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Structure Database (LMSD)

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Common Name

Trihydroxycholestanoic Acid

Systematic Name

3α,7α,12α-trihydroxy-5β-cholestan-26-oic acid

Synonyms

3alpha,7alpha,12alpha-trihydroxy-5beta-cholestanoic acid
3alpha,7alpha,12alpha-trihydroxy-5beta-cholestanoate
(THCA

LM ID

LMST04030001

Formula

C₂₇H₄₆O₅

Exact Mass

Calculate m/z

450.334526

Sum Composition

ST 27:1;O5

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

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Classification

Biological Context

Trihydroxycholestanoic acid is an intermediate in the biosynthesis of cholic acid .¹ Elevated plasma levels of trihydroxycholestanoic acid have been found in patients with Zellweger syndrome, a neurological disorder characterized by mutations in PEX genes which result in defects in peroxisome formation.^2,3

This information has been provided by Cayman Chemical

References

1. Klouwer, F.C.C., Berendse, K., Ferdinandusse, S., et al. Zellweger spectrum disorders: Clinical overview and management approach. Orphanet J. Rare Dis. 10, 151 (2015).

2. Ferdinandusse, S., Overmars, H., Denis, S., et al. Plasma analysis of di- and trihydroxycholestanoic acid diastereoisomers in peroxisomal α-methylacyl-CoA racemase deficiency. J. Lipid Res. 42(1), 137-141 (2001).

3. Keane, M.H., Overmars, H., Wikander, T.M., et al. Bile acid treatment alters hepatic disease and bile acid transport in peroxisome-deficient PEX2 Zellweger mice. Hepatology 45(4), 982-997 (2007).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Plasma analysis of di- and trihydroxycholestanoic acid diastereoisomers in peroxisomal alpha-methylacyl-CoA racemase deficiency.,
J Lipid Res, 2001

Pubmed ID: 11160375

String Representations

InChiKey (Click to copy)

CNWPIIOQKZNXBB-VCVMUKOKSA-N

InChi (Click to copy)

InChI=1S/C27H46O5/c1-15(6-5-7-16(2)25(31)32)19-8-9-20-24-21(14-23(30)27(19,20)4)26(3)11-10-18(28)12-17(26)13-22(24)29/h15-24,28-30H,5-14H2,1-4H3,(H,31,32)/t15-,16?,17+,18-,19-,20+,21+,22-,23+,24+,26+,27-/m1/s1

SMILES (Click to copy)

[C@]12([C@H](O)C[C@]3([H])C[C@H](O)CC[C@]3(C)[C@@]1([H])C[C@H](O)[C@]1(C)[C@@]([H])([C@@](C)([H])CCCC(C)C(=O)O)CC[C@@]21[H])[H]