Showing Metabocard for 5beta-dihydrocortisol (BASm0000034)

Common Name

5beta-dihydrocortisol

Description

Dihydrocortisol is the product of the enzyme steroid 5-beta-reductase (EC 1.3.1.3), which catalyzes the reduction of progesterone, androstenedione, 17-alpha-hydroxyprogesterone, testosterone, aldosterone, corticosterone, and cortisol to 5-beta-reduced metabolites. A deficiency in this enzyme is associated with a congenital defect in bile acid synthesis (OMIM: 235555 ). Dihydrocortisol is the substrate of the enzyme 3-alpha-hydroxysteroid dehydrogenase (EC 1.1.1.225, 1.1.1.213, 1.3.1.20, 1.1.1.50), and is an intermediate in bile acid biosynthesis, C21-steroid hormone metabolism, androgen and estrogen metabolism, and the metabolism of xenobiotics by cytochrome P450 (KEGG).

Structure

Molecular Formula

C₂₁H₃₂O₅

Average Mass

364.47580

Monoisotopic Mass

364.22497

IUPAC Name

(1S,2S,7R,10S,11S,14R,15S,17S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-one

Traditional Name

Dihydrocortisol

CAS Registry Number

1482-50-4

SMILES

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

InChI Identifier

InChI=1S/C21H32O5/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/h12,14-16,18,22,24,26H,3-11H2,1-2H3/t12-,14+,15+,16+,18-,19+,20+,21+/m1/s1

InChI Key

ACSFOIGNUQUIGE-AIPUTVCKSA-N

CHEBI ID

CHEBI:732

HMDB ID

HMDB0003259

Pathways

Name	SMPDB/PathBank
Steroidogenesis
Congenital Lipoid Adrenal Hyperplasia (CLAH) or Lipoid CAH
Adrenal Hyperplasia Type 5 or Congenital Adrenal Hyperplasia due to 17 Alpha-hydroxylase Deficiency
Adrenal Hyperplasia Type 3 or Congenital Adrenal Hyperplasia due to 21-hydroxylase Deficiency
17-alpha-hydroxylase deficiency (CYP17)
11-beta-hydroxylase deficiency (CYP11B1)
21-hydroxylase deficiency (CYP21)
Corticosterone methyl oxidase I deficiency (CMO I)
Corticosterone methyl oxidase II deficiency - CMO II
Apparent mineralocorticoid excess syndrome
3-Beta-Hydroxysteroid Dehydrogenase Deficiency

State

Not Available

Water Solubility

2.16e-01 g/l

logP

1.80

logS

-3.23

pKa (Strongest Acidic)

12.58

pKa (Strongest Basic)

-2.84

Hydrogen Acceptor Count

Hydrogen Donor Count

Polar Surface Area

94.83 Å²

Rotatable Bond Count

Physiological Charge

Formal Charge

Refractivity

96.57 m³·mol⁻¹

Polarizability

40.10

We require the use of cookies for essential features like storing your previously submitted BASys2 queries. Rejecting the usage of cookies will result in certain features being disabled. By clicking ACCEPT or continuing to use the website you are agreeing to our use of cookies.