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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-06-12 17:33:29 UTC
Update Date2019-07-23 07:14:34 UTC
HMDB IDHMDB0060548
Secondary Accession Numbers
  • HMDB60548
Metabolite Identification
Common NameDihydromorphine
DescriptionDihydromorphine, also known as paramorphan or 6α-hydromorphol, 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. Dihydromorphine is a very strong basic compound (based on its pKa). In humans, dihydromorphine is involved in dihydromorphine action pathway. A semisynthetic analgesic used in the study of narcotic receptors. The 7,8-double bond in morphine is reduced to a single bond to get dihydromorphine. Dihydromorphine is a semi-synthetic opioid structurally related to and derived from morphine. Dihydromorphine is a metabolite of Hydromorphone. It has abuse potential.
Structure
Data?1563866074
Synonyms
ValueSource
ParamorphanHMDB
ParamorfanHMDB
(5alpha,6alpha)-4,5-Epoxy-17-methylmorphinan-3,6-diolHMDB
(5Α,6α)-4,5-epoxy-17-methylmorphinan-3,6-diolHMDB
6alpha-7,8-DihydromorphineHMDB
6alpha-HydromorpholHMDB
6Α-7,8-dihydromorphineHMDB
6Α-hydromorpholHMDB
7,8-DihydromorphineHMDB
DHMHMDB
HydromorphineHMDB
alpha-DihydromorphineHMDB
Α-dihydromorphineHMDB
DihydromorphineHMDB
Chemical FormulaC17H21NO3
Average Molecular Weight287.3535
Monoisotopic Molecular Weight287.152143543
IUPAC Name(1S,5R,13R,14S,17R)-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10-triene-10,14-diol
Traditional Name(1S,5R,13R,14S,17R)-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10-triene-10,14-diol
CAS Registry Number509-60-4
SMILES
[H][C@@]12OC3=C4C(C[C@@]5([H])N(C)CC[C@@]14[C@@]5([H])CC[C@@H]2O)=CC=C3O
InChI Identifier
InChI=1S/C17H21NO3/c1-18-7-6-17-10-3-5-13(20)16(17)21-15-12(19)4-2-9(14(15)17)8-11(10)18/h2,4,10-11,13,16,19-20H,3,5-8H2,1H3/t10-,11+,13-,16-,17-/m0/s1
InChI KeyIJVCSMSMFSCRME-KBQPJGBKSA-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
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Piperidine
  • Benzenoid
  • Cyclic alcohol
  • Secondary alcohol
  • Tertiary aliphatic amine
  • Tertiary amine
  • Ether
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

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 Solubility1.82 g/LALOGPS
logP1.26ALOGPS
logP1.08ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)10.29ChemAxon
pKa (Strongest Basic)9.24ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area52.93 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity79.16 m³·mol⁻¹ChemAxon
Polarizability30.68 ųChemAxon
Number of Rings5ChemAxon
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, Positivesplash10-0006-2090000000-64b6783f4c86622fea8fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01di-6309700000-61de6f13f6659db9e236Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-504a9b2ff60a0d7f4411Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0090000000-c3e1bdcbec4cf28275c3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kfx-4090000000-27a1656cb074b87c4b26Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-6acbb360a4571844e9a1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-6757484a2717da0640a0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00bc-0290000000-a1dc3f7fe7b08229191dSpectrum
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 IDDB01565
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC11782
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDihydromorphine
METLIN IDNot Available
PubChem Compound5359421
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available