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Record Information
Version3.6
Creation Date2012-09-13 11:50:03 UTC
Update Date2016-02-11 03:55:39 UTC
HMDB IDHMDB41959
Secondary Accession NumbersNone
Metabolite Identification
Common NameNormorphine
DescriptionNormorphine is an opiate analogue, the N-demethylated derivative of morphine, that was first described in the 1950s when a large group of N-substituted morphine analogues were characterized for activity.
Structure
Thumb
Synonyms
ValueSource
(-)-NormorphineHMDB
4,5-Epoxy-3,6-dihydroxymorphin-7-eneHMDB
7,8-didehydro-4,5alpha-Epoxy-morphinan-3,6alpha-diolHMDB
DemethylmorphineHMDB
DesmethylmorphineHMDB
N-NormorphineHMDB
Chemical FormulaC16H17NO3
Average Molecular Weight271.3111
Monoisotopic Molecular Weight271.120843415
IUPAC Name12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10,15-tetraene-10,14-diol
Traditional Name12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10,15-tetraene-10,14-diol
CAS Registry Number466-97-7
SMILES
OC1C=CC2C3CC4=C5C(OC1C25CCN3)=C(O)C=C4
InChI Identifier
InChI=1S/C16H17NO3/c18-11-3-1-8-7-10-9-2-4-12(19)15-16(9,5-6-17-10)13(8)14(11)20-15/h1-4,9-10,12,15,17-19H,5-7H2
InChI KeyInChIKey=ONBWJWYUHXVEJS-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Benzylisoquinoline
  • Phenanthrene
  • Tetralin
  • Benzofuran
  • Aralkylamine
  • Alkyl aryl ether
  • Benzenoid
  • Piperidine
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Ether
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
  • Endogenous
Biofunction
  • Nutrient
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point273 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-0.17Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.19 mg/mLALOGPS
logP0.4ALOGPS
logP0.26ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)10.47ChemAxon
pKa (Strongest Basic)9.77ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area61.72 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity74.83 m3·mol-1ChemAxon
Polarizability28.37 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB LinkKEGG Link
Morphine Metabolism PathwaySMP00622Not Available
Morphine PathwaySMP00406Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00649
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID380506
KEGG Compound IDC11785
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Linknormorphine
NuGOwiki LinkHMDB41959
Metagene LinkHMDB41959
METLIN IDNot Available
PubChem Compound430245
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available