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Structure Database (LMSD)

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Common Name

beta-Cortol

Systematic Name

5β-Pregnane-3α,11β,17,20R,21-pentol

Synonyms

LM ID

LMST02030229

Formula

C₂₁H₃₆O₅

Exact Mass

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368.256275

Sum Composition

ST 21:0;O5

Status

Curated

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Classification

Biological Context

β-Cortol is an endogenous metabolite of cortisol (hydrocortisone).^1,2 It is formed from cortisol via the intermediate metabolite 5β-tetrahydrocortisol, which is dehydrogenated by 20β-hydroxysteroid dehydrogenase (20β-HSD) in the liver to produce β-cortol.² Urinary levels of β-cortol have been used as a marker for cortisol production and are associated with metabolic syndrome in obese individuals.³

This information has been provided by Cayman Chemical

References

1. Krone, N., Hughes, B.A., Lavery, G.G., et al. Gas chromatography/mass spectrometry (GC/MS) remains a pre-eminent discovery tool in clinical steroid investigations even in the era of fast liquid chromatography tandem mass spectrometry (LC/MS/MS). J. Steroid Biochem. Mol. Biol. 121(3-5), 496-504 (2010).

2. Schiffer, L., Barnard, L., Baranowski, E.S., et al. Human steroid biosynthesis, metabolism and excretion are differentially reflected by serum and urine steroid metabolomes: A comprehensive review. J. Steroid Biochem. Mol. Biol. 194, 105439 (2019).

3. Baudrand, R., Campino, C., Carvajal, C.A., et al. Increased urinary glucocorticoid metabolites are associated with metabolic syndrome, hypoadiponectinemia, insulin resistance and β cell dysfunction. Steroids 76(14), 1575-1581 (2011).

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References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Metabolic transformation of hydrocortisone-4-C14 in normal men.,
J Biol Chem, 1960

Pubmed ID: 13825604

String Representations

InChiKey (Click to copy)

FFPUNPBUZDTHJI-ZFOKFBPFSA-N

InChi (Click to copy)

InChI=1S/C21H36O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h12-18,22-26H,3-11H2,1-2H3/t12-,13-,14+,15+,16+,17-,18-,19+,20+,21+/m1/s1

SMILES (Click to copy)

C1C[C@]2(C)[C@@]3([H])[C@@H](O)C[C@]4(C)[C@@](O)([C@H](O)CO)CC[C@@]4([H])[C@]3([H])CC[C@]2([H])C[C@@H]1O