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Structure Database (LMSD)

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Common Name

Hyocholic acid

Systematic Name

3α,6α,7α-Trihydroxy-5β-cholan-24-oic Acid

Synonyms

HCA
gamma-MCA
gamma-Muricholic Acid

LM ID

LMST04010064

Formula

C₂₄H₄₀O₅

Exact Mass

Calculate m/z

408.287575

Sum Composition

ST 24:1;O5

Status

Curated

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Classification

Biological Context

Hyocholic acid is a primary bile acid in pigs and other mammals.¹ It has also been found in urine samples from patients with cholestasis.² Hyocholic acid is converted by gut microflora primarily to taurohyocholate and, to a lesser extent, taurocholic acid and tauro-β-muricholic acid in mice.³ Hyocholic acid has low toxicity against human hepatoma HepG2 cells.^3,4

This information has been provided by Cayman Chemical

References

1. van Berge Henegouwen, G.P., Brandt, K.H., Eyssen, H., et al. Sulphated and unsulphated bile acids in serum, bile, and urine of patients with cholestasis. Gut 17(11), 861-869 (1976).

2. Wang, D.Q.-H., Tazuma, S., Cohen, D.E., et al. Feeding natural hydrophilic bile acids inhibits intestinal cholesterol absorption: Studies in the gallstone-susceptible mouse. Am. J. Physiol Gastrointest. Liver Physiol. 285(3), G494-G502 (2003).

3. Perreault, M., Bialek, A., Trottier, J., et al. Role of glucuronidation for hepatic detoxification and urinary elimination of toxic bile acids during biliary obstruction. PLoS One 8(11), e80994 (2013).

4. Lundell, K., and Wikvall, K. Species-specific and age-dependent bile acid composition: Aspects on CYP8B and CYP4A subfamilies in bile acid biosynthesis. Curr. Drug Metab. 9(4), 323-331 (2008).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Identification of bile acids in the serum and urine in cholestasis. Evidence for 6alpha-hydroxylation of bile acids in man.,
Biochem J, 1976

Pubmed ID: 938463

String Representations

InChiKey (Click to copy)

DKPMWHFRUGMUKF-KWXDGCAGSA-N

InChi (Click to copy)

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

SMILES (Click to copy)

C1[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@@]([H])([C@]([H])(C)CCC(O)=O)CC[C@@]4([H])[C@]3([H])[C@H](O)[C@H](O)[C@]2([H])C[C@H](O)C1