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Record Information
Version4.0
Creation Date2013-06-18 17:47:51 UTC
Update Date2017-09-23 14:28:17 UTC
HMDB IDHMDB0060657
Secondary Accession Numbers
  • HMDB60657
Metabolite Identification
Common NameNorcodeine
DescriptionNorcodeine is a metabolite of codeine. Norcodeine is an opiate analogue that is the N-demethylated derivative of codeine. Norcodeine has relatively little opioid activity in its own right, but is formed as a metabolite of codeine following ingestion. (Wikipedia)
Structure
Thumb
Synonyms
ValueSource
(-)-N-NorcodeineChEBI
N-DemethylcodeineChEBI
N-DesmethylcodeineChEBI
NorcodeinaChEBI
NorcodeinumChEBI
Norcodeine hydrochlorideMeSH
Chemical FormulaC17H19NO3
Average Molecular Weight285.3377
Monoisotopic Molecular Weight285.136493479
IUPAC Name(1S,5R,13R,14S,17R)-10-methoxy-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7,9,11(18),15-tetraen-14-ol
Traditional NameN-norcodeine
CAS Registry NumberNot Available
SMILES
[H][C@]12C=C[C@H](O)[C@@H]3OC4=C5C(C[C@H]1NCC[C@@]235)=CC=C4OC
InChI Identifier
InChI=1S/C17H19NO3/c1-20-13-5-2-9-8-11-10-3-4-12(19)16-17(10,6-7-18-11)14(9)15(13)21-16/h2-5,10-12,16,18-19H,6-8H2,1H3/t10-,11+,12-,16-,17-/m0/s1
InChI KeyHKOIXWVRNLGFOR-KOFBORESSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassAlkaloids and derivatives
Sub ClassMorphinans
Direct ParentMorphinans
Alternative Parents
Substituents
  • Morphinan
  • Phenanthrene
  • Tetralin
  • Coumaran
  • Anisole
  • Alkyl aryl ether
  • Aralkylamine
  • Piperidine
  • Benzenoid
  • Secondary alcohol
  • Secondary aliphatic amine
  • Ether
  • Oxacycle
  • Azacycle
  • Secondary amine
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Amine
  • Organic oxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
  • Endogenous
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
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 Solubility0.38 mg/mLALOGPS
logP0.99ALOGPS
logP0.96ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)13.78ChemAxon
pKa (Strongest Basic)10.07ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area50.72 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity79.31 m3·mol-1ChemAxon
Polarizability29.76 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB/PathwhizKEGG
Codeine Metabolism PathwayPw000597Pw000597 greyscalePw000597 simpleNot Available
Codeine PathwayPw000411Pw000411 greyscalePw000411 simpleNot Available
Displaying all 2 entries
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      DrugBank Metabolite IDDBMET00340
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDC16576
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      NuGOwiki LinkHMDB0060657
      METLIN IDNot Available
      PubChem Compound9925873
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available