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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-06-18 17:47:51 UTC
Update Date2021-09-14 15:19:07 UTC
HMDB IDHMDB0060657
Secondary Accession Numbers
  • HMDB60657
Metabolite Identification
Common NameNorcodeine
DescriptionNorcodeine, also known as N-demethylcodeine, 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. Norcodeine is a very strong basic compound (based on its pKa). Norcodeine has relatively little opioid activity in its own right, but is formed as a metabolite of codeine following ingestion. norcodeine and formaldehyde can be biosynthesized from codeine; which is catalyzed by the enzyme cytochrome P450 3A4. In humans, norcodeine is involved in codeine metabolism pathway. Norcodeine is a metabolite of codeine. Norcodeine is an opiate analogue that is the N-demethylated derivative of codeine.
Structure
Data?1563866088
Synonyms
ValueSource
(-)-N-NorcodeineChEBI
N-DemethylcodeineChEBI
N-DesmethylcodeineChEBI
NorcodeinaChEBI
NorcodeinumChEBI
Norcodeine hydrochlorideHMDB
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
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
  • 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
Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

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 Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM166.130932474
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.38 g/LALOGPS
logP10(0.99) g/LALOGPS
logP10(0.96) g/LChemAxon
logS10(-2.9) g/LALOGPS
pKa (Strongest Acidic)13.78ChemAxon
pKa (Strongest Basic)10.07ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area50.72 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity79.31 m³·mol⁻¹ChemAxon
Polarizability29.76 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]+167.88331661259
DarkChem[M-H]-165.92631661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Norcodeine[H][C@]12C=C[C@H](O)[C@@H]3OC4=C5C(C[C@H]1NCC[C@@]235)=CC=C4OC3852.8Standard polar33892256
Norcodeine[H][C@]12C=C[C@H](O)[C@@H]3OC4=C5C(C[C@H]1NCC[C@@]235)=CC=C4OC2329.3Standard non polar33892256
Norcodeine[H][C@]12C=C[C@H](O)[C@@H]3OC4=C5C(C[C@H]1NCC[C@@]235)=CC=C4OC2511.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Norcodeine,1TMS,isomer #1COC1=CC=C2C[C@H]3NCC[C@]45C2=C1O[C@H]4[C@@H](O[Si](C)(C)C)C=C[C@@H]352458.7Semi standard non polar33892256
Norcodeine,1TMS,isomer #2COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O)[C@@H]5OC1=C2[C@@]54CCN3[Si](C)(C)C2485.8Semi standard non polar33892256
Norcodeine,2TMS,isomer #1COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[Si](C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3[Si](C)(C)C2494.6Semi standard non polar33892256
Norcodeine,2TMS,isomer #1COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[Si](C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3[Si](C)(C)C2565.0Standard non polar33892256
Norcodeine,2TMS,isomer #1COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[Si](C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3[Si](C)(C)C3033.2Standard polar33892256
Norcodeine,1TBDMS,isomer #1COC1=CC=C2C[C@H]3NCC[C@]45C2=C1O[C@H]4[C@@H](O[Si](C)(C)C(C)(C)C)C=C[C@@H]352727.3Semi standard non polar33892256
Norcodeine,1TBDMS,isomer #2COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O)[C@@H]5OC1=C2[C@@]54CCN3[Si](C)(C)C(C)(C)C2707.3Semi standard non polar33892256
Norcodeine,2TBDMS,isomer #1COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3[Si](C)(C)C(C)(C)C2956.5Semi standard non polar33892256
Norcodeine,2TBDMS,isomer #1COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3[Si](C)(C)C(C)(C)C3039.7Standard non polar33892256
Norcodeine,2TBDMS,isomer #1COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3[Si](C)(C)C(C)(C)C3281.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Norcodeine GC-MS (Non-derivatized) - 70eV, Positivesplash10-06fu-3090000000-def0952ab891094dac502017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Norcodeine GC-MS (1 TMS) - 70eV, Positivesplash10-006x-9024000000-4a5042616f41430320ca2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Norcodeine 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 - Norcodeine 10V, Positive-QTOFsplash10-000i-0090000000-2b2a065b9ef8042900852016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norcodeine 20V, Positive-QTOFsplash10-000i-0090000000-c4a4c893f35ec4ef5e422016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norcodeine 40V, Positive-QTOFsplash10-0pds-2290000000-77037cb876f15ead46142016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norcodeine 10V, Negative-QTOFsplash10-001i-0090000000-ef3058bd2e10c146303a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norcodeine 20V, Negative-QTOFsplash10-001i-0090000000-43f5eb0c5e5b500e33762016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norcodeine 40V, Negative-QTOFsplash10-02dj-0290000000-035b6759d7af2f780ae52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norcodeine 10V, Positive-QTOFsplash10-000i-0090000000-12d6d7cf9e71a6a9ec092021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norcodeine 20V, Positive-QTOFsplash10-000i-0090000000-541a4195765a2fac68a52021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norcodeine 40V, Positive-QTOFsplash10-00m0-0090000000-ffff010c1fecc953cf8f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norcodeine 10V, Negative-QTOFsplash10-001i-0090000000-793f02ff50658d83401d2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norcodeine 20V, Negative-QTOFsplash10-001i-0090000000-793f02ff50658d83401d2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norcodeine 40V, Negative-QTOFsplash10-001i-0090000000-b7393b65969f408660ab2021-10-12Wishart 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 IDC16576
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNorcodeine
METLIN IDNot Available
PubChem Compound9925873
PDB IDNot Available
ChEBI ID80579
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