(1R,2S,3S,5S,7S,10S,11R,14S,16R)-14,16-dihydroxy-7,11-dimethylpentacyclo[8.8.0.02,7.03,5.011,16]octadec-17-en-6-one

• ChemBase ID: 167834
• Molecular Formular: C20H28O3
• Molecular Mass: 316.43452
• Monoisotopic Mass: 316.20384476
• SMILES: C1[C@@H](C[C@@]2([C@](C1)([C@@H]1[C@@H](C=C2)[C@H]2[C@](CC1)(C(=O)[C@@H]1[C@H]2C1)C)C)O)O
• Canonical SMILES: O[C@H]1CC[C@]2([C@](C1)(O)C=C[C@@H]1[C@@H]2CC[C@]2([C@H]1[C@@H]1C[C@@H]1C2=O)C)C
• InChI: InChI=1S/C20H28O3/c1-18-6-5-15-12(16(18)13-9-14(13)17(18)22)4-8-20(23)10-11(21)3-7-19(15,20)2/h4,8,11-16,21,23H,3,5-7,9-10H2,1-2H3/t11-,12+,13+,14-,15-,16+,18-,19+,20-/m0/s1
• InChIKey: IYCDFUCBUZDDIU-MBYPHNFESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,3S,5S,7S,10S,11R,14S,16R)-14,16-dihydroxy-7,11-dimethylpentacyclo[8.8.0.0^2,^7.0^3,^5.0^1^1,^1^6]octadec-17-en-6-one
• IUPAC Traditional name: (1R,2S,3S,5S,7S,10S,11R,14S,16R)-14,16-dihydroxy-7,11-dimethylpentacyclo[8.8.0.0^2,^7.0^3,^5.0^1^1,^1^6]octadec-17-en-6-one
• Synonyms: (3β,5β,15α,16α)-15,16-Dihydro-3,5-dihydroxy-3'H-cycloprop[15,16]androsta-6,15-dien-17-one; 15β,16β-Methylene-3β,5β-dihydroxyandrost-6-en-17-one; 3β,5-Dihydroxy-15β,16β-methylene-5β-androst-6-en-17-one

Database IDs

• CAS Number: 82543-15-5
• PubChem SID: 162261967
• PubChem CID: 13075974

CALCULATED PROPERTIES

• Acid pKa: 13.875491
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.2508874
• LogD (pH = 7.4): 2.2508872
• Log P: 2.2508874
• Molar Refractivity: 88.9759 cm^3
• Polarizability: 34.992188 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid
• Melting Point: 199-203°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - D453200

An impurity of the synthetic progestogen Drospirenone (D453200). It is used in the preparation of aldosterone antagonists.