(1S,2R,10R,11S,14R,15S)-14-acetyl-2,8,15-trimethyl-13-methylidene-5-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-6,8-dien-14-yl (2H3)acetate

• ChemBase ID: 172619
• Molecular Formular: C25H32O4
• Molecular Mass: 396.51918
• Monoisotopic Mass: 396.2300595
• SMILES: C1C(=O)C=C2[C@](C1)([C@@H]1[C@@H](C=C2C)[C@H]2[C@](CC1)([C@@](C(=C)C2)(OC(=O)C)C(=O)C)C)C
• Canonical SMILES: O=C1CC[C@]2(C(=C1)C(=C[C@@H]1[C@@H]2CC[C@]2([C@H]1CC(=C)[C@]2(OC(=O)C)C(=O)C)C)C)C
• InChI: InChI=1S/C25H32O4/c1-14-11-19-20(23(5)9-7-18(28)13-21(14)23)8-10-24(6)22(19)12-15(2)25(24,16(3)26)29-17(4)27/h11,13,19-20,22H,2,7-10,12H2,1,3-6H3/t19-,20+,22+,23-,24+,25+/m1/s1
• InChIKey: UDKABVSQKJNZBH-DWNQPYOZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,14R,15S)-14-acetyl-2,8,15-trimethyl-13-methylidene-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-6,8-dien-14-yl (^2H₃)acetate
• IUPAC Traditional name: (1S,2R,10R,11S,14R,15S)-14-acetyl-2,8,15-trimethyl-13-methylidene-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-6,8-dien-14-yl (^2H₃)acetate
• Synonyms: 17-(Acetyloxy-d3)-6-methyl-16-methylenepregna-4,6-diene-3,20-dione; 17-Hydroxy-6-methyl-16-methylenepregna-4,6-diene-3,20-dione Acetate-d3; 17-(Acetoxy-d3)-6-methyl-16-methylenepregna-4,6-diene-3,20-dione; 6-Dehydro-16-methylene-17α-hydroxy-6α-methylprogesterone Acetate-d3; Heifermax 500-d3; NSC-70968-d3; Melengestrol Acetate-d3

Database IDs

• PubChem SID: 164228529
• PubChem CID: 71749941

CALCULATED PROPERTIES

• Acid pKa: 17.536983
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 3.819025
• LogD (pH = 7.4): 3.819025
• Log P: 3.819025
• Molar Refractivity: 112.8275 cm^3
• Polarizability: 44.043472 Å^3
• Polar Surface Area: 60.44 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 218-220°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - M215352

Labelled Melengestrol acetate (M215352). Orally active progestational steroid. Progestogen; growth promotant.

REFERENCES

• Patton, M., et al.: Zoo Biol., 26, 311(2007)
• Sellin, M., et al.: Environ. Toxicol. Chem., 28, 2443 (2007)
• Fliri, A., et al.: J. Med. Chem., 52, 8038 (2007)
• Sanseverino, J., et al.: Toxicol. Sci., 107, 122 (2007)