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Structure Database (LMSD)

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Common Name

Norcholic acid

Systematic Name

24-nor-3α,7α,12α-trihydroxy-5β-cholan-23-oic acid

Synonyms

LM ID

LMST04060019

Formula

C₂₃H₃₈O₅

Exact Mass

Calculate m/z

394.271925

Sum Composition

ST 23:1;O5

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

Norcholic acid is a bile acid and 23-carbon derivative of cholic acid .¹ Levels of norcholic acid are increased in the urine of patients with liver cirrhosis or cerebrotendinous xanthomatosis (CTX), an inborn error of metabolism characterized by a deficiency in the mitochondrial enzyme sterol 27-hydrolylase (CYP27A1) that leads to progressive neurological symptoms.^2,3,4

This information has been provided by Cayman Chemical

References

1. Pilo de la Fuente, B., Sobrido, M.J., Girós, M., et al. Usefulness of cholestanol levels in the diagnosis and follow-up of patients with cerebrotendinous xanthomatosis. Neurologia 26(7), 397-404 (2011).

2. Nakatomi, F., Kihira, K., Kuramoto, T., et al. Intestinal absorption and metabolism of norcholic acid in rats. J. Pharmacobiodyn 8(7), 557-563 (1985).

3. Bremmelgaard, A., and Sjövall, J. Bile acid profiles in urine of patients with liver diseases. Eur. J. Clin. Invest. 9(5), 341-348 (1979).

4. Kuramoto, T., Furukawa, Y., Nishina, T., et al. Identification of short side chain bile acids in urine of patients with cerebrotendinous xanthomatosis. J. Lipid Res. 10, 1895-1902 (1990).

String Representations

InChiKey (Click to copy)

SHUYNJFEXPRUGR-RTCCEZQESA-N

InChi (Click to copy)

InChI=1S/C23H38O5/c1-12(8-20(27)28)15-4-5-16-21-17(11-19(26)23(15,16)3)22(2)7-6-14(24)9-13(22)10-18(21)25/h12-19,21,24-26H,4-11H2,1-3H3,(H,27,28)/t12-,13+,14-,15-,16+,17+,18-,19+,21+,22+,23-/m1/s1

SMILES (Click to copy)

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