Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:07:51 UTC
Update Date2021-09-14 15:19:57 UTC
HMDB IDHMDB0060929
Secondary Accession Numbers
  • HMDB60929
Metabolite Identification
Common NameDihydroisomorphine
DescriptionDihydroisomorphine is a metabolite of hydromorphone. Hydromorphone, a more common synonym for dihydromorphinone, commonly a hydrochloride (brand names Palladone, Dilaudid, and numerous others) is a very potent centrally acting analgesic drug of the opioid class. It is a derivative of morphine, to be specific, a hydrogenated ketone thereof and, therefore, a semi-synthetic drug. It is, in medical terms, an opioid analgesic and, in legal terms, a narcotic. (Wikipedia)
Structure
Data?1563866124
Synonyms
ValueSource
(5alpha,6beta)-4,5-Epoxy-17-methylmorphinan-3,6-diolHMDB
(5Α,6β)-4,5-epoxy-17-methylmorphinan-3,6-diolHMDB
6beta-HydromorpholHMDB
6Β-hydromorpholHMDB
Dihydro-alpha-isomorphineHMDB
Dihydro-α-isomorphineHMDB
DihydroisomorphineHMDB
Chemical FormulaC17H21NO3
Average Molecular Weight287.359
Monoisotopic Molecular Weight287.15214354
IUPAC Name(1S,5R,13R,14R,17R)-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7,9,11(18)-triene-10,14-diol
Traditional Name(1S,5R,13R,14R,17R)-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7,9,11(18)-triene-10,14-diol
CAS Registry Number26626-12-0
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-NOSXKOESSA-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 DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
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 Solubility3.53 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
Polarizability30.62 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-208.27830932474
DeepCCS[M+Na]+184.30230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Dihydroisomorphine[H][C@@]12OC3=C4C(C[C@@]5([H])N(C)CC[C@@]14[C@@]5([H])CC[C@H]2O)=CC=C3O3932.8Standard polar33892256
Dihydroisomorphine[H][C@@]12OC3=C4C(C[C@@]5([H])N(C)CC[C@@]14[C@@]5([H])CC[C@H]2O)=CC=C3O2334.6Standard non polar33892256
Dihydroisomorphine[H][C@@]12OC3=C4C(C[C@@]5([H])N(C)CC[C@@]14[C@@]5([H])CC[C@H]2O)=CC=C3O2475.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Dihydroisomorphine,1TMS,isomer #1CN1CC[C@]23C4=C5C=CC(O)=C4O[C@H]2[C@H](O[Si](C)(C)C)CC[C@H]3[C@H]1C52414.1Semi standard non polar33892256
Dihydroisomorphine,1TMS,isomer #2CN1CC[C@]23C4=C5C=CC(O[Si](C)(C)C)=C4O[C@H]2[C@H](O)CC[C@H]3[C@H]1C52472.6Semi standard non polar33892256
Dihydroisomorphine,2TMS,isomer #1CN1CC[C@]23C4=C5C=CC(O[Si](C)(C)C)=C4O[C@H]2[C@H](O[Si](C)(C)C)CC[C@H]3[C@H]1C52480.4Semi standard non polar33892256
Dihydroisomorphine,1TBDMS,isomer #1CN1CC[C@]23C4=C5C=CC(O)=C4O[C@H]2[C@H](O[Si](C)(C)C(C)(C)C)CC[C@H]3[C@H]1C52677.9Semi standard non polar33892256
Dihydroisomorphine,1TBDMS,isomer #2CN1CC[C@]23C4=C5C=CC(O[Si](C)(C)C(C)(C)C)=C4O[C@H]2[C@H](O)CC[C@H]3[C@H]1C52744.8Semi standard non polar33892256
Dihydroisomorphine,2TBDMS,isomer #1CN1CC[C@]23C4=C5C=CC(O[Si](C)(C)C(C)(C)C)=C4O[C@H]2[C@H](O[Si](C)(C)C(C)(C)C)CC[C@H]3[C@H]1C52926.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Dihydroisomorphine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydroisomorphine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroisomorphine 10V, Positive-QTOFsplash10-000i-0090000000-8e23f9bfe8905382513a2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroisomorphine 20V, Positive-QTOFsplash10-000i-0090000000-1ec5d5a94424722655522021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroisomorphine 40V, Positive-QTOFsplash10-000i-0090000000-ab4dccbaff63f6897f592021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroisomorphine 10V, Negative-QTOFsplash10-000i-0090000000-32affc6af32f5da1d2572021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroisomorphine 20V, Negative-QTOFsplash10-000i-0090000000-32affc6af32f5da1d2572021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroisomorphine 40V, Negative-QTOFsplash10-000i-0090000000-842b3a0fd7fd18ba1b062021-10-12Wishart LabView Spectrum
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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID7990198
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9814448
PDB IDNot Available
ChEBI IDNot Available
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