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Structure Database (LMSD)

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Common Name

12-Ketochenodeoxycholic acid

Systematic Name

3α,7α-Dihydroxy-12-oxo-5β-cholan-24-oic Acid

Synonyms

3,7-Dihydroxy-12-oxocholanoic acid
12-KetoCDCA

LM ID

LMST04010176

Formula

C₂₄H₃₈O₅

Exact Mass

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406.271926

Sum Composition

ST 24:2;O5

Status

Curated

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Classification

Biological Context

12-keto Chenodeoxycholic acid (12-keto CDCA) is an intermediate in the semisynthetic synthesis of ursodeoxycholic acid and chenodeoxycholic acid from the primary bile acid cholic acid .^1,2 12-keto CDCA has been found in the gastric tissues of C57BL/6J mice, KM mice, Sprague-Dawley rats, New Zealand white rabbits, and JX black pigs.³ Fecal levels of 12-keto CDCA are increased in children with hepatic glycogen storage disease.⁴ The sodium salt of 12-keto CDCA, known as 12-monoketocholic acid (12-MKA), increases brain uptake of quinine , the analgesic effect of morphine in the hot plate test, and pentobarbital-induced sleeping time in rats when administered at a dose of 2 mg/kg.⁵ It also promotes nasal absorption of insulin and increases the duration of local anesthesia induced by lidocaine in rats.^5,6

This information has been provided by Cayman Chemical

References

1. Poša, M., Kevrešan, S., Mikov, M., et al. Effect of cholic acid and its keto derivatives on the analgesic action of lidocaine and associated biochemical parameters in rats. Eur. J. Drug Metab. Pharmacokinet. 32(2), 109-117 (2007).

2. Sutherland, J.D., Macdonald, I.A., and Forrest, T.P. The enzymic and chemical synthesis of ursodeoxycholic and chenodeoxycholic acid from cholic acid. Prep. Biochem. 12(4), 307-321 (1982).

3. Hofmann, A.F. The preparation of chenodeoxycholic acid and Its glycine and taurine conjugates. Acta Chemica Scand. 17, 173-186 (1963).

4. Zhao, A., Wang, S., Chen, W., et al. Increased levels of conjugated bile acids are associated with human bile reflux gastritis. Sci. Rep. 10(1), 11601 (2020).

5. Wang, Y., Liu, H., Dong, F., et al. Altered gut microbiota and microbial metabolism in children with hepatic glycogen storage disease: a case-control study. Transl. Pediatr. 12(4), 572-586 (2023).

6. Mikov, M., Kevresan, S., Kuhajda, K., et al. 3α,7α-dihydroxy-12-oxo-5β-cholanate as blood-brain barrier permeator. Pol. J. Pharmacol. 56(3), 367-371 (2004).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Urinary and fecal keto bile acids in liver cirrhosis.,
Clin Chim Acta, 1981

Pubmed ID: 7285341

String Representations

InChiKey (Click to copy)

MIHNUBCEFJLAGN-DMMBONCOSA-N

InChi (Click to copy)

InChI=1S/C24H38O5/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/h13-19,22,25-26H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,19-,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@H](O)C[C@]2([H])C[C@H](O)C1