FComEx: Nutriacholic acid (PC000496)

Record Information

Version

1.0

Creation date

2015-10-09 22:30:57 UTC

Update date

2017-01-19 02:36:26 UTC

FoodComEx ID

PC000496

FoodDB Record

FDB022059

Chemical Information

Name

Nutriacholic 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. (PMID: 11316487, 16037564, 12576301, 11907135) [HMDB]

CAS Number

4651-67-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
3a-hydroxy-7-oxo-5b-cholanoate	hmdb
3a-hydroxy-7-oxo-5b-cholanoic acid	hmdb
5b-Cholanic acid-3a-ol-7-one	hmdb
7-Ketochenodeoxycholate	hmdb
7-Ketochenodeoxycholic acid	hmdb
7-Ketolithocholate	hmdb
7-Ketolithocholic acid	hmdb
7-Oxo-3a-hydroxycholan-24-oate	hmdb
7-Oxo-3a-hydroxycholan-24-oic acid	hmdb
7-Oxolithocholate	hmdb
7-Oxolithocholic acid	hmdb
Nutriacholate	hmdb
Nutriacholic acid	hmdb

Chemical Formula

C24H38O4

IUPAC name

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

InChI Identifier

InChI=1S/C24H38O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-19,22,25H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16+,17?,18-,19-,22-,23-,24+/m0/s1

InChI Key

DXOCDBGWDZAYRQ-QPVZPPSOSA-N

Isomeric SMILES

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

Average Molecular Weight

390.5561

Monoisotopic Molecular Weight

390.277009704

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Monohydroxy bile acids, alcohols and derivatives

Alternative Parents