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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:00:56 UTC
Update Date2021-09-14 15:47:58 UTC
HMDB IDHMDB0014045
Secondary Accession Numbers
  • HMDB14045
Metabolite Identification
Common Name3-Methoxymorphinan
Description3-Methoxymorphinan is only found in individuals that have used or taken Dextromethorphan. 3-Methoxymorphinan is a metabolite of Dextromethorphan. 3-methoxymorphinan belongs to the family of Morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic.
Structure
Data?1582753163
Synonyms
ValueSource
3-Methoxymorphinan hydrochlorideHMDB
3-Methoxymorphinan hydrochloride, (14alpha)-(+-)-isomerHMDB
3-Methoxymorphinan, (+-)-isomerHMDB
3-Methoxymorphinan, (14alpha)-(+-)-isomerHMDB
3-Methoxymorphinan, (14alpha)-isomerHMDB
LK-3 CompoundHMDB
3-Methoxymorphinan hydrobromide, (9alpha,13alpha,14alpha)-isomerHMDB
3-Methoxymorphinan hydrochloride, (14alpha)-isomerHMDB
3-Methoxymorphinan, (9alpha,13alpha,14alpha)-isomerHMDB
3-MethoxymorphinanMeSH
Chemical FormulaC17H23NO
Average Molecular Weight257.3706
Monoisotopic Molecular Weight257.177964363
IUPAC Name(1S,9S,10S)-4-methoxy-17-azatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2(7),3,5-triene
Traditional Name(1S,9S,10S)-4-methoxy-17-azatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2(7),3,5-triene
CAS Registry Number1531-25-5
SMILES
COC1=CC2=C(C[C@@H]3NCC[C@]22CCCC[C@H]32)C=C1
InChI Identifier
InChI=1S/C17H23NO/c1-19-13-6-5-12-10-16-14-4-2-3-7-17(14,8-9-18-16)15(12)11-13/h5-6,11,14,16,18H,2-4,7-10H2,1H3/t14-,16+,17+/m1/s1
InChI KeyILNSWVUXAPSPEH-PVAVHDDUSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassMorphinans
Sub ClassNot Available
Direct ParentMorphinans
Alternative Parents
Substituents
  • Morphinan
  • Phenanthrene
  • Benzazocine
  • Tetralin
  • Anisole
  • Alkyl aryl ether
  • Aralkylamine
  • Piperidine
  • Benzenoid
  • Secondary aliphatic amine
  • Ether
  • Azacycle
  • Secondary amine
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Amine
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

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 Solubility0.0027 g/LALOGPS
logP3.8ALOGPS
logP3.11ChemAxon
logS-5ALOGPS
pKa (Strongest Basic)10.22ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area21.26 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity77.27 m³·mol⁻¹ChemAxon
Polarizability29.61 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+160.96531661259
DarkChem[M-H]-160.98831661259
DeepCCS[M-2H]-203.59330932474
DeepCCS[M+Na]+178.8230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-MethoxymorphinanCOC1=CC2=C(C[C@@H]3NCC[C@]22CCCC[C@H]32)C=C13225.0Standard polar33892256
3-MethoxymorphinanCOC1=CC2=C(C[C@@H]3NCC[C@]22CCCC[C@H]32)C=C12152.5Standard non polar33892256
3-MethoxymorphinanCOC1=CC2=C(C[C@@H]3NCC[C@]22CCCC[C@H]32)C=C12212.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Methoxymorphinan,1TMS,isomer #1COC1=CC=C2C[C@H]3[C@H]4CCCC[C@@]4(CCN3[Si](C)(C)C)C2=C12257.2Semi standard non polar33892256
3-Methoxymorphinan,1TMS,isomer #1COC1=CC=C2C[C@H]3[C@H]4CCCC[C@@]4(CCN3[Si](C)(C)C)C2=C12345.5Standard non polar33892256
3-Methoxymorphinan,1TMS,isomer #1COC1=CC=C2C[C@H]3[C@H]4CCCC[C@@]4(CCN3[Si](C)(C)C)C2=C12744.8Standard polar33892256
3-Methoxymorphinan,1TBDMS,isomer #1COC1=CC=C2C[C@H]3[C@H]4CCCC[C@@]4(CCN3[Si](C)(C)C(C)(C)C)C2=C12477.0Semi standard non polar33892256
3-Methoxymorphinan,1TBDMS,isomer #1COC1=CC=C2C[C@H]3[C@H]4CCCC[C@@]4(CCN3[Si](C)(C)C(C)(C)C)C2=C12599.2Standard non polar33892256
3-Methoxymorphinan,1TBDMS,isomer #1COC1=CC=C2C[C@H]3[C@H]4CCCC[C@@]4(CCN3[Si](C)(C)C(C)(C)C)C2=C12921.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methoxymorphinan GC-MS (Non-derivatized) - 70eV, Positivesplash10-00ou-0090000000-02c7b32ac3081ebf59232017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methoxymorphinan 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 - 3-Methoxymorphinan 10V, Positive-QTOFsplash10-0a4i-0090000000-f0acbe633f1ef78e72162016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxymorphinan 20V, Positive-QTOFsplash10-0a4i-0090000000-54662e3182c9397141612016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxymorphinan 40V, Positive-QTOFsplash10-000f-5970000000-35b194f29f27675f40cd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxymorphinan 10V, Negative-QTOFsplash10-0a4i-0090000000-089e7bdb4af372e7486c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxymorphinan 20V, Negative-QTOFsplash10-0a4i-0090000000-905d2c5b908a1ef3c9c52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxymorphinan 40V, Negative-QTOFsplash10-0006-0290000000-d37c96e4f09b8d5606252016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxymorphinan 10V, Positive-QTOFsplash10-0a4i-0090000000-07569ae87a2b34cbffc02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxymorphinan 20V, Positive-QTOFsplash10-0a4i-0190000000-1cb112d5f9e3bc10fa012021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxymorphinan 40V, Positive-QTOFsplash10-07er-0890000000-5131521492963ed9e0052021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxymorphinan 10V, Negative-QTOFsplash10-0a4i-0090000000-4d2203d29a4418e5d7732021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxymorphinan 20V, Negative-QTOFsplash10-0a4i-0090000000-2c191d5d743de9bed35d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxymorphinan 40V, Negative-QTOFsplash10-0udi-0090000000-e25cdc87cd670c87eff32021-09-22Wishart 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 ID24693630
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link3-Methoxymorphinan
METLIN IDNot Available
PubChem Compound6603912
PDB IDNot Available
ChEBI ID580449
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