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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-06-18 17:39:39 UTC
Update Date2019-07-23 07:14:47 UTC
HMDB IDHMDB0060651
Secondary Accession Numbers
  • HMDB60651
Metabolite Identification
Common Name2-Hydroxycarbamazepine
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. A morphinane-like compound that is the N-demethylated derivative of codeine. Norcodeine is a very strong basic compound (based on its pKa). 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.
Structure
Data?1563866087
Synonyms
ValueSource
(-)-N-NorcodeineChEBI
N-DemethylcodeineChEBI
N-DesmethylcodeineChEBI
NorcodeinaChEBI
NorcodeinumChEBI
Norcodeine hydrochlorideHMDB
Chemical FormulaC15H12N2O2
Average Molecular Weight252.268
Monoisotopic Molecular Weight252.089877638
IUPAC Name6-hydroxy-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,9,11,13-heptaene-2-carboxamide
Traditional Name6-hydroxy-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,9,11,13-heptaene-2-carboxamide
CAS Registry NumberNot Available
SMILES
NC(=O)N1C2=CC=CC=C2C=CC2=CC(O)=CC=C12
InChI Identifier
InChI=1S/C15H12N2O2/c16-15(19)17-13-4-2-1-3-10(13)5-6-11-9-12(18)7-8-14(11)17/h1-9,18H,(H2,16,19)
InChI KeyVPZIYMMSJFWLSP-UHFFFAOYSA-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 PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP10(2.21) g/LALOGPS
logP10(2.46) g/LChemAxon
logS10(-3.3) g/LALOGPS
pKa (Strongest Acidic)9.15ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.56 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity73.87 m³·mol⁻¹ChemAxon
Polarizability26.06 ųChemAxon
Number of Rings3ChemAxon
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]+157.63331661259
DarkChem[M-H]-156.02331661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-HydroxycarbamazepineNC(=O)N1C2=CC=CC=C2C=CC2=CC(O)=CC=C124187.1Standard polar33892256
2-HydroxycarbamazepineNC(=O)N1C2=CC=CC=C2C=CC2=CC(O)=CC=C122409.3Standard non polar33892256
2-HydroxycarbamazepineNC(=O)N1C2=CC=CC=C2C=CC2=CC(O)=CC=C122685.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Hydroxycarbamazepine,1TMS,isomer #1C[Si](C)(C)OC1=CC=C2C(=C1)C=CC1=CC=CC=C1N2C(N)=O2535.9Semi standard non polar33892256
2-Hydroxycarbamazepine,1TMS,isomer #2C[Si](C)(C)NC(=O)N1C2=CC=CC=C2C=CC2=CC(O)=CC=C212523.1Semi standard non polar33892256
2-Hydroxycarbamazepine,2TMS,isomer #1C[Si](C)(C)NC(=O)N1C2=CC=CC=C2C=CC2=CC(O[Si](C)(C)C)=CC=C212497.6Semi standard non polar33892256
2-Hydroxycarbamazepine,2TMS,isomer #1C[Si](C)(C)NC(=O)N1C2=CC=CC=C2C=CC2=CC(O[Si](C)(C)C)=CC=C212485.2Standard non polar33892256
2-Hydroxycarbamazepine,2TMS,isomer #1C[Si](C)(C)NC(=O)N1C2=CC=CC=C2C=CC2=CC(O[Si](C)(C)C)=CC=C213448.5Standard polar33892256
2-Hydroxycarbamazepine,2TMS,isomer #2C[Si](C)(C)N(C(=O)N1C2=CC=CC=C2C=CC2=CC(O)=CC=C21)[Si](C)(C)C2587.7Semi standard non polar33892256
2-Hydroxycarbamazepine,2TMS,isomer #2C[Si](C)(C)N(C(=O)N1C2=CC=CC=C2C=CC2=CC(O)=CC=C21)[Si](C)(C)C2726.4Standard non polar33892256
2-Hydroxycarbamazepine,2TMS,isomer #2C[Si](C)(C)N(C(=O)N1C2=CC=CC=C2C=CC2=CC(O)=CC=C21)[Si](C)(C)C3661.4Standard polar33892256
2-Hydroxycarbamazepine,3TMS,isomer #1C[Si](C)(C)OC1=CC=C2C(=C1)C=CC1=CC=CC=C1N2C(=O)N([Si](C)(C)C)[Si](C)(C)C2565.2Semi standard non polar33892256
2-Hydroxycarbamazepine,3TMS,isomer #1C[Si](C)(C)OC1=CC=C2C(=C1)C=CC1=CC=CC=C1N2C(=O)N([Si](C)(C)C)[Si](C)(C)C2744.5Standard non polar33892256
2-Hydroxycarbamazepine,3TMS,isomer #1C[Si](C)(C)OC1=CC=C2C(=C1)C=CC1=CC=CC=C1N2C(=O)N([Si](C)(C)C)[Si](C)(C)C3340.3Standard polar33892256
2-Hydroxycarbamazepine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)C=CC1=CC=CC=C1N2C(N)=O2793.6Semi standard non polar33892256
2-Hydroxycarbamazepine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(=O)N1C2=CC=CC=C2C=CC2=CC(O)=CC=C212742.1Semi standard non polar33892256
2-Hydroxycarbamazepine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=O)N1C2=CC=CC=C2C=CC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C212927.7Semi standard non polar33892256
2-Hydroxycarbamazepine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=O)N1C2=CC=CC=C2C=CC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C212868.5Standard non polar33892256
2-Hydroxycarbamazepine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=O)N1C2=CC=CC=C2C=CC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C213595.3Standard polar33892256
2-Hydroxycarbamazepine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C(=O)N1C2=CC=CC=C2C=CC2=CC(O)=CC=C21)[Si](C)(C)C(C)(C)C2999.0Semi standard non polar33892256
2-Hydroxycarbamazepine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C(=O)N1C2=CC=CC=C2C=CC2=CC(O)=CC=C21)[Si](C)(C)C(C)(C)C3037.2Standard non polar33892256
2-Hydroxycarbamazepine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C(=O)N1C2=CC=CC=C2C=CC2=CC(O)=CC=C21)[Si](C)(C)C(C)(C)C3671.3Standard polar33892256
2-Hydroxycarbamazepine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)C=CC1=CC=CC=C1N2C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3217.3Semi standard non polar33892256
2-Hydroxycarbamazepine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)C=CC1=CC=CC=C1N2C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3261.8Standard non polar33892256
2-Hydroxycarbamazepine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)C=CC1=CC=CC=C1N2C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3545.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxycarbamazepine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-0190000000-8263f1e979ef6ea456da2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxycarbamazepine GC-MS (1 TMS) - 70eV, Positivesplash10-05gi-5091000000-0215a0b081b16d1642b52017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxycarbamazepine 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 - 2-Hydroxycarbamazepine 30V, Positive-QTOFsplash10-03di-0390000000-b9b6e79d1b33c70482852021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxycarbamazepine 30V, Positive-QTOFsplash10-03di-0390000000-6793850a87f3bb81493a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxycarbamazepine 20V, Positive-QTOFsplash10-03di-0190000000-e1b2e8e65b4eb01aad662021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxycarbamazepine 50V, Positive-QTOFsplash10-066u-0910000000-8325e170e2a5137588872021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxycarbamazepine 10V, Positive-QTOFsplash10-0udi-0090000000-f5f87098f8b088288e702021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxycarbamazepine 10V, Negative-QTOFsplash10-0udi-0090000000-0d97369febab97b6cf362021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxycarbamazepine 40V, Positive-QTOFsplash10-0btc-0950000000-31b32937f1ad28de90b02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxycarbamazepine 20V, Negative-QTOFsplash10-0a4i-0090000000-b4f4fa7a9fa59ba3a6292021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxycarbamazepine 30V, Negative-QTOFsplash10-0a4i-0490000000-7a81c7a1a070bb618a032021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxycarbamazepine 55V, Positive-QTOFsplash10-000i-0090000000-e044faf46467480749922021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxycarbamazepine 35V, Positive-QTOFsplash10-01p9-0090000000-7c6bf2ed53fe38e233372021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxycarbamazepine 55V, Negative-QTOFsplash10-0udi-0090000000-229652fa3e4351b395592021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxycarbamazepine 40V, Negative-QTOFsplash10-066r-0940000000-cf2229156bcd2c5004052021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxycarbamazepine 80V, Negative-QTOFsplash10-0pb9-0090000000-0f7582a8f6ec47d653562021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxycarbamazepine 35V, Negative-QTOFsplash10-0a4i-0090000000-c77cf050a2378e5aac512021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxycarbamazepine 55V, Positive-QTOFsplash10-001i-0920000000-15101ec9e6a9769378af2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxycarbamazepine 80V, Positive-QTOFsplash10-001i-0900000000-efc7e5cf6b19e715d4772021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxycarbamazepine 55V, Negative-QTOFsplash10-0a4i-0090000000-5672bd0c599f6c1f756a2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxycarbamazepine 10V, Positive-QTOFsplash10-0udr-0090000000-01f6142623d4953745202017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxycarbamazepine 20V, Positive-QTOFsplash10-03dr-0090000000-5be2bed2e5bdad7538672017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxycarbamazepine 40V, Positive-QTOFsplash10-0bu0-0890000000-2104f95941063eb7638c2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxycarbamazepine 10V, Negative-QTOFsplash10-0pbc-5090000000-7d57df27259626e185042017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxycarbamazepine 20V, Negative-QTOFsplash10-0a4i-2090000000-1c18f58360bdfaa14dcc2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxycarbamazepine 40V, Negative-QTOFsplash10-0006-9030000000-ee9c4ce8f1381b9674d92017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxycarbamazepine 10V, Positive-QTOFsplash10-0udi-0090000000-1e4ec54a67add76c68042021-10-12Wishart 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 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