ChemFOnt: Showing chemical card for 4-Androstenediol (CFc000002592)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:47:30 UTC

Chemfont ID

CFc000002592

Molecule Identification

Common Name

4-Androstenediol

Definition

4-Androstenediol is a metabolite of testosterone. Conversely, the conversion of 4-androstenediol to testosterone has been demonstrated to occur in homogenates of hyperplastic human female adrenal glands. 4-Androstenediol is an anabolic agent that has been found in increased concentration in athletes suspected of doping. 4-Androstenediol has also been found in aqueous and solid nutritional supplements that are commercially available. Studies showing that non-hormonal supplements such as vitamins, minerals, and amino acids can contain anabolic androgenic steroids not declared on the labels of the products have been published. These undeclared substances (often prohormones of testosterone) can cause health risks to consumers and might lead to positive results in sports doping control. It has been demonstrated that 4-androstenediol taken by mouth is capable of producing in vivo increases in testosterone concentration in apparently healthy young men an women (PMID: 15808000 , 15103700 , 10638382 , 15370836 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Androst-4-ene-3beta,17beta-diol	Kegg
Androst-4-ene-3b,17b-diol	Generator
Androst-4-ene-3β,17β-diol	Generator
(3b,17b)-Androst-4-ene-3,17-diol	HMDB
3b,17b-Dihydroxy-4-androstene	HMDB
4-Androstene-3b,17b-diol	HMDB
Androst-4-en-3b,17b-diol	HMDB
D4-Androstene-3b,17b-diol	HMDB
(3beta,17beta)-Androst-4-ene-3,17-diol	HMDB
(3β,17β)-Androst-4-ene-3,17-diol	HMDB
3beta,17beta-Dihydroxy-4-androstene	HMDB
3β,17β-Dihydroxy-4-androstene	HMDB
4-Androstenediol	HMDB

Chemical Formula

C₁₉H₃₀O₂

Average Molecular Weight

290.4403

Monoisotopic Molecular Weight

290.224580204

IUPAC Name

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

Traditional Name

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

CAS Registry Number

1156-92-9

SMILES

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

InChI Identifier

InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,13-17,20-21H,3-10H2,1-2H3/t13-,14-,15-,16-,17-,18-,19-/m0/s1

InChI Key

BTTWKVFKBPAFDK-LOVVWNRFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Androstane steroids

Direct Parent

Androgens and derivatives

Alternative Parents

Substituents

Androgen-skeleton
17-hydroxysteroid
3-beta-hydroxysteroid
Hydroxysteroid
3-hydroxysteroid
3-hydroxy-delta-4-steroid
Delta-4-steroid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3-hydroxy steroid (CHEBI:34386 )
Androstane and derivatives (C14210 )
C19 steroids (androgens) and derivatives (LMST02020105 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 24816252)

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0005849)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0005849)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0005849)

Source

Exogenous

Exogenous (HMDB: HMDB0005849)

Food

Food (HMDB: HMDB0005849)

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)

Endogenous

Endogenous (HMDB: HMDB0005849)

Process

Role

Biological role

Membrane stabilizer (HMDB: HMDB0005849)

Molecular messenger

Hormone (HMDB: HMDB0005849)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0005849)

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0005849)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.048 g/L	ALOGPS
logP	3.1	ALOGPS
logP	2.95	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	17.5	ChemAxon
pKa (Strongest Basic)	-0.82	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	85.33 m³·mol⁻¹	ChemAxon
Polarizability	34.38 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