Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-06-12 17:33:41 UTC
Update Date2021-09-14 15:46:18 UTC
HMDB IDHMDB0060552
Secondary Accession Numbers
  • HMDB60552
Metabolite Identification
Common NameDextrorphan
DescriptionDextrorphan is a metabolite of Dextromethorphan. Dextrorphan (DXO) is a psychoactive drug of the morphinan chemical class which acts as an antitussive or cough suppressant and dissociative hallucinogen. It is the dextro-stereoisomer of racemorphan, the levo-half being levorphanol. Dextrorphan is produced by O-demethylation of dextromethorphan by CYP2D6. Dextrorphan is an NMDA antagonist and contributes to the psychoactive effects of dextromethorphan. (Wikipedia )
Structure
Data?1563866075
Synonyms
ValueSource
(+)-3-Hydroxy-N-methylmorphinanChEBI
D-3-Hydroxy-N-methylmorphinanChEBI
DextrorphaneChEBI
DextrorphanumChEBI
(+-)-17-Methylmorphinan-3-olHMDB
Chemical FormulaC17H23NO
Average Molecular Weight257.3706
Monoisotopic Molecular Weight257.177964363
IUPAC Name(1S,9S,10S)-17-methyl-17-azatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2(7),3,5-trien-4-ol
Traditional Namedextrorphan
CAS Registry NumberNot Available
SMILES
CN1CC[C@@]23CCCC[C@@H]2[C@@H]1CC1=C3C=C(O)C=C1
InChI Identifier
InChI=1S/C17H23NO/c1-18-9-8-17-7-3-2-4-14(17)16(18)10-12-5-6-13(19)11-15(12)17/h5-6,11,14,16,19H,2-4,7-10H2,1H3/t14-,16+,17+/m1/s1
InChI KeyJAQUASYNZVUNQP-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
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Piperidine
  • Benzenoid
  • Tertiary aliphatic amine
  • Tertiary amine
  • Organoheterocyclic compound
  • Azacycle
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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 Solubility0.17 g/LALOGPS
logP3.29ALOGPS
logP2.9ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)10.46ChemAxon
pKa (Strongest Basic)9.66ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area23.47 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity78.08 m³·mol⁻¹ChemAxon
Polarizability29.7 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]+160.80131661259
DarkChem[M-H]-158.58431661259
DeepCCS[M-2H]-202.70930932474
DeepCCS[M+Na]+177.93630932474
AllCCS[M+H]+163.732859911
AllCCS[M+H-H2O]+160.132859911
AllCCS[M+NH4]+167.032859911
AllCCS[M+Na]+167.932859911
AllCCS[M-H]-170.132859911
AllCCS[M+Na-2H]-169.932859911
AllCCS[M+HCOO]-169.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DextrorphanCN1CC[C@@]23CCCC[C@@H]2[C@@H]1CC1=C3C=C(O)C=C13384.8Standard polar33892256
DextrorphanCN1CC[C@@]23CCCC[C@@H]2[C@@H]1CC1=C3C=C(O)C=C12303.8Standard non polar33892256
DextrorphanCN1CC[C@@]23CCCC[C@@H]2[C@@H]1CC1=C3C=C(O)C=C12223.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Dextrorphan,1TMS,isomer #1CN1CC[C@@]23CCCC[C@@H]2[C@@H]1CC1=CC=C(O[Si](C)(C)C)C=C132204.7Semi standard non polar33892256
Dextrorphan,1TBDMS,isomer #1CN1CC[C@@]23CCCC[C@@H]2[C@@H]1CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C132498.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Dextrorphan GC-MS (Non-derivatized) - 70eV, Positivesplash10-02bf-0090000000-12982ec002fb66d8d2542017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dextrorphan GC-MS (1 TMS) - 70eV, Positivesplash10-0hbi-2096000000-da9354b628843987f1422017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dextrorphan 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 - Dextrorphan , positive-QTOFsplash10-0a4i-1590000000-b308de853cbd223599272017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dextrorphan 35V, Positive-QTOFsplash10-0a4i-0970000000-1b6c27a0893f6ca3200b2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dextrorphan 10V, Positive-QTOFsplash10-0a4i-0090000000-6ba0fc98a8d249fe2da02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dextrorphan 20V, Positive-QTOFsplash10-0a4i-0090000000-d3e64fd4fd1d790a54bb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dextrorphan 40V, Positive-QTOFsplash10-0596-6790000000-7a77fc910d8d984d10122016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dextrorphan 10V, Negative-QTOFsplash10-0a4i-0090000000-503f808754310f6363732016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dextrorphan 20V, Negative-QTOFsplash10-0a4i-0090000000-bce69f729c40b2f3bed92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dextrorphan 40V, Negative-QTOFsplash10-002g-1290000000-97ee80b268d9fa4de6792016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dextrorphan 10V, Positive-QTOFsplash10-0a4i-0090000000-07569ae87a2b34cbffc02021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dextrorphan 20V, Positive-QTOFsplash10-0a4i-0090000000-2ae58a148c800ebf61b02021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dextrorphan 40V, Positive-QTOFsplash10-03di-1890000000-ba7be4c45f7ec0c83cce2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dextrorphan 10V, Negative-QTOFsplash10-0a4i-0090000000-4d2203d29a4418e5d7732021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dextrorphan 20V, Negative-QTOFsplash10-0a4i-0090000000-4d2203d29a4418e5d7732021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dextrorphan 40V, Negative-QTOFsplash10-0002-0960000000-e8715b9d7acb44e50afb2021-10-12Wishart 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 LinkDextrorphan
METLIN IDNot Available
PubChem Compound5360697
PDB IDNot Available
ChEBI ID29133
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