You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-22 19:50:16 UTC
Update Date2017-10-23 19:15:53 UTC
HMDB IDHMDB0061137
Secondary Accession Numbers
  • HMDB61137
Metabolite Identification
Common NameDihydroisomorphine-6-glucuronide
DescriptionDihydroisomorphine-6-glucuronide 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
Thumb
SynonymsNot Available
Chemical FormulaC23H29NO9
Average Molecular Weight463.4777
Monoisotopic Molecular Weight463.184231531
IUPAC Name(2R,3R,4R,5S,6S)-3,4,5-trihydroxy-6-{[(1S,5R,13R,14R,17R)-10-hydroxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10-trien-14-yl]oxy}oxane-2-carboxylic acid
Traditional Name(2R,3R,4R,5S,6S)-3,4,5-trihydroxy-6-{[(1S,5R,13R,14R,17R)-10-hydroxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10-trien-14-yl]oxy}oxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
[H][C@@]12CC3=C4C(O[C@H]5[C@@H](CC[C@]1([H])[C@@]45CCN2C)O[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)C(O)=O)=C(O)C=C3
InChI Identifier
InChI=1S/C23H29NO9/c1-24-7-6-23-10-3-5-13(31-22-17(28)15(26)16(27)19(33-22)21(29)30)20(23)32-18-12(25)4-2-9(14(18)23)8-11(10)24/h2,4,10-11,13,15-17,19-20,22,25-28H,3,5-8H2,1H3,(H,29,30)/t10-,11+,13+,15+,16+,17-,19+,20-,22-,23-/m0/s1
InChI KeyDSUSABDLTYJUKQ-NCRPEHEWSA-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
  • 1-o-glucuronide
  • O-glucuronide
  • Phenanthrene
  • Glucuronic acid or derivatives
  • Glycosyl compound
  • O-glycosyl compound
  • Tetralin
  • Coumaran
  • Alkyl aryl ether
  • Beta-hydroxy acid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Benzenoid
  • Hydroxy acid
  • Monosaccharide
  • Oxane
  • Piperidine
  • Pyran
  • Amino acid or derivatives
  • Tertiary aliphatic amine
  • Tertiary amine
  • Amino acid
  • Secondary alcohol
  • Azacycle
  • Oxacycle
  • Polyol
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Acetal
  • Ether
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Amine
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Organopnictogen compound
  • Organic oxide
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

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 Solubility11.9 g/LALOGPS
logP-0.34ALOGPS
logP-2.8ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)2.91ChemAxon
pKa (Strongest Basic)9.24ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area149.15 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity111.44 m³·mol⁻¹ChemAxon
Polarizability46.27 ųChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6v-9104200000-d81d02ad24c2bd8b7216View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-03xr-5411139000-31582dd780fecfaa5e56View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01pa-0090700000-52d292ec3d55797c2758View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0090000000-9e8fe7885227e4fdf6eeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05g0-1190000000-479c12590db5e423edfaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03y0-1240900000-862f2884b82331af7af1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1290200000-8ac7eb9cdee8ccb8ab35View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-3190000000-8218a2839fc385fb51f4View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
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 IDDBMET00838
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDNot Available
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem CompoundNot Available
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available