ContaminantDB: Formebolone

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-26 05:59:29 UTC

Update Date

2026-04-13 20:58:06 UTC

Accession Number

CHEM035689

Identification

Common Name

Formebolone

Class

Small Molecule

Description

Formebolone, a derivative of androstane, is an anabolic androgenic steroid. It is on the list of substances prohibited by the Word Anti-Doping Agency, and is regularly screened for in athletes.[A14416] It is also classified by the US Drug Enforcement Administration as Schedule III drug in the Controlled Substances Act. It has been used experimentally in the treatment of growth retardation, and has been noted to increase bone mass.[A14416] Additionally, it has been patented for use in development of novel transdermal delivery systems for enhanced drug delivery.

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(11a,17b)-11,17-Dihydroxy-17-methyl-3-oxo-androsta-1,4-diene-2-carboxaldehyde	HMDB
11a,17b-Dihydroxy-17-methyl-3-oxo-androsta-1,4-diene-2-carboxaldehyde	HMDB
11a,17b-Dihydroxy-17-methyl-3-oxoandrosta-1,4-diene-2-carboxaldehyde	HMDB
2-Formyl-11a-hydroxy-D1-methyltestosterone	HMDB
2-Formyl-17a-methylandrosta-1,4-dien-11a,17b-diol-3-one	HMDB
2-Formyl-17a-methylandrosta-1,4-diene-11a,17b-dihydroxy-3-one	HMDB
2-Formyl-17a-methylandrosta-1,4-diene-11a,17b-diol-3-one	HMDB
Esiclene	HMDB, MeSH
Formyldienolone	HMDB, MeSH
2-Formyl-17 alpha-methylandrosta-1,4-diene-11 alpha,17 beta-diol-3-one	MeSH, HMDB
Formyldienolone, (11 beta,17beta)-isomer	MeSH, HMDB
Formildienolone	MeSH, HMDB
Formebolone	MeSH

Chemical Formula

C₂₁H₂₈O₄

Average Molecular Mass

344.445 g/mol

Monoisotopic Mass

344.199 g/mol

CAS Registry Number

2454-11-7

IUPAC Name

(1S,2R,10S,11S,14S,15S,17R)-14,17-dihydroxy-2,14,15-trimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-diene-4-carbaldehyde

Traditional Name

formebolone

SMILES

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

InChI Identifier

InChI=1S/C21H28O4/c1-19-9-12(11-22)16(23)8-13(19)4-5-14-15-6-7-21(3,25)20(15,2)10-17(24)18(14)19/h8-9,11,14-15,17-18,24-25H,4-7,10H2,1-3H3/t14-,15-,17+,18+,19-,20-,21-/m0/s1

InChI Key

AMVODTGMYSRMNP-GNIMZFFESA-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-1,4-steroid
3-oxosteroid
Hydroxysteroid
Oxosteroid
11-alpha-hydroxysteroid
11-hydroxysteroid
17-hydroxysteroid
Delta-1,4-steroid
Cyclic alcohol
Tertiary alcohol
Secondary alcohol
Ketone
Cyclic ketone
Aldehyde
Organooxygen compound
Alcohol
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

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	0.06 g/L	ALOGPS
logP	2.59	ALOGPS
logP	1.76	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	14.39	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	96.9 m³·mol⁻¹	ChemAxon
Polarizability	38.13 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	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	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00or-1549000000-42102185d1dded40ecea	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00di-3506900000-e9c4f9b646ae0846ac95	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-056r-0009000000-83d05b9ec6d4114e8a0c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a6r-0239000000-e2958d7b5f276c7c8f72	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0rkd-2294000000-a7c54e1065ffa26a8568	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0009000000-be5664450200906ba6e6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002f-0009000000-51507deb2305cd3590af	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01ta-1196000000-a3d80644f38949e4fd48	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0009000000-132e2debff844207d185	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0019000000-440aecd91bd6be86b2b4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-0293000000-688a79dea37f10a0d946	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002b-0019000000-4d6ca44432cd0e2ca971	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000e-3954000000-ac54633877d9786e5126	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-4890000000-b21d6e58b198bff27fda	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB01569

HMDB ID

HMDB0004631

FooDB ID

FDB023388

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Formebolone

Chemspider ID

16234

ChEBI ID

Not Available

PubChem Compound ID

17150

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Canonica, Luigi; Jommi, Giancarlo; Pelizzoni, Francesca; Scolastico, Carlo. 1,11-Oxido steroids. I. 1a,11a-Oxidoandrostanes. Gazzetta Chimica Italiana (1965), 95(3), 138-50.

2. Canonica, Luigi; Jommi, Giancarlo; Pelizzoni, Francesca; Scolastico, Carlo. 1,11-Oxido steroids. I. 1a,11a-Oxidoandrostanes. Gazzetta Chimica Italiana (1965), 95(3), 138-50.

3. Thevis M, Schanzer W: Examples of doping control analysis by liquid chromatography-tandem mass spectrometry: ephedrines, beta-receptor blocking agents, diuretics, sympathomimetics, and cross-linked hemoglobins. J Chromatogr Sci. 2005 Jan;43(1):22-31.

Formebolone (CHEM035689)

Structure for CHEM035689: Formebolone