LIPID MAPS

Structure Database (LMSD)

Download as... MDLMOL SDF CSV TSV PNG SVG

Systematic Name

5β-Cholestane-3α,7α,12α,25-tetrol

Synonyms

LM ID

LMST04030037

Formula

C₂₇H₄₈O₄

Exact Mass

Calculate m/z

436.355261

Sum Composition

ST 27:0;O4

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View NP-MRD ID(NMR) spectrum

Classification

Biological Context

5β-Cholestane-3α,7α,12α,25-tetrol is a bile acid alcohol.^1,2,3 It induces activation of G protein-coupled bile acid receptor 1 (GPBAR1), also known as TGR5, in HEK293 cells expressing the human receptor when used at concentrations ranging from 0.1 to 10 µM.¹ Blood, fecal, and bile levels of 5β-cholestane-3α,7α,12α,25-tetrol are increased in patients with cerebrotendinous xanthomatosis (CTX), a progressive metabolic leukodystrophy.^1,2,3

This information has been provided by Cayman Chemical

References

1. Iguchi, Y., Yamaguchi, M., Sato, H., et al. Bile alcohols function as the ligands of membrane-type bile acid-activated G protein-coupled receptor. J. Lipid Res. 51(6), 1432-1441 (2010).

2. DeBarber, A.E., Kalfon, L., Fedida, A., et al. Newborn screening for cerebrotendinous xanthomatosis is the solution for early identification and treatment. J. Lipid Res. 59(11), 2214-2222 (2018).

3. Dayal, B., Shefer, S., Tint, G.S., et al. Synthesis of 5β-cholestane-3α, 7α, 12α, 25-tetrol and 5β-cholestane-3α, 7α, 24ξ, 25-pentol. J. Lipid Res. 17(1), 74-77 (1976).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Bile alcohol profiles in bile, urine, and feces of a patient with cerebrotendinous xanthomatosis.,
J Biochem, 1986

Pubmed ID: 3700361

Alligator mississippiensis (#8496)

Biliary bile acids, bile alcohols, and sterols of Alligator mississippiensis.,
J Lipid Res, 1980

Pubmed ID: 7354247

String Representations

InChiKey (Click to copy)

NTIXPPFPXLYJCT-RNUSRIHUSA-N

InChi (Click to copy)

InChI=1S/C27H48O4/c1-16(7-6-11-25(2,3)31)19-8-9-20-24-21(15-23(30)27(19,20)5)26(4)12-10-18(28)13-17(26)14-22(24)29/h16-24,28-31H,6-15H2,1-5H3/t16-,17+,18-,19-,20+,21+,22-,23+,24+,26+,27-/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)CCCC(O)(C)C)CC[C@@]4([H])[C@]3([H])[C@H](O)C[C@]2([H])C[C@H](O)C1