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Record Information
Version4.0
Creation Date2012-09-13 11:48:50 UTC
Update Date2017-10-23 19:10:15 UTC
HMDB IDHMDB0041936
Secondary Accession Numbers
  • HMDB41936
Metabolite Identification
Common NameMorphine-3-glucuronide
DescriptionMorphine-3-glucuronide belongs to the family of 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.
Structure
Thumb
Synonyms
ValueSource
Morphine 3-glucuronide(minor)ChEMBL
Morphine-3beta-D-glucuronideMeSH
Chemical FormulaC23H27NO9
Average Molecular Weight461.4618
Monoisotopic Molecular Weight461.168581467
IUPAC Name(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(1S,5R,13R,14S,17R)-14-hydroxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10,15-tetraen-10-yl]oxy}oxane-2-carboxylic acid
Traditional Namemorphine-3-glucuronide
CAS Registry Number20290-09-9
SMILES
[H][C@@]12CC3=C4C(O[C@H]5[C@@H](O)C=C[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=1S/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/h2-5,10-12,15-17,19-20,22,25-28H,6-8H2,1H3,(H,29,30)/t10-,11+,12-,15-,16-,17+,19-,20-,22+,23-/m0/s1
InChI KeyWAEXKFONHRHFBZ-ZXDZBKESSA-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
  • 1-o-glucuronide
  • O-glucuronide
  • Phenanthrene
  • Glucuronic acid or derivatives
  • Alkyl glycoside
  • Glycosyl compound
  • O-glycosyl compound
  • Tetralin
  • Coumaran
  • Alkyl aryl ether
  • Beta-hydroxy acid
  • Aralkylamine
  • Pyran
  • Piperidine
  • Oxane
  • Benzenoid
  • Fatty acyl
  • Hydroxy acid
  • Monosaccharide
  • Tertiary amine
  • Secondary alcohol
  • Amino acid or derivatives
  • Amino acid
  • Tertiary aliphatic amine
  • Organoheterocyclic compound
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Acetal
  • Polyol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • Organooxygen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Carbonyl group
  • Alcohol
  • Organic oxide
  • Amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility9.06 g/LALOGPS
logP-0.63ALOGPS
logP-3.5ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)2.67ChemAxon
pKa (Strongest Basic)9.17ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area149.15 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity112.13 m³·mol⁻¹ChemAxon
Polarizability45.51 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, Positivesplash10-052f-9015500000-6efd8a07efbced2ab8d5View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-03di-5312039000-4e3af59a311a1a8d4ff3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01pc-0090700000-e7fd49d19d854ee34dafView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0090000000-6e5563d713276370c128View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01bi-2190000000-6b6a368a1d84af573a8cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03e9-2341900000-9ae8b4daaa0b2d5ff3faView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1290200000-3a05bfbed3f84a1ef6aaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-3190000000-22d2ab5a61d00c8fce61View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB/PathwhizKEGG
Morphine Metabolism PathwayPw000598Pw000598 greyscalePw000598 simpleNot Available
Morphine PathwayPw000412Pw000412 greyscalePw000412 simpleNot Available
Displaying all 2 entries
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 IDDBMET00462
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider ID4588593
      KEGG Compound IDC16643
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia Linkmorphine-3-glucuronide
      METLIN IDNot Available
      PubChem Compound5484731
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available

      Enzymes

      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme has glucuronidating capacity with steroid substrates such as 5-beta-androstane 3-alpha,17-beta-diol, estradiol, ADT, eugenol and bile acids. Only isoform 1 seems to be active.
      Gene Name:
      UGT2B28
      Uniprot ID:
      Q9BY64
      Molecular weight:
      38742.9
      Reactions
      Morphine + Uridine diphosphate glucuronic acid → Morphine-3-glucuronide + Uridine 5'-diphosphatedetails
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as estriol, 4-hydroxyestrone and 2-hydroxyestriol) and xenobiotics (such as 4-methylumbelliferone, 1-naphthol, 4-nitrophenol, 2-aminophenol, 4-hydroxybiphenyl and menthol). It is capable of 6 alpha-hydroxyglucuronidation of hyodeoxycholic acid.
      Gene Name:
      UGT2B4
      Uniprot ID:
      P06133
      Molecular weight:
      60512.035
      Reactions
      Morphine + Uridine diphosphate glucuronic acid → Morphine-3-glucuronide + Uridine 5'-diphosphatedetails
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate.
      Gene Name:
      UGT1A4
      Uniprot ID:
      P22310
      Molecular weight:
      60024.535
      Reactions
      Morphine + Uridine diphosphate glucuronic acid → Morphine-3-glucuronide + Uridine 5'-diphosphatedetails
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
      Gene Name:
      UGT2B10
      Uniprot ID:
      P36537
      Molecular weight:
      60773.485
      Reactions
      Morphine + Uridine diphosphate glucuronic acid → Morphine-3-glucuronide + Uridine 5'-diphosphatedetails
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
      Gene Name:
      UGT2B7
      Uniprot ID:
      P16662
      Molecular weight:
      60720.15
      Reactions
      Morphine + Uridine diphosphate glucuronic acid → Morphine-3-glucuronide + Uridine 5'-diphosphatedetails
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme displays activity toward several classes of xenobiotic substrates, including simple phenolic compounds, 7-hydroxylated coumarins, flavonoids, anthraquinones, and certain drugs and their hydroxylated metabolites. It also catalyzes the glucuronidation of endogenous estrogens and androgens.
      Gene Name:
      UGT2B15
      Uniprot ID:
      P54855
      Molecular weight:
      61035.815
      Reactions
      Morphine + Uridine diphosphate glucuronic acid → Morphine-3-glucuronide + Uridine 5'-diphosphatedetails
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDP-glucuronosyltransferases catalyze phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase water solubility and enhance excretion. They are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Active on odorants and seems to be involved in olfaction; it could help clear lipophilic odorant molecules from the sensory epithelium.
      Gene Name:
      UGT2A1
      Uniprot ID:
      Q9Y4X1
      Molecular weight:
      60771.605
      Reactions
      Morphine + Uridine diphosphate glucuronic acid → Morphine-3-glucuronide + Uridine 5'-diphosphatedetails
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
      Gene Name:
      UGT1A1
      Uniprot ID:
      P22309
      Molecular weight:
      59590.91
      Reactions
      Morphine + Uridine diphosphate glucuronic acid → Morphine-3-glucuronide + Uridine 5'-diphosphatedetails
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
      Gene Name:
      UGT1A9
      Uniprot ID:
      O60656
      Molecular weight:
      59940.495
      Reactions
      Morphine + Uridine diphosphate glucuronic acid → Morphine-3-glucuronide + Uridine 5'-diphosphatedetails
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
      Gene Name:
      UGT1A8
      Uniprot ID:
      Q9HAW9
      Molecular weight:
      59741.035
      Reactions
      Morphine + Uridine diphosphate glucuronic acid → Morphine-3-glucuronide + Uridine 5'-diphosphatedetails
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
      Gene Name:
      UGT1A3
      Uniprot ID:
      P35503
      Molecular weight:
      60337.835
      Reactions
      Morphine + Uridine diphosphate glucuronic acid → Morphine-3-glucuronide + Uridine 5'-diphosphatedetails
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
      Gene Name:
      UGT1A10
      Uniprot ID:
      Q9HAW8
      Molecular weight:
      59809.075
      Reactions
      Morphine + Uridine diphosphate glucuronic acid → Morphine-3-glucuronide + Uridine 5'-diphosphatedetails
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. The major substrates of this isozyme are eugenol > 4-methylumbelliferone > dihydrotestosterone (DHT) > androstane-3-alpha,17-beta-diol (3-alpha-diol) > testosterone > androsterone (ADT).
      Gene Name:
      UGT2B17
      Uniprot ID:
      O75795
      Molecular weight:
      61094.915
      Reactions
      Morphine + Uridine diphosphate glucuronic acid → Morphine-3-glucuronide + Uridine 5'-diphosphatedetails
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
      Gene Name:
      UGT1A6
      Uniprot ID:
      P19224
      Molecular weight:
      60750.215
      Reactions
      Morphine + Uridine diphosphate glucuronic acid → Morphine-3-glucuronide + Uridine 5'-diphosphatedetails
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
      Gene Name:
      UGT1A5
      Uniprot ID:
      P35504
      Molecular weight:
      60070.565
      Reactions
      Morphine + Uridine diphosphate glucuronic acid → Morphine-3-glucuronide + Uridine 5'-diphosphatedetails
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
      Gene Name:
      UGT2B11
      Uniprot ID:
      O75310
      Molecular weight:
      61037.8
      Reactions
      Morphine + Uridine diphosphate glucuronic acid → Morphine-3-glucuronide + Uridine 5'-diphosphatedetails
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
      Gene Name:
      UGT1A7
      Uniprot ID:
      Q9HAW7
      Molecular weight:
      59818.315
      Reactions
      Morphine + Uridine diphosphate glucuronic acid → Morphine-3-glucuronide + Uridine 5'-diphosphatedetails
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDP-glucuronosyltransferases catalyze phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase water solubility and enhance excretion. They are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds (By similarity).
      Gene Name:
      UGT2A3
      Uniprot ID:
      Q6UWM9
      Molecular weight:
      60253.94
      Reactions
      Morphine + Uridine diphosphate glucuronic acid → Morphine-3-glucuronide + Uridine 5'-diphosphatedetails