(1S,2R,8S,10R,11S,14R,15S)-14-acetyl-14-hydroxy-2,8,15-trimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-5-one

• ChemBase ID: 172605
• Molecular Formular: C22H30O3
• Molecular Mass: 342.4718
• Monoisotopic Mass: 342.21949482
• SMILES: [C@@]12(C(=CC(=O)C=C2)[C@H](C[C@@H]2[C@@H]1CC[C@]1([C@H]2CC[C@@]1(C(=O)C)O)C)C)C
• Canonical SMILES: O=C1C=C[C@]2(C(=C1)[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@]2(O)C(=O)C)C)C
• InChI: InChI=1S/C22H30O3/c1-13-11-16-17(20(3)8-5-15(24)12-19(13)20)6-9-21(4)18(16)7-10-22(21,25)14(2)23/h5,8,12-13,16-18,25H,6-7,9-11H2,1-4H3/t13-,16+,17-,18-,20+,21-,22-/m0/s1
• InChIKey: QHEQDIOZYZOPKF-HBNHAYAOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,8S,10R,11S,14R,15S)-14-acetyl-14-hydroxy-2,8,15-trimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one
• IUPAC Traditional name: (1S,2R,8S,10R,11S,14R,15S)-14-acetyl-14-hydroxy-2,8,15-trimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one
• Synonyms: (6α)-17-Hydroxy-6-methylpregna-1,4-diene-3,20-dione; 17-Hydroxy-6α-methyl-Pregna-1,4-diene-3,20-dione; 1-Dehydromedroxyprogesterone; Δ1-Medroxy Progesterone

Database IDs

• CAS Number: 3660-13-7
• PubChem SID: 164228515
• PubChem CID: 15085844

CALCULATED PROPERTIES

• Acid pKa: 12.699646
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.6860218
• LogD (pH = 7.4): 3.6860197
• Log P: 3.6860218
• Molar Refractivity: 99.7472 cm^3
• Polarizability: 38.614105 Å^3
• Polar Surface Area: 54.37 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M203565

Δ1-Medroxy Progesterone is a 1,2-dehydro derivative of Medroxy Progesterone (M203550). Δ1-Medroxy Progesterone showed antiinflammatory activity in eye inflammation.

REFERENCES

• De Ruggieri, P. et al.: Farm. Ed. Sci., 31, 849 (1976)