(1S,2R,10S,11S,14S,15S,17R)-14,17-dihydroxy-2,14,15-trimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-diene-4-carbaldehyde

• ChemBase ID: 1353
• Molecular Formular: C21H28O4
• Molecular Mass: 344.44462
• Monoisotopic Mass: 344.19875938
• SMILES: O[C@@]1([C@@]2([C@H]([C@H]3[C@H]([C@H](O)C2)[C@@]2(C(=CC(=O)C(=C2)C=O)CC3)C)CC1)C)C
• Canonical SMILES: O=CC1=C[C@@]2(C)C(=CC1=O)CC[C@@H]1[C@@H]2[C@H](O)C[C@]2([C@H]1CC[C@]2(C)O)C
• InChI: 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
• InChIKey: AMVODTGMYSRMNP-GNIMZFFESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10S,11S,14S,15S,17R)-14,17-dihydroxy-2,14,15-trimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-diene-4-carbaldehyde; (1S,2R,10S,11S,14S,15S,17R)-14,17-dihydroxy-2,14,15-trimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-diene-4-carbaldehyde
• IUPAC Traditional name: formebolone
• Synonyms: (11α,17β)-11,17-Dihydroxy-17-methyl-3-oxoandrosta-1,4-diene-2-carboxaldehyde; 2-Formyl-11α-hydroxy-1-methyltestosterone; 2-Formyl-17α-methylandrosta-1,4-dien-11α,17β-diol-3-one; 2-Formyl-17α-methylandrosta-1,4-diene-11α,17β-dihydroxy-3-one; 2-Formyl-17α-methylandrosta-1,4-diene-11α,17β-diol-3-one; Formebolone; Formyldienolone; Esiclene; Hubernol

Database IDs

• CAS Number: 2454-11-7
• PubChem SID: 160964813; 46508967
• PubChem CID: 17150
• Wikipedia Title: Formebolone

CALCULATED PROPERTIES

JChem

• Acid pKa: 14.39258
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.7636855
• LogD (pH = 7.4): 1.7636855
• Log P: 1.7636855
• Molar Refractivity: 96.9027 cm^3
• Polarizability: 37.39907 Å^3
• Polar Surface Area: 74.6 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.59
• LOG S: -3.76
• Solubility (Water): 6.05e-02 g/l

PROPERTIES

Physical Property

• Boiling Point: 543.6°C
• Density: 1.24 g/mL

DETAILS

DrugBank - DB01569

Drug information: illicit; experimental

Toronto Research Chemicals - F685300

This is a controlled substance (anabolic steroid). Anabolic.

REFERENCES

• De Marchi, et al.: Arzneim.-Forsch., 23, 1583 (1973)
• Masse, R., et al.: Anal. Chim. Acta, 247, 211 (1973)