14,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-6-en-5-one

• ChemBase ID: 153491
• Molecular Formular: C19H28O3
• Molecular Mass: 304.42382
• Monoisotopic Mass: 304.20384476
• SMILES: CC12CCC(=O)C=C1CCC1C2C(CC2(C1CCC2O)C)O
• Canonical SMILES: O=C1CCC2(C(=C1)CCC1C2C(O)CC2(C1CCC2O)C)C
• InChI: InChI=1S/C19H28O3/c1-18-8-7-12(20)9-11(18)3-4-13-14-5-6-16(22)19(14,2)10-15(21)17(13)18/h9,13-17,21-22H,3-8,10H2,1-2H3
• InChIKey: YQDZGFAYWGWSJK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 14,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• IUPAC Traditional name: 14,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• Synonyms: 11β,17β-Dihydroxyandrost-4-en-3-one; 4-Androstene-11β,17β-diol-3-one; 11β-Hydroxytestosterone

Database IDs

• CAS Number: 1816-85-9
• MDL Number: MFCD00010481
• PubChem SID: 162247630; 24895621
• PubChem CID: 234526

CALCULATED PROPERTIES

• Acid pKa: 14.483113
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.0566585
• LogD (pH = 7.4): 2.0566585
• Log P: 2.0566585
• Molar Refractivity: 86.0223 cm^3
• Polarizability: 33.878315 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: light yellow crystalline

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 61-40
• Safety Statements: 22-36/37/39
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H351-H360
• GHS Precautionary statements: P201-P281-P308 + P313
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• Drug Control: USDEA Schedule III; Home Office Schedule 4.2; regulated under CDSA - not available from Sigma-Aldrich Canada

Product Information

• Empirical Formula (Hill Notation): C19H28O3

DETAILS

Sigma Aldrich - H4128

Biochem/physiol Actions
Structure-activity relationships of 11-substituted testosterone derivatives as progesterone agonists, and their effect on growth and differentiation of human decidual cells.1