ChemFOnt: Showing chemical card for 7a-Hydroxytestosterone (CFc000002014)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:47 UTC

Chemfont ID

CFc000002014

Molecule Identification

Common Name

7a-Hydroxytestosterone

Definition

4-Hydroxytestosterone is the 17-hydroxylated analog to formestane. It is commercially available on the internet as anabolic steroid for oral self-administration and does not have any therapeutic indication. Hence, only little information is available about its metabolism. So far, most studies dealt with 4-hydroxytestosterone as metabolite of formestane while one study investigated the glucuronic acid conjugates of metabolic products of 4-hydroxytestosterone. This substance is prohibited in sports by the World Anti-Doping Agency; there is to a considerable increase of structurally related steroids with anabolic effects offered via the internet. 4-Hydroxytestosterone is a metabolite of the steroidal aromatase inhibitor 4-hydroxyandrost-4-ene-3,17-dione (4OHA). (PMID: 17724580 , 17610244 , 17207827 , 1284430 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(17beta)-4,17-Dihydroxy-androst-4-en-3-one	HMDB
(3b,17a)-Androst-5-ene-3,17-diol	HMDB
3b,17a-Dihydroxyandrost-5-ene	HMDB
4,17beta-Dihydroxy-4-androstene-3-one	HMDB
4-Androstene-7alpha-17beta-diol-3-one	HMDB
4-OHT	HMDB
7alpha-Hydroxytestosterone	HMDB
Androst-5-ene-3b,17a-diol	HMDB
D5-Androstene-3b,17a-diol	HMDB
4,17 beta-Dihydroxy-4-androstene-3-one	MeSH, HMDB

Chemical Formula

C₁₉H₂₈O₃

Average Molecular Weight

304.4238

Monoisotopic Molecular Weight

304.203844762

IUPAC Name

(2R,14S,15S)-6,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

Traditional Name

(2R,14S,15S)-6,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

CAS Registry Number

2141-17-5

SMILES

C[C@]12CCC3C(CCC4=C(O)C(=O)CC[C@]34C)C1CC[C@@H]2O

InChI Identifier

InChI=1S/C19H28O3/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/h11-13,16,21-22H,3-10H2,1-2H3/t11?,12?,13?,16-,18+,19-/m0/s1

InChI Key

BQOIJSIMMIDHMO-XRJYYLNASA-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
4-hydroxysteroid
Hydroxysteroid
Oxosteroid
17-hydroxysteroid
Delta-4-steroid
Cyclohexenone
Cyclic alcohol
Ketone
Secondary alcohol
Cyclic ketone
Enol
Organic oxygen compound
Organooxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0003956)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0003956)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0003956)

Source

Exogenous

Exogenous (HMDB: HMDB0003956)

Food

Food (HMDB: HMDB0003956)

Process

Role

Biological role

Membrane stabilizer (HMDB: HMDB0003956)

Molecular messenger

Hormone (HMDB: HMDB0003956)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0003956)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.068 g/L	ALOGPS
logP	2.48	ALOGPS
logP	2.85	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	9.28	ChemAxon
pKa (Strongest Basic)	-0.88	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	86.4 m³·mol⁻¹	ChemAxon
Polarizability	34.89 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

External Links

HMDB ID

HMDB0003956

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023273

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C05291

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53477776

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Camerino, Bruno; Patelli, Bianca; Sciaky, Roberto. 4-Hydroxy steroids. (1962), 4 pp.

Showing chemical card for 7a-Hydroxytestosterone (CFc000002014)

MOL for CFc000002014 (7a-Hydroxytestosterone)

3D MOL for CFc000002014 (7a-Hydroxytestosterone)

3D SDF for CFc000002014 (7a-Hydroxytestosterone)

3D-SDF for CFc000002014 (7a-Hydroxytestosterone)

PDB for CFc000002014 (7a-Hydroxytestosterone)

3D PDB for CFc000002014 (7a-Hydroxytestosterone)

SMILES for CFc000002014 (7a-Hydroxytestosterone)

INCHI for CFc000002014 (7a-Hydroxytestosterone)

Structure for CFc000002014 (7a-Hydroxytestosterone)

3D Structure for CFc000002014 (7a-Hydroxytestosterone)