Structure Database (LMSD)

Common Name
Tetrahydrodeoxycortisol
Systematic Name
3α,17,21-trihydroxy-5β-pregnan-20-one
Synonyms
  • Tetrahydro-11-deoxy Cortisol
  • THS
  • tetrahydro compound S
LM ID
LMST05030014
Formula
Exact Mass
Calculate m/z
350.24571
Sum Composition
Status
Curated



Classification

Biological Context

Tetrahydro-11-deoxy cortisol (THS) is the primary urinary metabolite of 11-deoxycortisol.1,2 Urinary excretion of THS is elevated in patients with 11β-hydroxylase deficiency, a condition resulting from mutations in the cytochrome P450 (CYP) isoform CYP11B1. Urinary levels of THS are also elevated in patients with adrenocortical carcinoma (ACC) and adrenocortical adenoma (ACA) but are higher in patients with ACC compared to ACA.3,4

This information has been provided by Cayman Chemical

References

1. Keavney, B., Mayosi, B., Gaukrodger, N., et al. Genetic variation at the locus encompassing 11-β hydroxylase and aldosterone synthase accounts for heritability in cortisol precursor (11-deoxycortisol) urinary metabolite excretion. J. Clin. Endocrinol. Metab. 90(2), 1072-1077 (2005).
2. Nguyen, H.-H., Eiden-Plach, A., Hannemann, F., et al. Phenotypic, metabolic, and molecular genetic characterization of six patients with congenital adrenal hyperplasia caused by novel mutations in the CYP11B1 gene. J. Steroid Biochem. Mol. Biol. 155(Pt A), 126-134 (2016).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Homo sapiens (#9606)
Mammalia (#40674)
Isolation of pregnane-3-alpha, 17-alpha, 21-triol-20-one (tetrahydro compound S) from the urine of a woman with metastatic adrenocortical carcinoma.,
J Clin Endocrinol Metab, 1954
Pubmed ID: 13163152

String Representations

InChiKey (Click to copy)
UPTAPIKFKZGAGM-FAIYVORSSA-N
InChi (Click to copy)
InChI=1S/C21H34O4/c1-19-8-5-14(23)11-13(19)3-4-15-16(19)6-9-20(2)17(15)7-10-21(20,25)18(24)12-22/h13-17,22-23,25H,3-12H2,1-2H3/t13-,14-,15-,16+,17+,19+,20+,21+/m1/s1
SMILES (Click to copy)
[C@@]12([H])CC[C@]3([H])C[C@H](O)CC[C@]3(C)[C@@]1([H])CC[C@]1(C)[C@@](O)(C(=O)CO)CC[C@@]21[H]

Other Databases

KEGG ID
HMDB ID
CHEBI ID
PubChem CID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 25
Rings 4
Aromatic Rings 0
Rotatable Bonds 2
Van der Waals Molecular Volume 354.94
Topological Polar Surface Area 77.76
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 4
logP 3.54
Molar Refractivity 96.29

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Created at
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Updated at
9th Feb 2024