Glycodeoxycholic acid

Catalog Number	ACM360656-3
CAS	360-65-6
Structure
Synonyms	Deoxycholylglycine
IUPAC Name	2-[[(4R)-4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-Dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]acetic acid
Molecular Weight	449.63
Molecular Formula	C26H43NO5
Canonical SMILES	CC(CCC(=O)NCC(=O)O)C1CCC2C1(C(CC3C2CCC4C3(CCC(C4)O)C)O)C
InChI	InChI=1S/C26H43NO5/c1-15(4-9-23(30)27-14-24(31)32)19-7-8-20-18-6-5-16-12-17(28)10-11-25(16,2)21(18)13-22(29)26(19,20)3/h15-22,28-29H,4-14H2,1-3H3,(H,27,30)(H,31,32)/t15-,16-,17-,18+,19-,20+,21+,22+,25+,26-/m1/s1
InChI Key	WVULKSPCQVQLCU-BUXLTGKBSA-N
Boiling Point	655.6±50.0 °C
Melting Point	184 °C
Flash Point	350.3 °C
Purity	95%
Density	1.162±0.06 g/cm³
Appearance	White to off-white solid
Storage	2-8 °C
Complexity	727
Covalently-Bonded Unit Count	1
Defined Atom Stereocenter Count	10
Exact Mass	449.31412347
Heavy Atom Count	32
Hydrogen Bond Acceptor Count	5
Hydrogen Bond Donor Count	4
Isomeric SMILES	C[C@H](CCC(=O)NCC(=O)O)[C@H]1CC[C@@H]2[C@@]1([C@H](C[C@H]3[C@H]2CC[C@H]4[C@@]3(CC[C@H](C4)O)C)O)C
Monoisotopic Mass	449.31412347
Physical State	Freezer
Rotatable Bond Count	6
Topological Polar Surface Area	107 Ų

Knowledge & Learning Case Study Q&A

Role of Glycodeoxycholic Acid in Buffalo Follicular Atresia

Wei Y, et al. The Journal of Steroid Biochemistry and Molecular Biology, 2022, 221, 106115.

Buffalo follicular atresia, a process where ovarian follicles degenerate and fail to develop, has significant implications for animal reproduction and agricultural productivity. Recent research reveals a critical role for glycodeoxycholic acid (GDCA), a conjugated bile acid, in this process.
Bile acids, though abundant in mammalian follicular fluid, are not synthesized in the follicles themselves. Instead, they are transported from the bloodstream into the follicular environment, as evidenced by the expression of bile acid transporters in ovarian tissues and the absence of rate-limiting enzymes required for bile acid synthesis. The study compared healthy follicles (HF) and atretic follicles (AF), finding thirteen differential bile acid subspecies between them. Notably, free bile acids were significantly down-regulated, while conjugated forms, such as GDCA, were up-regulated in AF.
The study's targeted analysis identified GDCA as a key mediator in promoting follicular granulosa cell apoptosis and reducing steroid hormone production. This dual action contributes to follicular atresia, suggesting that the accumulation of GDCA in AF is a significant factor in accelerating this degenerative process. The upregulation of conjugated bile acids, particularly GDCA, in atretic conditions implies a potential feedback mechanism where increased GDCA levels exacerbate atresia by fostering cellular apoptosis and hormonal disruption.

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