4-Hydroxyandrostenedione (CED0010336)

Record Information

Version

1.0

Creation Date

2016-05-22 04:19:22 UTC

Update Date

2026-05-14 19:00:35 UTC

Accession Number

CHEM017414

Identification

Common Name

4-Hydroxyandrostenedione

Class

Small Molecule

Description

4-Hydroxyandrostenedione (C19H26O3) is an organic compound with an average molecular weight of 302.41 g/mol. 4-Hydroxyandrostenedione belongs to the androstane steroids, a subclass of steroids and steroid derivatives within the organic compounds. In terms of biochemical activity, the compound is recorded as an inhibitor of the protein target Aromatase (CYP19A1). The compound is found in or released from ten recorded sources across several categories. Within the healthcare, pharmaceuticals, and veterinary products sector, it is associated with hormone antagonists and related agents. In food, food processing, and cookware, it is linked to the processing of fish. It is also found in household cleaning and consumer products, specifically within soap detergents, perfumes within detergents and soaps, tobacco smoke filters, and non-electric simulated smoking devices. Additionally, it is present in electrical and electronic equipment, including radio transmission systems, electric switches, selectors, and electrically stimulated smoking devices. The recorded route of exposure for 4-Hydroxyandrostenedione is intramuscular.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
4-Hydroxy-4-androstene-3,17-dione	ChEBI
4-Hydroxy-Delta(4)-androstenedione	ChEBI
4-Hydroxyandrostenedione	ChEBI
4-OH-a	ChEBI
4-OHAD	ChEBI
CGP 32349	ChEBI
CGP-32349	ChEBI
Formestano	ChEBI
Formestanum	ChEBI
Lentaron	ChEBI
4-Hydroxy-δ(4)-androstenedione	Generator
4-Hydroxyandrost-4-ene-3,17-dione	MeSH
4-Hydroxyandrostene-3,17-dione	MeSH
4-OHA	MeSH

Chemical Formula

C₁₉H₂₆O₃

Average Molecular Mass

302.408 g/mol

Monoisotopic Mass

302.188 g/mol

CAS Registry Number

566-48-3

IUPAC Name

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

Traditional Name

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

SMILES

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

InChI Identifier

InChI=1S/C19H26O3/c1-18-10-8-15(20)17(22)14(18)4-3-11-12-5-6-16(21)19(12,2)9-7-13(11)18/h11-13,22H,3-10H2,1-2H3/t11-,12-,13-,18+,19-/m0/s1

InChI Key

OSVMTWJCGUFAOD-KZQROQTASA-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
3-oxo-delta-4-steroid
3-oxosteroid
Oxosteroid
17-oxosteroid
4-hydroxysteroid
Hydroxysteroid
Delta-4-steroid
Cyclohexenone
Cyclic ketone
Ketone
Enol
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

enol (CHEBI:75172 )
3-oxo Delta(4)-steroid (CHEBI:75172 )
17-oxo steroid (CHEBI:75172 )
hydroxy steroid (CHEBI:75172 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.058 g/L	ALOGPS
logP	2.57	ALOGPS
logP	3.41	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	9.21	ChemAxon
pKa (Strongest Basic)	-3.7	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	0	ChemAxon
Refractivity	85.57 m³·mol⁻¹	ChemAxon
Polarizability	34.07 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-00dj-0290000000-9e0e8c02932ef9955cd2	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-01t9-2920000000-24696d73561fe3ce6680	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-0149000000-11d805d0bb7b589185bb	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0zmr-0392000000-f8aaf769dca42c4d9223	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0uxs-6980000000-3487a84fd6a5a6a92bd9	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-0009000000-39d7e8f79ca0a3ccdc3a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-0029000000-508846fbffaab39af2b2	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0076-2090000000-b52e88a46c3767f31038	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
2798.0	Log mg/kg	[1600:5000]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
360	Hormone antagonists and related agents	Healthcare, pharmaceuticals & veterinary products	Not Available
517	Electric Switches	Electrical & Electronic Equipment	Not Available
518	Electrically Stimulated Smoking Devices	Electrical & Electronic Equipment	Not Available
530	Radio Transmission Systems	Electrical & Electronic Equipment	Not Available
532	Selectors	Electrical & Electronic Equipment	Not Available
551	Processing Fish	Food, food processing & cookware	Not Available
559	Non Electric Simulated Smoking Devices	Household cleaning & consumer products	Not Available
561	Perfumes Within Detergents And Soaps	Household cleaning & consumer products	Not Available
563	Soap Detergents	Household cleaning & consumer products	Not Available
569	Tobacco Smoke Filters	Household cleaning & consumer products	Not Available
580	Manufacture Preparation Of Tobacco Products	Industrial manufacturing & chemical processing	Not Available
591	Lifeboats	Marine, shipping & aquaculture	Not Available
592	Marine Propulsion Or Steering	Marine, shipping & aquaculture	Not Available
609	Aftershave	Personal care & cosmetics	Not Available
610	Aftersun Products	Personal care & cosmetics	Not Available
611	Anti Perspirants Or Body Deoderants	Personal care & cosmetics	Not Available
614	Essential Oils Or Perfumes	Personal care & cosmetics	Not Available
615	Eye Makeup Products	Personal care & cosmetics	Not Available
617	Lip Care Products	Personal care & cosmetics	Not Available
618	Lip Makeup Products	Personal care & cosmetics	Not Available
620	Card Games	Recreation & sports surfaces	Not Available
632	Apparel	Textiles, leather & furnishings	Not Available
652	Ropes	Textiles, leather & furnishings	Not Available
662	Yarns Or Threads	Textiles, leather & furnishings	Not Available

Pathways

1 pathway

Formestane Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Sex hormone-binding globulin	P04278	Humans	Predicted (SEA)	3.26967
Click to view 3D structure	Corticosteroid-binding globulin	P08185	Humans	Predicted (SEA)	2.33548
Click to view 3D structure	Glucose-6-phosphate 1-dehydrogenase	Q9GRG7	Trypanosoma brucei	Predicted (SEA)	0.467095
Click to view 3D structure	Aromatase	P11511	Humans	Predicted (SEA)	5.60514
Click to view 3D structure	G-protein coupled bile acid receptor 1	Q8TDU6	Humans	Predicted (SEA)	11.2881
Click to view 3D structure	Androgen receptor	P15207	Rattus norvegicus	Predicted (SEA)	5.83869
Click to view 3D structure	Estrogen receptor	P03372	Humans	Predicted (SEA)	25.6902
Click to view 3D structure	Progesterone receptor	Q690N0	Bos taurus	Predicted (SEA)	5.60514
Click to view 3D structure	Aldo-keto reductase family 1 member B10	O60218	Humans	Predicted (SEA)	8.95266
Click to view 3D structure	17-beta-hydroxysteroid dehydrogenase type 1	P14061	Humans	Predicted (SEA)	7.16213
Click to view 3D structure	Sulfotransferase 1E1	P19217	Bos taurus	Predicted (SEA)	0.233548
Click to view 3D structure	Glucocorticoid receptor	P04150	Humans	Predicted (SEA)	22.3427
Click to view 3D structure	Androgen receptor	P10275	Humans	Predicted (SEA)	30.2833
Click to view 3D structure	Estrogen receptor beta	Q92731	Humans	Predicted (SEA)	36.2777
Click to view 3D structure	Progesterone receptor	P06401	Humans	Predicted (SEA)	30.2055
Click to view 3D structure	Mineralocorticoid receptor	P08235	Humans	Predicted (SEA)	22.6541
Click to view 3D structure	17-beta-hydroxysteroid dehydrogenase type 3	O54939	Rattus norvegicus	Predicted (SEA)	0.700643
Click to view 3D structure	Androgen receptor	P19091	Mus musculus	Predicted (SEA)	6.30579
Click to view 3D structure	Steroid 17-alpha-hydroxylase/17,20 lyase	P05093	Humans	Predicted (SEA)	16.3483
Click to view 3D structure	Steryl-sulfatase	P08842	Humans	Predicted (SEA)	5.0602
Click to view 3D structure	Solute carrier organic anion transporter family member 1A1	P46720	Rattus norvegicus	Predicted (SEA)	6.61718
Click to view 3D structure	3-oxo-5-alpha-steroid 4-dehydrogenase 2	P31213	Humans	Predicted (SEA)	7.31783
Click to view 3D structure	Gamma-aminobutyric acid receptor subunit alpha-4	P28471	Rattus norvegicus	Predicted (SEA)	0.467095
Click to view 3D structure	17-beta-hydroxysteroid dehydrogenase type 3	P37058	Humans	Predicted (SEA)	3.19182
Click to view 3D structure	Glucose-6-phosphate 1-dehydrogenase	P11413	Humans	Predicted (SEA)	1.79053