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Bovine Metabolome Database



Showing metabocard for 3b,12a-Dihydroxy-5a-cholanoic acid (BMDB00348)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-05-05 20:57:53
Accession Number BMDB00348
Common Name 3b,12a-Dihydroxy-5a-cholanoic acid
Description A bile acid. Bile acids are steroid acids found predominantly in bile of mammals. The distinction between different bile acids is minute, depends only on presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g., membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues.
Synonyms
  1. 3-epi-deoxycholate
  2. 3-epi-deoxycholic acid
  3. 3b,12a-Dihydroxy-5a-cholanoate
  4. 3b,12a-Dihydroxy-5a-cholanoic acid
  5. 3b,12a-dihydroxy-(5a)-cholan-24-oate
  6. 3b,12a-dihydroxy-(5a)-cholan-24-oic acid
Chemical IUPAC Name Not Available
Chemical Formula C24H40O4
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Cholesterols and derivatives
Class
  • Bile Acids
Sub Class
  • Dihydroxy bile acids
Family
  • Mammalian_Metabolite
Species
  • secondary alcohol; carboxylic acid
Biofunction
  • Fat solubilization and Waste products
Application
Source
  • Endogenous
Average Molecular Weight 392.572
Monoisotopic Molecular Weight 392.292664
Isomeric SMILES C[C@H](CCC(O)=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](O)CC[C@]4(C)[C@H]3C[C@H](O)[C@]12C
Canonical SMILES CC(CCC(O)=O)C1CCC2C3CCC4CC(O)CCC4(C)C3CC(O)C12C
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
METLIN ID 5337 Link Image
PubChem Compound Not Available
PubChem Substance Not Available
ChEBI ID Not Available
CAS Registry Number 2569-04-2
InChI Identifier InChI=1/C24H40O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16+,17+,18-,19+,20+,21+,23+,24-/m1/s1
Synthesis Reference Iqbal, Mohammed N.; Elliott, William H. Bile acids. LXXIX. Synthesis and reduction of 1,4-dien-3-ones of various bile acids. Steroids (1989), 53(3-5), 413-25.
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 0.0173 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -1
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 3.30 [Predicted by ALOGPS] Calculated using ALOGPS
Material Safety Data Sheet (MSDS) Not Available
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
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Predicted 13C NMR Spectrum Show Image
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Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location Not Available
Biofluid Location Not Available
Tissue Location
Tissue References
Gall Bladder
Intestine
Kidney
Liver
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Pathway Names Not Available
HMDB Pathways Not Available
KEGG Pathways Not Available
SimCell Pathways Not Available
General References Not Available