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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:16:56 UTC
Update Date2021-09-14 15:19:57 UTC
HMDB IDHMDB0061077
Secondary Accession Numbers
  • HMDB61077
Metabolite Identification
Common Namealpha-oxycodol
Descriptionalpha-oxycodol is a metabolite of oxymorphone. Oxymorphone (Opana, Numorphan, Numorphone) or 14-Hydroxydihydromorphinone is a powerful semi-synthetic opioid analgesic first developed in Germany in 1914, patented in the USA by Endo Pharmaceuticals in 1955 and introduced to the United States market in January 1959 and other countries around the same time. It (along with hydromorphone) was designed to have less incidence of side effects than morphine and heroin. (Wikipedia)
Structure
Data?1563866143
Synonyms
ValueSource
a-OxycodolGenerator
Α-oxycodolGenerator
Chemical FormulaC18H23NO4
Average Molecular Weight317.3795
Monoisotopic Molecular Weight317.162708229
IUPAC Name(1S,13R,14S,17S)-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10-triene-14,17-diol
Traditional Name(1S,13R,14S,17S)-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10-triene-14,17-diol
CAS Registry NumberNot Available
SMILES
[H]C12CC3=C4C(O[C@H]5[C@@H](O)CC[C@]1(O)[C@@]45CCN2C)=C(OC)C=C3
InChI Identifier
InChI=1S/C18H23NO4/c1-19-8-7-17-14-10-3-4-12(22-2)15(14)23-16(17)11(20)5-6-18(17,21)13(19)9-10/h3-4,11,13,16,20-21H,5-9H2,1-2H3/t11-,13?,16-,17-,18+/m0/s1
InChI KeyLHTAJTFGGUDLRH-FHHXKLHRSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenanthrenes and derivatives
Sub ClassNot Available
Direct ParentPhenanthrenes and derivatives
Alternative Parents
Substituents
  • Phenanthrene
  • Tetralin
  • Coumaran
  • Anisole
  • Alkyl aryl ether
  • Aralkylamine
  • Piperidine
  • Cyclic alcohol
  • Tertiary alcohol
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Ether
  • Alcohol
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • 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 Solubility3.73 g/LALOGPS
logP1.15ALOGPS
logP0.62ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)13.48ChemAxon
pKa (Strongest Basic)8.92ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area62.16 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity84.94 m³·mol⁻¹ChemAxon
Polarizability33.58 ųChemAxon
Number of Rings5ChemAxon
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]+174.41231661259
DarkChem[M-H]-170.94331661259
DeepCCS[M-2H]-218.45330932474
DeepCCS[M+Na]+193.38330932474
AllCCS[M+H]+176.832859911
AllCCS[M+H-H2O]+173.832859911
AllCCS[M+NH4]+179.732859911
AllCCS[M+Na]+180.532859911
AllCCS[M-H]-180.932859911
AllCCS[M+Na-2H]-180.632859911
AllCCS[M+HCOO]-180.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
alpha-oxycodol[H]C12CC3=C4C(O[C@H]5[C@@H](O)CC[C@]1(O)[C@@]45CCN2C)=C(OC)C=C33828.6Standard polar33892256
alpha-oxycodol[H]C12CC3=C4C(O[C@H]5[C@@H](O)CC[C@]1(O)[C@@]45CCN2C)=C(OC)C=C32464.3Standard non polar33892256
alpha-oxycodol[H]C12CC3=C4C(O[C@H]5[C@@H](O)CC[C@]1(O)[C@@]45CCN2C)=C(OC)C=C32644.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
alpha-oxycodol,1TMS,isomer #1COC1=CC=C2CC3N(C)CC[C@]45C2=C1O[C@H]4[C@@H](O[Si](C)(C)C)CC[C@@]35O2541.3Semi standard non polar33892256
alpha-oxycodol,1TMS,isomer #2COC1=CC=C2CC3N(C)CC[C@]45C2=C1O[C@H]4[C@@H](O)CC[C@@]35O[Si](C)(C)C2520.3Semi standard non polar33892256
alpha-oxycodol,2TMS,isomer #1COC1=CC=C2CC3N(C)CC[C@]45C2=C1O[C@H]4[C@@H](O[Si](C)(C)C)CC[C@@]35O[Si](C)(C)C2532.1Semi standard non polar33892256
alpha-oxycodol,1TBDMS,isomer #1COC1=CC=C2CC3N(C)CC[C@]45C2=C1O[C@H]4[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@@]35O2804.6Semi standard non polar33892256
alpha-oxycodol,1TBDMS,isomer #2COC1=CC=C2CC3N(C)CC[C@]45C2=C1O[C@H]4[C@@H](O)CC[C@@]35O[Si](C)(C)C(C)(C)C2780.4Semi standard non polar33892256
alpha-oxycodol,2TBDMS,isomer #1COC1=CC=C2CC3N(C)CC[C@]45C2=C1O[C@H]4[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@@]35O[Si](C)(C)C(C)(C)C2995.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - alpha-oxycodol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fb9-9053000000-d776af02f95fedb77ebc2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-oxycodol GC-MS (2 TMS) - 70eV, Positivesplash10-0092-9304700000-035759e78222150f98be2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-oxycodol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-oxycodol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-oxycodol GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-oxycodol GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-oxycodol GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-oxycodol GC-MS ("alpha-oxycodol,1TMS,#2" TMS) - 70eV, PositiveNot Available2021-10-14Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-oxycodol 10V, Positive-QTOFsplash10-0uxr-0019000000-d5ac70e4c11876542f822017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-oxycodol 20V, Positive-QTOFsplash10-0udi-1049000000-bb80511f392bdee5ab742017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-oxycodol 40V, Positive-QTOFsplash10-001i-3091000000-e856c7c6e9d4e60e58eb2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-oxycodol 10V, Negative-QTOFsplash10-014i-0029000000-e9d3f5e6652033cabfd62017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-oxycodol 20V, Negative-QTOFsplash10-014j-0089000000-819cc0d07b674251aa792017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-oxycodol 40V, Negative-QTOFsplash10-0006-1090000000-711121f1dacb8067e0ad2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-oxycodol 10V, Negative-QTOFsplash10-014i-0009000000-3fe3b20def364ac29f1a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-oxycodol 20V, Negative-QTOFsplash10-014i-0009000000-3fe3b20def364ac29f1a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-oxycodol 40V, Negative-QTOFsplash10-03di-0029000000-b869712e421d8db698f12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-oxycodol 10V, Positive-QTOFsplash10-014i-0009000000-ab8d4424adfeb148250f2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-oxycodol 20V, Positive-QTOFsplash10-014i-0019000000-ac62b6a7e1fe2ea950ea2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-oxycodol 40V, Positive-QTOFsplash10-0j4i-0093000000-baed767c66bcdb23e1fb2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart 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 Compound69087507
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