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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:49:46 UTC
Update Date2019-07-23 06:35:18 UTC
HMDB IDHMDB0041954
Secondary Accession Numbers
  • HMDB41954
Metabolite Identification
Common NameNorbutorphanol
DescriptionNorcocaine belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group. These are amino acids having a (-NH2) group attached to the beta carbon atom. Norcocaine is a very strong basic compound (based on its pKa).
Structure
Data?1563863718
Synonyms
ValueSource
NorbutorphanolMeSH
Chemical FormulaC16H21NO2
Average Molecular Weight259.3434
Monoisotopic Molecular Weight259.157228921
IUPAC Name(1S,9R,10S)-17-azatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2(7),3,5-triene-4,10-diol
Traditional Name(1S,9R,10S)-17-azatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2(7),3,5-triene-4,10-diol
CAS Registry Number3792-68-5
SMILES
[H][C@@]12CC3=C(C=C(O)C=C3)[C@]3(CCCC[C@@]13O)CCN2
InChI Identifier
InChI=1S/C16H21NO2/c18-12-4-3-11-9-14-16(19)6-2-1-5-15(16,7-8-17-14)13(11)10-12/h3-4,10,14,17-19H,1-2,5-9H2/t14-,15+,16-/m1/s1
InChI KeyGJOVVPXDEXUSTC-OWCLPIDISA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenol esters
Sub ClassNot Available
Direct ParentPhenol esters
Alternative Parents
Substituents
  • Phenol ester
  • Piperidinecarboxylic acid
  • Tropane alkaloid
  • Phenoxy compound
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Piperidine
  • Pyrrolidine
  • Methyl ester
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Azacycle
  • Secondary aliphatic amine
  • Carboxylic acid derivative
  • Secondary amine
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Amine
  • Carbonyl group
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

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 Solubility0.55 g/LALOGPS
logP1.4ALOGPS
logP1.66ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)10.35ChemAxon
pKa (Strongest Basic)9.5ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area52.49 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity74.08 m³·mol⁻¹ChemAxon
Polarizability28.45 ųChemAxon
Number of Rings4ChemAxon
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, Positivesplash10-00l6-3090000000-86580687a4b5d9a2ced3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00a9-2009000000-7d2923e87bb3c217669fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ox-0090000000-c766d71bab5da602ca9fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0090000000-e3b6d582fc7e66b4225dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pb9-9130000000-8d010108007271303fc2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-6c4d47fa09baffac3e45Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-0090000000-24708a73c43829827e5dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ox-0090000000-5cb105e308f9c850395fSpectrum
Biological Properties
Cellular LocationsNot Available
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 ID27185
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNorcocaine
METLIN IDNot Available
PubChem Compound29230
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available