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
3D model of Tetrahydrodeoxycortisol
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
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
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
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
Admin
Created at
-
Updated at
9th Feb 2024