Record Information
Version3.6
Creation Date2006-05-22 14:17:53 UTC
Update Date2013-02-09 00:11:54 UTC
HMDB IDHMDB02430
Secondary Accession NumbersNone
Metabolite Identification
Common Name(3a,5b,7a)-23-Carboxy-7-hydroxy-24-norcholan-3-yl-b-D-Glucopyranosiduronic acid
Description(3a,5b,7a)-23-carboxy-7-hydroxy-24-norcholan-3-yl-b-D-Glucopyranosiduronic acid is a natural human metabolite of Chenodeoxycholic acid generated in the liver by UDP glucuonyltransferase. Glucuronidation is used to assist in the excretion of toxic substances, drugs or other substances that cannot be used as an energy source. Glucuronic acid is attached via a glycosidic bond to the substance, and the resulting glucuronide, which has a much higher water solubility than the original substance, is eventually excreted by the kidneys.
Structure
Thumb
Synonyms
  1. Chenodeoxycholic acid 3-glucuronide
  2. Chenodeoxycholic acid-3-b-D-glucuronide
  3. Chenodeoxycholic acid-3-beta-delta-glucuronide
Chemical FormulaC30H48O10
Average Molecular Weight568.6961
Monoisotopic Molecular Weight568.324747756
IUPAC Name(2S,3S,4S,5R)-6-{[(1S,2S,5R,7R,9R,10R,11S,14R,15R)-14-[(2R)-4-carboxybutan-2-yl]-9-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional IUPAC Name(2S,3S,4S,5R)-6-{[(1S,2S,5R,7R,9R,10R,11S,14R,15R)-14-[(2R)-4-carboxybutan-2-yl]-9-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Registry Number58814-71-4
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)OC1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O)[C@H](C)CCC(O)=O
InChI Identifier
InChI=1S/C30H48O10/c1-14(4-7-21(32)33)17-5-6-18-22-19(9-11-30(17,18)3)29(2)10-8-16(12-15(29)13-20(22)31)39-28-25(36)23(34)24(35)26(40-28)27(37)38/h14-20,22-26,28,31,34-36H,4-13H2,1-3H3,(H,32,33)(H,37,38)/t14-,15+,16-,17-,18+,19+,20-,22+,23+,24+,25-,26+,28?,29+,30-/m1/s1
InChI KeyGDNGOAUIUTXUES-RWDHRDFGSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassSteroids and Steroid Derivatives
Sub ClassSteroidal Glycosides
Other Descriptors
  • Aliphatic Heteropolycyclic Compounds
  • Steroids and Steroid Derivatives
Substituents
  • 1,2 Diol
  • 7 Hydroxy Steroid
  • Acetal
  • Beta Hydroxy Acid
  • Bicyclohexane
  • Bile Acid, Alcohol, Or Derivative
  • Carboxylic Acid
  • Cyclic Alcohol
  • Cyclohexane
  • Decaline
  • Dicarboxylic Acid Derivative
  • Glucuronic Acid Or Derivative
  • Glucuronide
  • Glycosyl Compound
  • Hexose Monosaccharide
  • Hydroxy Bile Acid, Alcohol, Or Derivative
  • Monohydroxy Bile Acid, Alcohol, Or Derivative
  • O Glycosyl Compound
  • Oxane
  • Saccharide
  • Secondary Alcohol
  • Sesterterpene
  • Sugar Acid
  • Terpene Glycoside
Direct ParentSteroid Glucuronide Conjugates
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fat solubilization and Waste products
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
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 solubility0.14 g/LALOGPS
logP1.91ALOGPS
logP2.26ChemAxon
logS-3.6ALOGPS
pKa (strongest acidic)3.44ChemAxon
pKa (strongest basic)-0.61ChemAxon
physiological charge-2ChemAxon
hydrogen acceptor count10ChemAxon
hydrogen donor count6ChemAxon
polar surface area173.98ChemAxon
rotatable bond count7ChemAxon
refractivity141.55ChemAxon
polarizability62.68ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023002
KNApSAcK IDNot Available
Chemspider ID13628354
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB02430
Metagene LinkHMDB02430
METLIN ID6678
PubChem Compound21252299
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Gene Name:
UGT2B4
Uniprot ID:
P06133
Gene Name:
UGT1A4
Uniprot ID:
P22310
Gene Name:
UGT2B7
Uniprot ID:
P16662
Gene Name:
UGT1A1
Uniprot ID:
P22309
Gene Name:
UGT1A9
Uniprot ID:
O60656
Gene Name:
UGT1A6
Uniprot ID:
P19224
Gene Name:
FABP6
Uniprot ID:
P51161

Transporters

Gene Name:
ABCB11
Uniprot ID:
O95342
Gene Name:
SLC10A2
Uniprot ID:
Q12908
Gene Name:
SLC10A1
Uniprot ID:
Q14973