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Structure Database (LMSD)

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Common Name

Dehydrocholic acid

Systematic Name

3,7,12-Trioxo-5β-cholan-24-oic Acid

Synonyms

DehydroCA

LM ID

LMST04010106

Formula

C₂₄H₃₄O₅

Exact Mass

Calculate m/z

402.240626

Sum Composition

ST 24:4;O5

Status

Curated

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Classification

Biological Context

Dehydrocholic acid is a synthetic bile acid and a derivative of cholic acid .¹ It increases bile flow by 2.7-fold and decreases biliary levels of phospholipids, cholesterol, and bilirubin in conscious dogs when administered at a dose of 50 mg/kg.² Dehydrocholic acid (1 µmol/min/0.1 kg) increases bile flow by 253% and decreases the secretion rate of phospholipids and cholesterol by 64 and 94%, respectively, in rats when infused intravenously at a dose of 2 µmol/min/0.1 kg.³

This information has been provided by Cayman Chemical

References

1. Soloway, R.D., Hofmann, A.F., Thomas, P.J., et al. Triketocholanoic (dehydrocholic) acid. Hepatic metabolism and effect on bile flow and biliary lipid secretion in man. J. Clin. Invest. 52(3), 715-724 (1973).

2. Yanaura, S., and Ishikawa, S. Choleretic properties of ursodeoxycholic acid and chenodeoxycholic acid in dogs. Jpn. J. Pharmacol. 28(3), 383-389 (1978).

3. Yousef, I.M., Mignault, D., Weber, A.M., et al. Influence of dehydrocholic acid on the secretion of bile acids and biliary lipids in rats. Digestion 45(1), 40-51 (1990).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

synthetic construct (#32630)

Triketocholanoic (dehydrocholic) acid. Hepatic metabolism and effect on bile flow and biliary lipid secretion in man.,
J Clin Invest, 1973

Pubmed ID: 4685091

String Representations

InChiKey (Click to copy)

OHXPGWPVLFPUSM-KLRNGDHRSA-N

InChi (Click to copy)

InChI=1S/C24H34O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-14,16-18,22H,4-12H2,1-3H3,(H,28,29)/t13-,14+,16-,17+,18+,22+,23+,24-/m1/s1

SMILES (Click to copy)

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