Tetrahydrocorticosterone

Tetrahydrocorticosterone
Names

IUPAC name 3α,11β,21-Trihydroxy-5β-pregnan-20-one
Other names 3α,5α-Tetrahydrocorticosterone; 5β-Pregnane-3α,11β,21-triol-20-one
Identifiers
CAS Number	68-42-8^Y
3D model (Jmol)	Interactive image
ChemSpider	17215927
ECHA InfoCard	100.000.627
PubChem	65553
InChI InChI=1S/C21H34O4/c1-20-8-7-13(23)9-12(20)3-4-14-15-5-6-16(18(25)11-22)21(15,2)10-17(24)19(14)20/h12-17,19,22-24H,3-11H2,1-2H3/t12?,13?,14?,15-,16+,17?,19+,20-,21-/m0/s1 Key: RHQQHZQUAMFINJ-WAWWIEPNSA-N InChI=1/C21H34O4/c1-20-8-7-13(23)9-12(20)3-4-14-15-5-6-16(18(25)11-22)21(15,2)10-17(24)19(14)20/h12-17,19,22-24H,3-11H2,1-2H3/t12?,13?,14?,15-,16+,17?,19+,20-,21-/m0/s1 Key: RHQQHZQUAMFINJ-WAWWIEPNBT
SMILES OCC(=O)[C@H]4CC[C@H]3C2CCC1CC(O)CC[C@]1(C)[C@H]2C(O)C[C@@]34C
Properties
Chemical formula	C₂₁H₃₄O₄
Molar mass	350.50 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

3α,5α-Tetrahydrocorticosterone (3α,5α-THB), or simply tetrahydrocorticosterone (THB or THCC), is an endogenous glucocorticoid hormone.^[1]

References

↑ McInnes KJ, Kenyon CJ, Chapman KE, et al. (May 2004). "5alpha-reduced glucocorticoids, novel endogenous activators of the glucocorticoid receptor". The Journal of Biological Chemistry. 279 (22): 22908–12. doi:10.1074/jbc.M402822200. PMID 15044432.

Mineralocorticoids and antimineralocorticoids (H02)

Mineralocorticoids	11-Deoxycorticosterone (desoxycortone) 11-Deoxycortisol (cortodoxone) Aldosterone Corticosterone Cortisol (hydrocortisone) Desoxycortone acetate Desoxycortone enanthate Fludrocortisone Fludrocortisone acetate

Antimineralocorticoids	Amlodipine Benidipine Canrenoate potassium (potassium canrenoate) Canrenoic acid Canrenone Drospirenone Eplerenone Felodipine Finerenone Gestodene Nifedipine Nimodipine Nitrendipine Progesterone Spironolactone

Synthesis modifiers	Acetoxolone Aminoglutethimide Carbenoxolone Enoxolone Ketoconazole Metyrapone Mitotane Trilostane

^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III

Endogenous steroids

Precursors

Corticosteroids

Glucocorticoids	Corticosterone Cortisol Cortisone DHC Deoxycortisol Deoxycorticosterone 17α-Hydroxypregnenolone 17α-Hydroxyprogesterone Pregnenolone Progesterone THB

Mineralocorticoids	Aldosterone Corticosterone Cortisol Deoxycortisol Deoxycorticosterone 5α-Dihydroaldosterone 16α,18-Dihydroxy-11-deoxycorticosterone 18-Hydroxy-11-deoxycorticosterone 18-Hydroxycorticosterone 18-Hydroxydeoxycorticosterone

Sex steroids

Androgens	11-Ketotestosterone 7β-Hydroxyepiandrosterone 11β-Hydroxyandrostenedione 4-Androstenedione 5-Androstenediol Adrenosterone (11-ketoandrostenedione) Androsterone DHEA DHEA sulfate Dihydrotestosterone Epiandrosterone Epitestosterone 16α-Hydroxyandrostenedione 16α-Hydroxy-DHEA 16α-Hydroxy-DHEA sulfate Testosterone Metabolites: 3α-Androstanediol 3α-Androstanediol glucuronide 3β-Androstanediol 3α,5β-Androstanediol 3β,5β-Androstanediol 5β-Androstanedione 5β-Dihydrotestosterone Androstanetriols Androsterone glucuronide Dihydrotestosterone glucuronide Dihydrotestosterone sulfate Etiocholanolone Etiocholanolone glucuronide Epietiocholanolone Testosterone glucuronide Testosterone sulfate

Estrogens	27-Hydroxycholesterol 3α-Androstanediol 3β-Androstanediol 4-Androstenedione 5-Androstenediol DHEA DHEA sulfate 7-Keto-DHEA 7α-Hydroxy-DHEA 16α-Hydroxy-DHEA Estetrol Estradiol Estrone Estriol 16β-Epiestriol (16β-hydroxyestradiol) 17α-Epiestriol (16α-hydroxy-17α-estradiol) 16β,17α-Epiestriol (16β-hydroxy-17α-estradiol) 2-Hydroxyestradiol 2-Hydroxyestrone 2-Methoxyestradiol 4-Hydroxyestradiol 4-Hydroxyestrone 16α-Hydroxyestrone Metabolites: Estradiol glucuronide Estradiol sulfate Estrone glucuronide Estrone sulfate Estriol glucuronide Estriol sulfate Lipoidal estradiol (e.g., estradiol stearate, estradiol palmitate)

Progestogens	Progesterone 16α-Hydroxyprogesterone 17α-Hydroxyprogesterone 20α-Dihydroprogesterone 5α-Dihydroprogesterone Deoxycorticosterone 5α-DHDOC Metabolites: Pregnanediol Pregnanediol glucuronide Pregnanetriol

Neurosteroids

Cholestane: 24S-Hydroxycholesterol
Cholesterol

Androstane: 3α-Androstanediol
3α-Androstenol
7-Keto-DHEA
7α-Hydroxy-DHEA
7β-Hydroxy-DHEA
7α-Hydroxyepiandrosterone
7β-Hydroxyepiandrosterone
Androsterone
DHEA
DHEA sulfate
Etiocholanolone

Others

Others: 11α-Hydroxyprogesterone
11β-Hydroxyprogesterone

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Tetrahydrocorticosterone

See also

References