Human Metabolome Database Version 3.5

Showing metabocard for (3a,5b,7a)-23-Carboxy-7-hydroxy-24-norcholan-3-yl-b-D-Glucopyranosiduronic acid (HMDB02430)

Record Information
Version 3.5
Creation Date 2006-05-22 08:17:53 -0600
Update Date 2013-02-08 17:11:54 -0700
HMDB ID HMDB02430
Secondary Accession Numbers None
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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Chenodeoxycholic acid 3-glucuronide
  2. Chenodeoxycholic acid-3-b-D-glucuronide
  3. Chenodeoxycholic acid-3-beta-delta-glucuronide
Chemical Formula C30H48O10
Average Molecular Weight 568.6961
Monoisotopic Molecular Weight 568.324747756
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 Number 58814-71-4
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 Key GDNGOAUIUTXUES-RWDHRDFGSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Steroids and Steroid Derivatives
Sub Class Steroidal 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 Parent Steroid Glucuronide Conjugates
Ontology
Status Expected 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
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.14 g/L ALOGPS
LogP 1.91 ALOGPS
LogP 2.26 ChemAxon
LogS -3.61 ALOGPS
pKa (strongest acidic) 3.44 ChemAxon
pKa (strongest basic) -0.61 ChemAxon
Hydrogen Acceptor Count 10 ChemAxon
Hydrogen Donor Count 6 ChemAxon
Polar Surface Area 173.98 A2 ChemAxon
Rotatable Bond Count 7 ChemAxon
Refractivity 141.55 ChemAxon
Polarizability 62.68 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -2 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023002
KNApSAcK ID Not Available
Chemspider ID 13628354 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB02430 Link_out
Metagene Link HMDB02430 Link_out
METLIN ID 6678 Link_out
PubChem Compound 21252299 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available

Enzymes
Name: UDP-glucuronosyltransferase 2B4
Reactions: Not Available
Gene Name: UGT2B4
Uniprot ID: P06133 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 1-4
Reactions: Not Available
Gene Name: UGT1A4
Uniprot ID: P22310 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 2B7
Reactions: Not Available
Gene Name: UGT2B7
Uniprot ID: P16662 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 1-1
Reactions: Not Available
Gene Name: UGT1A1
Uniprot ID: P22309 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 1-9
Reactions: Not Available
Gene Name: UGT1A9
Uniprot ID: O60656 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 1-6
Reactions: Not Available
Gene Name: UGT1A6
Uniprot ID: P19224 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Gastrotropin
Reactions: Not Available
Gene Name: FABP6
Uniprot ID: P51161 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Transporters
Name: Solute carrier organic anion transporter family member 1B3
Reactions: Not Available
Gene Name: SLCO1B3
Uniprot ID: Q9NPD5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Solute carrier organic anion transporter family member 1B1
Reactions: Not Available
Gene Name: SLCO1B1
Uniprot ID: Q9Y6L6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Canalicular multispecific organic anion transporter 2
Reactions: Not Available
Gene Name: ABCC3
Uniprot ID: O15438 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Bile salt export pump
Reactions: Not Available
Gene Name: ABCB11
Uniprot ID: O95342 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Ileal sodium/bile acid cotransporter
Reactions: Not Available
Gene Name: SLC10A2
Uniprot ID: Q12908 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Sodium/bile acid cotransporter
Reactions: Not Available
Gene Name: SLC10A1
Uniprot ID: Q14973 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Solute carrier organic anion transporter family member 1A2
Reactions: Not Available
Gene Name: SLCO1A2
Uniprot ID: P46721 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Solute carrier organic anion transporter family member 4A1
Reactions: Not Available
Gene Name: SLCO4A1
Uniprot ID: Q96BD0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA