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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:50:07 UTC
Update Date2019-07-23 06:35:18 UTC
HMDB IDHMDB0041960
Secondary Accession Numbers
  • HMDB41960
Metabolite Identification
Common NameNoroxycodone
DescriptionNoroxycodone 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. Noroxycodone binds to and activates the μ-opioid receptor (MOR) similarly to oxycodone, although with one-third of the affinity of oxycodone and 5- to 10-fold lower activational potency. Noroxycodone is a very strong basic compound (based on its pKa). Noroxycodone is the major metabolite of the opioid analgesic oxycodone. However, although a potent MOR agonist, noroxycodone poorly crosses the blood-brain-barrier into the central nervous system, and for this reason, is only minimally analgesic in comparison. It is formed from oxycodone in the liver via N-demethylation predominantly by CYP3A4.
Structure
Data?1563863718
Synonyms
ValueSource
NoroxycodoneMeSH
Chemical FormulaC17H19NO4
Average Molecular Weight301.3371
Monoisotopic Molecular Weight301.131408101
IUPAC Name(1S,5R,13R,17S)-17-hydroxy-10-methoxy-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10-trien-14-one
Traditional Name(1S,5R,13R,17S)-17-hydroxy-10-methoxy-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10-trien-14-one
CAS Registry Number57664-96-7
SMILES
[H][C@@]12OC3=C(OC)C=CC4=C3[C@@]11CCN[C@]([H])(C4)[C@]1(O)CCC2=O
InChI Identifier
InChI=1S/C17H19NO4/c1-21-11-3-2-9-8-12-17(20)5-4-10(19)15-16(17,6-7-18-12)13(9)14(11)22-15/h2-3,12,15,18,20H,4-8H2,1H3/t12-,15+,16+,17-/m1/s1
InChI KeyRIKMCJUNPCRFMW-ISWURRPUSA-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
  • Isoquinolone
  • Tetralin
  • Coumaran
  • Anisole
  • Alkyl aryl ether
  • Aralkylamine
  • Piperidine
  • Cyclic alcohol
  • Tertiary alcohol
  • 1,2-aminoalcohol
  • Ketone
  • Oxacycle
  • Azacycle
  • Secondary amine
  • Organoheterocyclic compound
  • Secondary aliphatic amine
  • Ether
  • Alcohol
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Source:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility5.22 g/LALOGPS
logP0.64ALOGPS
logP0.65ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)13.57ChemAxon
pKa (Strongest Basic)9.48ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area67.79 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity78.75 m³·mol⁻¹ChemAxon
Polarizability30.74 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-9070000000-4abba3f79f8f09f4630cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0ab9-9015000000-d37711ee5edd1c834db9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-0095000000-e274b3de5183f77d69f0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0091000000-b9baf79e66376f7f4d5aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pxr-2090000000-6bc1cb98a21ae331bfeeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0029000000-0b59ccdf4eb8caa1413fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f89-0097000000-9e8a88ce6d0cc295b3eaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06u6-1090000000-3d7a5ac9b7838574bd55Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
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 ID4590081
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNoroxycodone
METLIN IDNot Available
PubChem Compound5489120
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available