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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-04 19:03:29 UTC
Update Date2021-09-14 15:45:14 UTC
HMDB IDHMDB0060852
Secondary Accession Numbers
  • HMDB60852
Metabolite Identification
Common NameN,O-Didesmethylvenlafaxine
DescriptionN,O-Didesmethylvenlafaxine, also known as N,O-didesvenlafaxine, belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring. N,O-Didesmethylvenlafaxine is a very strong basic compound (based on its pKa). Within humans, N,O-didesmethylvenlafaxine participates in a number of enzymatic reactions. In particular, N,O-didesmethylvenlafaxine and formaldehyde can be biosynthesized from O-desmethylvenlafaxine; which is catalyzed by the enzymes cytochrome P450 3A4 and cytochrome P450 2C19. In addition, N,O-didesmethylvenlafaxine and formaldehyde can be biosynthesized from N-desmethylvenlafaxine through its interaction with the enzymes cytochrome P450 2C19 and cytochrome P450 2D6. In humans, N,O-didesmethylvenlafaxine is involved in venlafaxine metabolism pathway. It works by blocking the transporter reuptake proteins for key neurotransmitters affecting mood, thereby leaving more active neurotransmitters in the synapse.
Structure
Data?1563866113
Synonyms
ValueSource
N-DesmethyldesvenlafaxineChEBI
4-[1-(1-Hydroxycyclohexyl)-2-(methylamino)ethyl]phenolHMDB
N,O-DidesvenlafaxineHMDB
N,O-DidesmethylvenlafaxineHMDB
Chemical FormulaC15H23NO2
Average Molecular Weight249.3486
Monoisotopic Molecular Weight249.172878985
IUPAC Name4-[1-(1-hydroxycyclohexyl)-2-(methylamino)ethyl]phenol
Traditional Name4-[1-(1-hydroxycyclohexyl)-2-(methylamino)ethyl]phenol
CAS Registry Number135308-74-6
SMILES
CNCC(C1=CC=C(O)C=C1)C1(O)CCCCC1
InChI Identifier
InChI=1S/C15H23NO2/c1-16-11-14(12-5-7-13(17)8-6-12)15(18)9-3-2-4-10-15/h5-8,14,16-18H,2-4,9-11H2,1H3
InChI KeyMMSWXJSQCAEDLK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentCyclohexanols
Alternative Parents
Substituents
  • Cyclohexanol
  • Phenol
  • Aralkylamine
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Tertiary alcohol
  • 1,3-aminoalcohol
  • Cyclic alcohol
  • Secondary amine
  • Secondary aliphatic amine
  • Amine
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic nitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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 Solubility0.3 g/LALOGPS
logP2.08ALOGPS
logP1.74ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)10.29ChemAxon
pKa (Strongest Basic)9.57ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area52.49 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity73.25 m³·mol⁻¹ChemAxon
Polarizability28.62 ųChemAxon
Number of Rings2ChemAxon
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]+160.16731661259
DarkChem[M-H]-158.3931661259
DeepCCS[M+H]+161.76330932474
DeepCCS[M-H]-159.40530932474
DeepCCS[M-2H]-192.31730932474
DeepCCS[M+Na]+167.85630932474
AllCCS[M+H]+160.032859911
AllCCS[M+H-H2O]+156.332859911
AllCCS[M+NH4]+163.532859911
AllCCS[M+Na]+164.532859911
AllCCS[M-H]-164.932859911
AllCCS[M+Na-2H]-165.232859911
AllCCS[M+HCOO]-165.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N,O-DidesmethylvenlafaxineCNCC(C1=CC=C(O)C=C1)C1(O)CCCCC12566.5Standard polar33892256
N,O-DidesmethylvenlafaxineCNCC(C1=CC=C(O)C=C1)C1(O)CCCCC12144.5Standard non polar33892256
N,O-DidesmethylvenlafaxineCNCC(C1=CC=C(O)C=C1)C1(O)CCCCC12161.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N,O-Didesmethylvenlafaxine,1TMS,isomer #1CNCC(C1=CC=C(O[Si](C)(C)C)C=C1)C1(O)CCCCC12195.3Semi standard non polar33892256
N,O-Didesmethylvenlafaxine,1TMS,isomer #2CNCC(C1=CC=C(O)C=C1)C1(O[Si](C)(C)C)CCCCC12215.4Semi standard non polar33892256
N,O-Didesmethylvenlafaxine,1TMS,isomer #3CN(CC(C1=CC=C(O)C=C1)C1(O)CCCCC1)[Si](C)(C)C2384.8Semi standard non polar33892256
N,O-Didesmethylvenlafaxine,2TMS,isomer #1CNCC(C1=CC=C(O[Si](C)(C)C)C=C1)C1(O[Si](C)(C)C)CCCCC12147.0Semi standard non polar33892256
N,O-Didesmethylvenlafaxine,2TMS,isomer #2CN(CC(C1=CC=C(O[Si](C)(C)C)C=C1)C1(O)CCCCC1)[Si](C)(C)C2330.1Semi standard non polar33892256
N,O-Didesmethylvenlafaxine,2TMS,isomer #3CN(CC(C1=CC=C(O)C=C1)C1(O[Si](C)(C)C)CCCCC1)[Si](C)(C)C2387.4Semi standard non polar33892256
N,O-Didesmethylvenlafaxine,3TMS,isomer #1CN(CC(C1=CC=C(O[Si](C)(C)C)C=C1)C1(O[Si](C)(C)C)CCCCC1)[Si](C)(C)C2337.6Semi standard non polar33892256
N,O-Didesmethylvenlafaxine,3TMS,isomer #1CN(CC(C1=CC=C(O[Si](C)(C)C)C=C1)C1(O[Si](C)(C)C)CCCCC1)[Si](C)(C)C2314.4Standard non polar33892256
N,O-Didesmethylvenlafaxine,3TMS,isomer #1CN(CC(C1=CC=C(O[Si](C)(C)C)C=C1)C1(O[Si](C)(C)C)CCCCC1)[Si](C)(C)C2466.8Standard polar33892256
N,O-Didesmethylvenlafaxine,1TBDMS,isomer #1CNCC(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C1(O)CCCCC12464.7Semi standard non polar33892256
N,O-Didesmethylvenlafaxine,1TBDMS,isomer #2CNCC(C1=CC=C(O)C=C1)C1(O[Si](C)(C)C(C)(C)C)CCCCC12459.0Semi standard non polar33892256
N,O-Didesmethylvenlafaxine,1TBDMS,isomer #3CN(CC(C1=CC=C(O)C=C1)C1(O)CCCCC1)[Si](C)(C)C(C)(C)C2606.8Semi standard non polar33892256
N,O-Didesmethylvenlafaxine,2TBDMS,isomer #1CNCC(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C1(O[Si](C)(C)C(C)(C)C)CCCCC12647.4Semi standard non polar33892256
N,O-Didesmethylvenlafaxine,2TBDMS,isomer #2CN(CC(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C1(O)CCCCC1)[Si](C)(C)C(C)(C)C2820.0Semi standard non polar33892256
N,O-Didesmethylvenlafaxine,2TBDMS,isomer #3CN(CC(C1=CC=C(O)C=C1)C1(O[Si](C)(C)C(C)(C)C)CCCCC1)[Si](C)(C)C(C)(C)C2867.8Semi standard non polar33892256
N,O-Didesmethylvenlafaxine,3TBDMS,isomer #1CN(CC(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C1(O[Si](C)(C)C(C)(C)C)CCCCC1)[Si](C)(C)C(C)(C)C3074.3Semi standard non polar33892256
N,O-Didesmethylvenlafaxine,3TBDMS,isomer #1CN(CC(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C1(O[Si](C)(C)C(C)(C)C)CCCCC1)[Si](C)(C)C(C)(C)C2918.4Standard non polar33892256
N,O-Didesmethylvenlafaxine,3TBDMS,isomer #1CN(CC(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C1(O[Si](C)(C)C(C)(C)C)CCCCC1)[Si](C)(C)C(C)(C)C2748.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N,O-Didesmethylvenlafaxine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9110000000-cbd10b1dd6d4905b23e72017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N,O-Didesmethylvenlafaxine GC-MS (2 TMS) - 70eV, Positivesplash10-0096-9426000000-61a7872d2c122cd397a72017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N,O-Didesmethylvenlafaxine 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 - N,O-Didesmethylvenlafaxine LC-ESI-QTOF , positive-QTOFsplash10-0udi-0090000000-18b0ff9f4effb427c8502017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N,O-Didesmethylvenlafaxine LC-ESI-QTOF , positive-QTOFsplash10-0f89-0690000000-76320180caa85165ea302017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N,O-Didesmethylvenlafaxine LC-ESI-QTOF , positive-QTOFsplash10-001i-0900000000-972812599a864da2c2d62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N,O-Didesmethylvenlafaxine LC-ESI-QTOF , positive-QTOFsplash10-001i-0900000000-71e0dd0536493974cab32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N,O-Didesmethylvenlafaxine LC-ESI-QTOF , positive-QTOFsplash10-001l-0900000000-128aee8e6952b29a0c042017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N,O-Didesmethylvenlafaxine LC-ESI-ITFT , positive-QTOFsplash10-001i-0090000000-53bef76e53f1bb71dc482017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N,O-Didesmethylvenlafaxine LC-ESI-ITFT , positive-QTOFsplash10-0udi-0090000000-a2152632c4f5d9dd0fdc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N,O-Didesmethylvenlafaxine LC-ESI-ITFT , positive-QTOFsplash10-0f89-0190000000-14f268c2233e093057be2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N,O-Didesmethylvenlafaxine LC-ESI-ITFT , positive-QTOFsplash10-0kai-0930000000-492c20d8ef104c812bc42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N,O-Didesmethylvenlafaxine LC-ESI-ITFT , positive-QTOFsplash10-0a59-0900000000-270526729348694faec52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N,O-Didesmethylvenlafaxine LC-ESI-ITFT , positive-QTOFsplash10-0a4i-0900000000-49d9cecee89a0891f2a42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N,O-Didesmethylvenlafaxine LC-ESI-ITFT , positive-QTOFsplash10-0a4i-1900000000-98ff40e65ce934d72ad72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N,O-Didesmethylvenlafaxine LC-ESI-ITFT , positive-QTOFsplash10-0udi-0090000000-f48491c9fc80a5afefe22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N,O-Didesmethylvenlafaxine LC-ESI-ITFT , positive-QTOFsplash10-0ue9-0190000000-fd853c2050c38ad4402e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N,O-Didesmethylvenlafaxine LC-ESI-ITFT , positive-QTOFsplash10-0kai-0940000000-15959e593351a407bd4c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N,O-Didesmethylvenlafaxine LC-ESI-ITFT , positive-QTOFsplash10-0a59-0900000000-e5e2cf0da0edf47ab09a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N,O-Didesmethylvenlafaxine LC-ESI-ITFT , positive-QTOFsplash10-0a59-1900000000-8094ea6607b59d8d36b92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N,O-Didesmethylvenlafaxine LC-ESI-ITFT , positive-QTOFsplash10-0a4i-1900000000-1e5db5ab45ceb1c314da2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N,O-Didesmethylvenlafaxine LC-ESI-ITFT , positive-QTOFsplash10-001i-0090000000-b79dbb6b27e563ee2ea22017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N,O-Didesmethylvenlafaxine 10V, Positive-QTOFsplash10-0ue9-0090000000-79c59109bf3cfab20db12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N,O-Didesmethylvenlafaxine 20V, Positive-QTOFsplash10-0uxr-3190000000-c1cae5e86c59e8ff41f12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N,O-Didesmethylvenlafaxine 40V, Positive-QTOFsplash10-1003-9120000000-b8993698d8a165df78222016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N,O-Didesmethylvenlafaxine 10V, Negative-QTOFsplash10-0002-1090000000-5e188699f1113797b84d2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N,O-Didesmethylvenlafaxine 20V, Negative-QTOFsplash10-0f7k-1490000000-4c22c19ddc61f12e910d2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N,O-Didesmethylvenlafaxine 40V, Negative-QTOFsplash10-0536-9820000000-a44af91c9bb5b55cb2a52016-08-04Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
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 Compound3451347
PDB IDNot Available
ChEBI ID83529
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