Chenodeoxycholic acid

Chenodeoxycholic acid

Names
IUPAC names chenodiol OR 3α,7α-dihydroxy-5β-cholanic acid OR 5β-cholanic acid-3α,7α-diol OR (R)-((3R,5S,7R,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy -10,13-dimethylhexadecahydro- 1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid
Identifiers
CAS Number	474-25-9 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:16755 N
ChEMBL	ChEMBL240597 N
ChemSpider	9728 Y
DrugBank	DB06777 N
ECHA InfoCard	100.006.803
IUPHAR/BPS	608
KEGG	C02528 N
UNII	0GEI24LG0J Y
InChI InChI=1S/C24H40O4/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/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17-,18+,19+,20-,22+,23+,24-/m1/s1 Y Key: RUDATBOHQWOJDD-BSWAIDMHSA-N Y InChI=1/C24H40O4/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/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17-,18+,19+,20-,22+,23+,24-/m1/s1 Key: RUDATBOHQWOJDD-BSWAIDMHBF
SMILES C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2[C@@H](C[C@H]4[C@@]3(CC[C@H](C4)O)C)O)C
Properties
Chemical formula	C24H40O4
Molar mass	392.57 g/mol
Melting point	165 to 167 °C (329 to 333 °F; 438 to 440 K)
Pharmacology
ATC code	A05AA01 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Chenodeoxycholic acid (also known as chenodesoxycholic acid, chenocholic acid and 3α,7α-dihydroxy-5β-cholan-24-oic acid) is a bile acid. It occurs as a white crystalline substance insoluble in water but soluble in alcohol and acetic acid, with melting point at 165-167 °C. Salts of this carboxylic acid are called chenodeoxycholates. Chenodeoxycholic acid is one of the main bile acids produced by the liver.

It was first isolated from the bile of the domestic goose, which gives it the "cheno" portion of its name (Greek: χήν = goose).

Chenodeoxycholic acid and cholic acid are the two primary bile acids in humans. Some other mammals have muricholic acid or deoxycholic acid rather than chenodeoxycholic acid.

Chenodeoxycholic acid is synthesized in the liver from cholesterol by a process which involves several enzymatic steps. Like other bile acids, it can be conjugated in the liver with taurine or glycine, forming taurochenodeoxycholate or glycochenodeoxycholate. Conjugation results in a lower pKa. This means the conjugated bile acids are ionized at the usual pH in the intestine and will stay in the gastrointestinal tract until reaching the ileum where most will be reabsorbed. Bile acids form micelles which facilitate lipid digestion. After absorption, they are taken up by the liver and resecreted, so undergoing an enterohepatic circulation. Unabsorbed chenodeoxycholic acid can be metabolised by bacteria in the colon to form the secondary bile acid known as lithocholic acid.