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Record Information
Version3.6
Creation Date2012-09-13 11:50:03 UTC
Update Date2017-03-02 21:45:51 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
Normorphine hydrochlorideMeSH
Normorphine sulfamateMeSH
Normorphine perchlorateMeSH
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 KeyONBWJWYUHXVEJS-UHFFFAOYSA-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
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Piperidine
  • Benzenoid
  • Secondary alcohol
  • Secondary aliphatic amine
  • Ether
  • Oxacycle
  • Secondary amine
  • Azacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Amine
  • Alcohol
  • Organic nitrogen compound
  • 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 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 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