ChemFOnt: Showing chemical card for Desoxycorticosterol (CFc000334288)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:15:16 UTC

Chemfont ID

CFc000334288

Molecule Identification

Common Name

Desoxycorticosterol

Definition

Desoxycorticosterol, also known as 21-hydroxy-4-pregnene-3,20-dione or 21-hydroxyprogesterone, is a member of the class of compounds known as 21-hydroxysteroids. 21-hydroxysteroids are steroids carrying a hydroxyl group at the 21-position of the steroid backbone. Thus, desoxycorticosterol is considered to be a steroid lipid molecule. Desoxycorticosterol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Desoxycorticosterol can be synthesized from progesterone. Desoxycorticosterol can also be synthesized into 11-deoxycorticosterone-21-hemisuccinate and 5beta-dihydrodeoxycorticosterone. Desoxycorticosterol can be found in rice, which makes desoxycorticosterol a potential biomarker for the consumption of this food product. Desoxycorticosterol can be found primarily in amniotic fluid and blood, as well as throughout all human tissues. In humans, desoxycorticosterol is involved in the steroidogenesis. Desoxycorticosterol is also involved in several metabolic disorders, some of which include corticosterone methyl oxidase I deficiency (CMO I), 21-hydroxylase deficiency (CYP21), corticosterone methyl oxidase II deficiency - CMO II, and 11-beta-hydroxylase deficiency (CYP11B1). Desoxycorticosterol is a non-carcinogenic (not listed by IARC) potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
21-Hydroxy-4-pregnene-3,20-dione	ChEBI
21-Hydroxyprogesterone	ChEBI
4-Pregnen-21-ol-3,20-dione	ChEBI
Cortexone	ChEBI
DESOXYCORTICOSTERONE	ChEBI
Desoxycortone	ChEBI
DOC	ChEBI
Kendall's desoxy compound b	ChEBI
Reichstein's substance Q	ChEBI
11-Dehydroxycorticosterone	HMDB
11-Deoxy-corticosterone	HMDB
11-Deoxycorticosterone	HMDB
11-Desoxycorticosterone	HMDB
21-Hydroxy-3,20-dioxopregn-4-ene	HMDB
21-Hydroxy-D4-pregnane-3,20-dione	HMDB
21-Hydroxy-D4-pregnene-3,20-dione	HMDB
21-Hydroxy-pregn-4-ene-3,20-dione	HMDB
21-Hydroxy-progesterone	HMDB
21-Hydroxypregn-4-ene-3,20-dione	HMDB
D4-Pregnene-21-ol-3,20-dione	HMDB
Deoxycortone	HMDB
Doca	HMDB
11-Decorticosterone	HMDB
21 Hydroxyprogesterone	HMDB
11 Decorticosterone	HMDB
21 Hydroxy 4 pregnene 3,20 dione	HMDB
Deoxycorticosterone	ChEBI

Chemical Formula

C₂₁H₃₀O₃

Average Molecular Weight

330.4611

Monoisotopic Molecular Weight

330.219494826

IUPAC Name

(1S,2R,10S,11S,14S,15S)-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

Traditional Name

(1S,2R,10S,11S,14S,15S)-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

CAS Registry Number

64-85-7

SMILES

[H][C@@]12CC[C@H](C(=O)CO)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C

InChI Identifier

InChI=1S/C21H30O3/c1-20-9-7-14(23)11-13(20)3-4-15-16-5-6-18(19(24)12-22)21(16,2)10-8-17(15)20/h11,15-18,22H,3-10,12H2,1-2H3/t15-,16-,17-,18+,20-,21-/m0/s1

InChI Key

ZESRJSPZRDMNHY-YFWFAHHUSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Hydroxysteroids

Direct Parent

21-hydroxysteroids

Alternative Parents

Substituents

Progestogin-skeleton
21-hydroxysteroid
Pregnane-skeleton
20-oxosteroid
3-oxo-delta-4-steroid
3-oxosteroid
Oxosteroid
Delta-4-steroid
Cyclohexenone
Alpha-hydroxy ketone
Cyclic ketone
Ketone
Organic oxygen compound
Organooxygen compound
Primary alcohol
Carbonyl group
Hydrocarbon derivative
Alcohol
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3-oxo Delta(4)-steroid (CHEBI:16973 )
20-oxo steroid (CHEBI:16973 )
mineralocorticoid (CHEBI:16973 )
21-hydroxy steroid (CHEBI:16973 )
Pregnane and derivatives [Fig] (C03205 )
C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives (C03205 )
Mineralocorticoids (C03205 )
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030087 )

Functional Ontology

Physiological effect

Health effect

Endocrine system disorder

Congenital Adrenal Hyperplasia (HMDB: HMDB0000016)

Disposition

Biological location

Cellular substructure

Organelle

Mitochondrion (HMDB: HMDB0000016)
Endoplasmic reticulum (HMDB: HMDB0000016)

Tissue

All Tissues (HMDB: HMDB0000016)

Nervous tissue

Hepatic tissue (HMDB: HMDB0000016)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0000016)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0000016)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000016)

Source

Endogenous

Endogenous (HMDB: HMDB0000016)

Animal

Animal (HMDB: HMDB0000016)

Exogenous

Food

Food (HMDB: HMDB0000016)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Role

Biological role

Membrane stabilizer (HMDB: HMDB0000016)

Molecular messenger

Hormone (HMDB: HMDB0000016)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0000016)

Indirect biological role

Metabotoxin

Metabotoxin (HMDB: HMDB0000016)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.017 g/L	ALOGPS
logP	3.1	ALOGPS
logP	3.33	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	13.86	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	94.41 m³·mol⁻¹	ChemAxon
Polarizability	38.19 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon