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Structure Database (LMSD)

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Systematic Name

3β-Hydroxy-chol-5-en-24-oic Acid

Synonyms

LM ID

LMST04010201

Formula

C₂₄H₃₈O₃

Exact Mass

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374.282095

Sum Composition

ST 24:2;O3

Status

Curated

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Classification

Biological Context

Cholenic acid is a monohydroxy bile acid.¹ It is a cholesterol oxidation product formed by 7α-hydroxylation of 27-hydroxycholesterol , as well as a precursor in the biosynthesis of chenodeoxycholic acid . Levels of cholenic acid are increased in patients with neonatal liver disease harboring mutations in CYP7A1, the gene encoding 7α-hydroxylase, as well as in patients with intrahepatic and extrahepatic cholestasis.^2,3

This information has been provided by Cayman Chemical

References

1. Lee, C., Martin, K.O., and Javitt, N.B. Bile acid synthesis: 7α-Hydroxylation of intermediates in the sterol 27-hydroxylase metabolic pathway. J. Lipid. Res. 37(6), 1356-1362 (2006).

2. Setchell, K.D.R., Schwarz, M., O'Connell, N.C., et al. Identification of a new inborn error in bile acid synthesis: Mutation of the oxysterol 7α-hydroxylase gene causes severe neonatal liver disease. J. Clin. Invest. 102(9), 1690-1703 (1998).

3. Sugiyama, K., Okuyama, S., Imoto, M., et al. Clinical evaluation of serum 3β-hydroxy-5-cholenoic acid in hepatobiliary disease. Gastroenterologia Japonica 21(6), 608-616 (1986).

String Representations

InChiKey (Click to copy)

HIAJCGFYHIANNA-QIZZZRFXSA-N

InChi (Click to copy)

InChI=1S/C24H38O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h5,15,17-21,25H,4,6-14H2,1-3H3,(H,26,27)/t15-,17+,18+,19-,20+,21+,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])CC=C2C[C@@H](O)C1