
AllCCS[M-H]-179.032859911
AllCCS[M+Na-2H]-178.832859911
AllCCS[M+HCOO]-178.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
8-HydroxydesmethylclomipramineCNCCCN1C2=CC=C(O)C=C2CCC2=CC=C(Cl)C=C123980.1Standard polar33892256
8-HydroxydesmethylclomipramineCNCCCN1C2=CC=C(O)C=C2CCC2=CC=C(Cl)C=C122786.0Standard non polar33892256
8-HydroxydesmethylclomipramineCNCCCN1C2=CC=C(O)C=C2CCC2=CC=C(Cl)C=C122788.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
8-Hydroxydesmethylclomipramine,1TMS,isomer #1CNCCCN1C2=CC=C(O[Si](C)(C)C)C=C2CCC2=CC=C(Cl)C=C212701.9Semi standard non polar33892256
8-Hydroxydesmethylclomipramine,1TMS,isomer #2CN(CCCN1C2=CC=C(O)C=C2CCC2=CC=C(Cl)C=C21)[Si](C)(C)C2948.4Semi standard non polar33892256
8-Hydroxydesmethylclomipramine,2TMS,isomer #1CN(CCCN1C2=CC=C(O[Si](C)(C)C)C=C2CCC2=CC=C(Cl)C=C21)[Si](C)(C)C2852.7Semi standard non polar33892256
8-Hydroxydesmethylclomipramine,2TMS,isomer #1CN(CCCN1C2=CC=C(O[Si](C)(C)C)C=C2CCC2=CC=C(Cl)C=C21)[Si](C)(C)C2979.8Standard non polar33892256
8-Hydroxydesmethylclomipramine,2TMS,isomer #1CN(CCCN1C2=CC=C(O[Si](C)(C)C)C=C2CCC2=CC=C(Cl)C=C21)[Si](C)(C)C3316.7Standard polar33892256
8-Hydroxydesmethylclomipramine,1TBDMS,isomer #1CNCCCN1C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2CCC2=CC=C(Cl)C=C212905.6Semi standard non polar33892256
8-Hydroxydesmethylclomipramine,1TBDMS,isomer #2CN(CCCN1C2=CC=C(O)C=C2CCC2=CC=C(Cl)C=C21)[Si](C)(C)C(C)(C)C3154.4Semi standard non polar33892256
8-Hydroxydesmethylclomipramine,2TBDMS,isomer #1CN(CCCN1C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2CCC2=CC=C(Cl)C=C21)[Si](C)(C)C(C)(C)C3279.9Semi standard non polar33892256
8-Hydroxydesmethylclomipramine,2TBDMS,isomer #1CN(CCCN1C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2CCC2=CC=C(Cl)C=C21)[Si](C)(C)C(C)(C)C3491.0Standard non polar33892256
8-Hydroxydesmethylclomipramine,2TBDMS,isomer #1CN(CCCN1C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2CCC2=CC=C(Cl)C=C21)[Si](C)(C)C(C)(C)C3488.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 8-Hydroxydesmethylclomipramine GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-7090000000-4b1a3d56016fa5618f9b2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Hydroxydesmethylclomipramine GC-MS (1 TMS) - 70eV, Positivesplash10-006x-9006000000-173771675d64f59fa4a72017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Hydroxydesmethylclomipramine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Hydroxydesmethylclomipramine 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-Hydroxydesmethylclomipramine 10V, Positive-QTOFsplash10-014r-1049000000-f70a869828ef28c08a152017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxydesmethylclomipramine 20V, Positive-QTOFsplash10-00rl-6093000000-41eb3f645b893ebed6262017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxydesmethylclomipramine 40V, Positive-QTOFsplash10-0006-9150000000-7e44a16a91368607b8482017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxydesmethylclomipramine 10V, Negative-QTOFsplash10-014i-0009000000-1f984de31886b39a29fd2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxydesmethylclomipramine 20V, Negative-QTOFsplash10-014l-1079000000-f55bbf2457fa321e42812017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxydesmethylclomipramine 40V, Negative-QTOFsplash10-05mo-2090000000-e8a8147accd3df890ae52017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxydesmethylclomipramine 10V, Positive-QTOFsplash10-00di-9003000000-34df45c4708af600dea72021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxydesmethylclomipramine 20V, Positive-QTOFsplash10-00dl-9010000000-2d144cfd68b2b1271fd72021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxydesmethylclomipramine 40V, Positive-QTOFsplash10-0596-9010000000-05b3a9ffb8e7186c35802021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxydesmethylclomipramine 10V, Negative-QTOFsplash10-014i-0049000000-ba57917986af041370042021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxydesmethylclomipramine 20V, Negative-QTOFsplash10-014l-1097000000-c33567b6ece7e293b3532021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxydesmethylclomipramine 40V, Negative-QTOFsplash10-000x-6090000000-d25fa0f33efdafe1023c2021-10-12Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
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