(1S,2R,10R,14R,15S)-15-ethyl-14-ethynyl-14-hydroxy(2,4,4,6,8,8-2H6)tetracyclo[8.7.0.02,7.011,15]heptadeca-6,12-dien-5-one

• ChemBase ID: 169621
• Molecular Formular: C21H26O2
• Molecular Mass: 310.42994
• Monoisotopic Mass: 310.19328007
• SMILES: C1CC(=O)C=C2[C@H]1[C@@H]1[C@@H](CC2)C2[C@](CC1)([C@](C=C2)(O)C#C)CC
• Canonical SMILES: C#C[C@]1(O)C=CC2[C@]1(CC)CC[C@H]1[C@H]2CCC2=CC(=O)CC[C@H]12
• InChI: InChI=1S/C21H26O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,10,12-13,16-19,23H,3,5-9,11H2,1H3/t16?,17-,18-,19?,20+,21+/m1/s1
• InChIKey: SIGSPDASOTUPFS-XGGDNPRESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,14R,15S)-15-ethyl-14-ethynyl-14-hydroxy(2,4,4,6,8,8-^2H₆)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-6,12-dien-5-one
• IUPAC Traditional name: (1S,2R,10R,14R,15S)-15-ethyl-14-ethynyl-14-hydroxy(2,4,4,6,8,8-^2H₆)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-6,12-dien-5-one
• Synonyms: (17α)-13-Ethyl-17-hydroxy-18,19-dinorpregna-4,15-dien-20-yn-3-one-d6; SH B 331-d6; Gestodene-d6

Database IDs

• PubChem SID: 162263753
• PubChem CID: 46780428

CALCULATED PROPERTIES

• LogD (pH = 7.4): 3.4557824
• Log P: 3.4557824
• Molar Refractivity: 92.9881 cm^3
• Polarizability: 35.607704 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true
• Acid pKa: 17.083544
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.4557824

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate
• Apperance: Pale Yellow Solid
• Melting Point: 200-202°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - G368252

Labelled Gestodene. Orally active gestogen with progesterone-like profile of activity. Used in combination with estrogen as oral contraceptive.

REFERENCES

• Duesterberg, B., et al.: Contraception, 24, 673 (1981)
• Duesterberg, B., et al.: Seroids, 43, 43 (1981)
• Losert, W., et al.: Arzneim.-Forsch., 35, 459 (1981)