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Record Information
Version3.6
Creation Date2013-07-22 19:50:46 UTC
Update Date2017-08-15 23:27:38 UTC
HMDB IDHMDB0061144
Secondary Accession Numbers
  • HMDB61144
Metabolite Identification
Common NameHydromorphone-3-glucoside
DescriptionHydromorphone-3-glucoside 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 FormulaC23H29NO8
Average Molecular Weight447.4783
Monoisotopic Molecular Weight447.189316909
IUPAC Name(1S,5R,13R,17R)-4-methyl-10-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10-trien-14-one
Traditional Name(1S,5R,13R,17R)-4-methyl-10-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10-trien-14-one
CAS Registry NumberNot Available
SMILES
[H][C@@]12CC3=C4C(O[C@H]5C(=O)CC[C@]1([H])[C@@]45CCN2C)=C(OC1OC(CO)C(O)C(O)C1O)C=C3
InChI Identifier
InChI=1S/C23H29NO8/c1-24-7-6-23-11-3-4-13(26)21(23)32-20-14(5-2-10(16(20)23)8-12(11)24)30-22-19(29)18(28)17(27)15(9-25)31-22/h2,5,11-12,15,17-19,21-22,25,27-29H,3-4,6-9H2,1H3/t11-,12+,15?,17?,18?,19?,21-,22?,23-/m0/s1
InChI KeyLAZTZBKWNKFJLP-FBSPHTLJSA-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
  • Fatty acyl glycoside
  • Fatty acyl glycoside of mono- or disaccharide
  • Phenolic glycoside
  • Phenanthrene
  • Alkyl glycoside
  • Hexose monosaccharide
  • Glycosyl compound
  • Isoquinolone
  • O-glycosyl compound
  • Tetralin
  • Coumaran
  • Aralkylamine
  • Alkyl aryl ether
  • Fatty acyl
  • Benzenoid
  • Monosaccharide
  • Piperidine
  • Oxane
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • Ketone
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Ether
  • Acetal
  • Polyol
  • Organic oxide
  • Amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Alcohol
  • Primary alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
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 Solubility6.7 mg/mLALOGPS
logP0.19ALOGPS
logP-0.45ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)12.2ChemAxon
pKa (Strongest Basic)8.59ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area128.92 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity110.41 m3·mol-1ChemAxon
Polarizability45.24 Å3ChemAxon
Number of Rings6ChemAxon
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
PathwaysNot 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 IDDBMET00865
      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
      NuGOwiki LinkHMDB0061144
      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