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Record Information
Version3.6
Creation Date2013-07-09 16:07:56 UTC
Update Date2016-02-11 08:15:36 UTC
HMDB IDHMDB60930
Secondary Accession NumbersNone
Metabolite Identification
Common NameHydromorphone 3-beta-O-glucuronide
DescriptionHydromorphone 3-beta-O-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 FormulaC23H27NO9
Average Molecular Weight461.4618
Monoisotopic Molecular Weight461.168581467
IUPAC Name(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(1R,5S,13S,17S)-4-methyl-14-oxo-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10-trien-10-yl]oxy}oxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(1R,5S,13S,17S)-4-methyl-14-oxo-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10-trien-10-yl]oxy}oxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
[H][C@]12CC3=C4C(O[C@@H]5C(=O)CC[C@H]1[C@]45CCN2C)=C(O[C@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O)C=C3
InChI Identifier
InChI=1/C23H27NO9/c1-24-7-6-23-10-3-4-12(25)20(23)32-18-13(5-2-9(14(18)23)8-11(10)24)31-22-17(28)15(26)16(27)19(33-22)21(29)30/h2,5,10-11,15-17,19-20,22,26-28H,3-4,6-8H2,1H3,(H,29,30)/t10-,11+,15+,16+,17-,19+,20-,22+,23-/s2
InChI KeyInChIKey=VLSHIBYUEOPPRX-MIPBTCAHNA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Fatty acyl glycoside
  • Benzylisoquinoline
  • Phenolic glycoside
  • Phenanthrene
  • O-glucuronide
  • 1-o-glucuronide
  • Glucuronic acid or derivatives
  • Alkyl glycoside
  • O-glycosyl compound
  • Isoquinolone
  • Glycosyl compound
  • Tetralin
  • Pyran carboxylic acid
  • Pyran carboxylic acid or derivatives
  • Benzofuran
  • Aralkylamine
  • Cyclohexanone
  • Beta-hydroxy acid
  • Alkyl aryl ether
  • Fatty acyl
  • Benzenoid
  • Pyran
  • Piperidine
  • Oxane
  • Monosaccharide
  • Hydroxy acid
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • Polyol
  • Ketone
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Acetal
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • 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 Solubility10.5 mg/mLALOGPS
logP-0.28ALOGPS
logP-2.9ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)2.68ChemAxon
pKa (Strongest Basic)8.59ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area145.99 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity110.27 m3·mol-1ChemAxon
Polarizability45.69 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 QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00180
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 LinkHMDB60930
Metagene LinkHMDB60930
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