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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:57 UTC
Update Date2018-05-20 20:34:58 UTC
HMDB IDHMDB0002579
Secondary Accession Numbers
  • HMDB02579
Metabolite Identification
Common NameGlycochenodeoxycholic acid 3-glucuronide
DescriptionGlycochenodeoxycholic acid (GCDC)induced the mitochondrial permeability transition (MPT) in a dose-dependent manner, which was inhibited by cyclosporin A, alpha-tocopherol, beta-carotene and idebenone. GCDC stimulated reactive oxygen species generation and release of cytochrome c and apoptosis-inducing factor, which were significantly inhibited by the antioxidants, cyclosporin A, and tauroursodeoxycholic acid. mitochondrial pathways of cell death are stimulated in human hepatic mitochondria exposed to GCDC consistent with the role of mitochondrial dysfunction in the pathogenesis of cholestatic liver injury. (16056106).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC32H51NO11
Average Molecular Weight625.7474
Monoisotopic Molecular Weight625.346211479
IUPAC Name(2S,3S,4S,5R,6R)-6-{[(1S,2S,5R,7R,9R,10R,11S,15R)-14-[(2R)-4-[(carboxymethyl)carbamoyl]butan-2-yl]-9-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6R)-6-{[(1S,2S,5R,7R,9R,10R,11S,15R)-14-[(2R)-4-(carboxymethylcarbamoyl)butan-2-yl]-9-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Registry Number79254-98-1
SMILES
[H][C@@]12CCC([C@H](C)CCC(=O)NCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)C[C@]2([H])C[C@@H](CC[C@]12C)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O
InChI Identifier
InChI=1S/C32H51NO11/c1-15(4-7-22(35)33-14-23(36)37)18-5-6-19-24-20(9-11-32(18,19)3)31(2)10-8-17(12-16(31)13-21(24)34)43-30-27(40)25(38)26(39)28(44-30)29(41)42/h15-21,24-28,30,34,38-40H,4-14H2,1-3H3,(H,33,35)(H,36,37)(H,41,42)/t15-,16+,17-,18?,19+,20+,21-,24+,25+,26+,27-,28+,30-,31+,32-/m1/s1
InChI KeyABFZMYIIUREPLL-ZWDGUQLWSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as steroid glucuronide conjugates. These are sterol lipids containing a glucuronide moiety linked to the steroid skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroidal glycosides
Direct ParentSteroid glucuronide conjugates
Alternative Parents
Substituents
  • Glycinated bile acid
  • Steroid-glucuronide-skeleton
  • Monohydroxy bile acid, alcohol, or derivatives
  • Hydroxy bile acid, alcohol, or derivatives
  • Bile acid, alcohol, or derivatives
  • Hydroxysteroid
  • 7-hydroxysteroid
  • O-glucuronide
  • 1-o-glucuronide
  • Glucuronic acid or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Hexose monosaccharide
  • O-glycosyl compound
  • Glycosyl compound
  • Alpha-amino acid or derivatives
  • Beta-hydroxy acid
  • Dicarboxylic acid or derivatives
  • Fatty amide
  • Fatty acyl
  • Hydroxy acid
  • Monosaccharide
  • N-acyl-amine
  • Pyran
  • Oxane
  • Cyclic alcohol
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Secondary alcohol
  • Organoheterocyclic compound
  • Polyol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Acetal
  • Oxacycle
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

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 Solubility0.072 g/LALOGPS
logP1.48ALOGPS
logP1.16ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)3.29ChemAxon
pKa (Strongest Basic)-0.61ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area203.08 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity154.36 m³·mol⁻¹ChemAxon
Polarizability67.52 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
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, Positivesplash10-053i-7273596000-74e7ecdd4f80883e26beView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05fr-9000825000-c3ec8785d86612047bbdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9000300000-cc5c8650d38bca1e06bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9001100000-4c5ac1ea22c9ebbcb5e7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-008a-2200978000-af0e899e0d12ebe06521View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001j-2200921000-5149f175635371b9f104View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006t-9503800000-8be6e9bd043006b7f60bView in MoNA
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
      Phenol Explorer Compound IDNot Available
      FoodDB IDFDB023027
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDC03033
      BioCyc IDBeta-D-Glucuronides
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN ID6715
      PubChem Compound53477753
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General References
      1. Goto J: [Chromatographic determination of bile acids in biological fluids with sensitive and selective detection]. Yakugaku Zasshi. 1990 Nov;110(11):807-21. [PubMed:2082011 ]

      Only showing the first 10 proteins. There are 18 proteins in total.

      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
      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
      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
      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
      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
      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
      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
      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
      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
      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

      Only showing the first 10 proteins. There are 18 proteins in total.