LIPID MAPS

Structure Database (LMSD)

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Common Name

alpha-Cortolone

Systematic Name

5β-11-oxo-pregnane-3α,11β,17,20S,21-tetrol

Synonyms

Cortolone

LM ID

LMST02030227

Formula

C₂₁H₃₄O₅

Exact Mass

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366.240626

Sum Composition

ST 21:1;O5

Status

Curated

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Classification

Biological Context

α-Cortolone is a metabolite of the glucocorticoid cortisol (hydrocortisone).¹ It is formed from cortisol by 20α-hydroxysteroid dehydrogenase (20α-HSD) via a tetrahydrocortisone (THE) intermediate. Urinary levels of α-cortolone are decreased in patients with severe anorexia nervosa and in postmenopausal women with endometrial adenocarcinoma compared to postmenopausal women without endometrial adenocarcinoma.^2,3

This information has been provided by Cayman Chemical

References

1. Espiard, S., McQueen, J., Sherlock, M., et al. Improved urinary cortisol metabolome in Addison disease: A prospective trial of dual-release hydrocortisone. J. Clin. Endocrinol. Metab. 106(3), 814-825 (2021).

2. Wassif, W.S., McLoughlin, D.M., Vincent, R.P., et al. Steroid metabolism and excretion in severe anorexia nervosa: Effects of refeeding. Am. J. Clin. Nutr. 93(5), 911-917 (2011).

3. Bufa, A., Bíró, I., Poór, V., et al. Altered urinary profiles of endogenous steroids in postmenopausal women with adenocarcinoma endometrii. Gynecol. Endocrinol. 26(1), 10-15 (2010).

Reactions

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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

DOI: 10.1016/S0021-9258(18)64606-X

Homo sapiens (#9606)

Mammalia (#40674)

The characterization of four new metabolites of adrenocortical hormones.,
J Biol Chem, 1955

Pubmed ID: 13233247

DOI: 10.1016/s0021-9258(18)71132-0

String Representations

InChiKey (Click to copy)

JXCOSKURGJMQSG-AZQJGLEESA-N

InChi (Click to copy)

InChI=1S/C21H34O5/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/h12-15,17-18,22-23,25-26H,3-11H2,1-2H3/t12-,13-,14+,15+,17+,18-,19+,20+,21+/m1/s1

SMILES (Click to copy)

O[C@H]([C@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@@H](CC[C@@]4([C@@]3([H])C(C[C@]12C)=O)C)O)O)CO