(1S,2R,10S,11S,14S,15S,17S)-14,17-dihydroxy-2,8,15-trimethyl-14-(prop-1-yn-1-yl)tetracyclo[8.7.0.02,7.011,15]heptadeca-3,6,8-trien-5-one

• ChemBase ID: 153246
• Molecular Formular: C23H28O3
• Molecular Mass: 352.46662
• Monoisotopic Mass: 352.20384476
• SMILES: CC#C[C@@]1(CC[C@@H]2[C@@]1(C[C@@H]([C@H]1[C@H]2C=C(C2=CC(=O)C=C[C@]12C)C)O)C)O
• Canonical SMILES: CC#C[C@]1(O)CC[C@@H]2[C@]1(C)C[C@H](O)[C@H]1[C@H]2C=C(C2=CC(=O)C=C[C@]12C)C
• InChI: InChI=1S/C23H28O3/c1-5-8-23(26)10-7-17-16-11-14(2)18-12-15(24)6-9-21(18,3)20(16)19(25)13-22(17,23)4/h6,9,11-12,16-17,19-20,25-26H,7,10,13H2,1-4H3/t16-,17-,19-,20+,21-,22-,23-/m0/s1
• InChIKey: UFZKDKHLKHEFGA-ZFTCBNFESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10S,11S,14S,15S,17S)-14,17-dihydroxy-2,8,15-trimethyl-14-(prop-1-yn-1-yl)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6,8-trien-5-one
• IUPAC Traditional name: (1S,2R,10S,11S,14S,15S,17S)-14,17-dihydroxy-2,8,15-trimethyl-14-(prop-1-yn-1-yl)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6,8-trien-5-one
• Synonyms: (11β,17β)-11,17-Dihydroxy-6-methyl-17-(1-propynyl)-androsta-1,4,6-trien-3-one; RU 28362

Database IDs

• CAS Number: 74915-64-3
• MDL Number: MFCD03703410
• PubChem SID: 24724589; 162247385
• PubChem CID: 123790

CALCULATED PROPERTIES

• Acid pKa: 12.858536
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.9242034
• LogD (pH = 7.4): 2.924202
• Log P: 2.9242034
• Molar Refractivity: 105.4848 cm^3
• Polarizability: 39.66486 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble33 mg/mL
• Apperance: solid

Safety Information

• German water hazard class: 1
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: rat ... Nr3c1(24413)

Product Information

• Purity: ≥98% (HPLC)
• Impurities: 1.25 mol/mol Ethanol
• Empirical Formula (Hill Notation): C23H28O3

DETAILS

Sigma Aldrich - R2778

Biochem/physiol Actions
Glucocorticoid receptor agonist.