FComEx: 3a,6b,7b-Trihydroxy-5b-cholanoic acid (PC000849)

Record Information

Version

1.0

Creation date

2015-10-09 22:33:05 UTC

Update date

2017-01-19 02:36:39 UTC

FoodComEx ID

PC000849

FoodDB Record

FDB022031

Chemical Information

Name

3a,6b,7b-Trihydroxy-5b-cholanoic acid

Description

3a,6b,7b-Trihydroxy-5b-cholanoic acid is a bile acid found in urine exhibiting a complex modification pattern, including free, glyco- and sulfoconjugated forms (PMID 3834660). 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. (PMID: 11316487, 16037564, 12576301, 11907135) [HMDB]

CAS Number

2393-59-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
3a,6b,7b-Trihydroxy-5b-cholan-24-oate	hmdb
3a,6b,7b-Trihydroxy-5b-cholan-24-oic acid	hmdb
3a,6b,7b-trihydroxy-5b-Cholanate	hmdb
3a,6b,7b-trihydroxy-5b-Cholanic acid	hmdb
3a,6b,7b-Trihydroxy-5b-cholanoate	hmdb
3a,6b,7b-Trihydroxy-5b-cholanoic acid	hmdb
3alpha,6beta,7beta-Trihydroxy-5beta-cholan-24-Oate	Generator
3alpha,6beta,7beta-Trihydroxy-5beta-cholan-24-Oic acid	Kegg
3α,6β,7β-trihydroxy-5β-cholan-24-Oate	Generator
3α,6β,7β-trihydroxy-5β-cholan-24-Oic acid	Generator
5b-Cholanate-3a,6b,7b-triol	Generator
5b-Cholanic acid-3a,6b,7b-triol	hmdb
5beta-Cholanate-3alpha,6beta,7beta-triol	Generator
5beta-Cholanic acid-3alpha,6beta,7beta-triol	Kegg
5β-cholanate-3α,6β,7β-triol	Generator
5β-cholanic acid-3α,6β,7β-triol	Generator
b-Muricholate	Generator
b-Muricholic acid	hmdb
beta-Muricholate	Generator
beta-Muricholic acid	hmdb
β-muricholate	Generator
β-muricholic acid	Generator

Chemical Formula

C24H40O5

IUPAC name

(4R)-4-[(1S,2R,5R,7R,8S,9R,10S,11S,14R,15R)-5,8,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

InChI Identifier

InChI=1S/C24H40O5/c1-13(4-7-19(26)27)15-5-6-16-20-17(9-11-23(15,16)2)24(3)10-8-14(25)12-18(24)21(28)22(20)29/h13-18,20-22,25,28-29H,4-12H2,1-3H3,(H,26,27)/t13-,14-,15-,16+,17+,18+,20+,21+,22-,23-,24-/m1/s1

InChI Key

DKPMWHFRUGMUKF-CRKPLTDNSA-N

Isomeric SMILES

[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@@H](O)[C@@H](O)[C@]2([H])C[C@H](O)CC[C@]12C

Average Molecular Weight

408.5714

Monoisotopic Molecular Weight

408.28757439

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Trihydroxy bile acids, alcohols and derivatives

Alternative Parents