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Structure Database (LMSD)

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Common Name

Tetrahydrocortisol

Systematic Name

3α,11β,17,21-tetrahydroxy-5β-pregnan-20-one

Synonyms

Urocortisol
5b-Tetrahydrocortisol

LM ID

LMST02030143

Formula

C₂₁H₃₄O₅

Exact Mass

Calculate m/z

366.240625

Sum Composition

ST 21:1;O5

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

5β-Tetrahydrocortisol is an endogenous metabolite of hydrocortisone (cortisol).^1,2 It is also an intermediate in the biosynthesis of β-cortol .² It is formed from cortisol by steroid 5β-reductase and is dehydrogenated by 20β-hydroxysteroid dehydrogenase (20β-HSD) to produce β-cortol in the liver.^3,1,2 Urinary levels of 5β-tetrahydrocortisol have been used as a marker for cortisol production and are associated with metabolic syndrome in obese individuals.⁴

This information has been provided by Cayman Chemical

References

1. Kosicka, K., Siemiątkowska, A., Pałka, D., et al. Detailed analysis of cortisol, cortisone and their tetrahydro- and allo-tetrahydrometabolites in human urine by LC-MS/MS. J. Pharm. Biomed. Anal. 140, 174-181 (2017).

2. Shackleton, C.H.L. Role of a disordered steroid metabolome in the elucidation of sterol and steroid biosynthesis. Lipids 47(1), 1-12 (2012).

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).

4. 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).

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String Representations

InChiKey (Click to copy)

AODPIQQILQLWGS-GXBDJPPSSA-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/h12-16,18,22-24,26H,3-11H2,1-2H3/t12-,13-,14+,15+,16+,18-,19+,20+,21+/m1/s1

SMILES (Click to copy)

C[C@@]12[C@]3([H])[C@]([H])([C@@]4([H])[C@@](C[C@@H]3O)(C)[C@](C(CO)=O)(O)CC4)CC[C@]1([H])C[C@H](O)CC2