(1S,2R,10R,11S,13S,14R,15S)-13,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-6-en-5-one

• ChemBase ID: 154484
• Molecular Formular: C19H28O3
• Molecular Mass: 304.42382
• Monoisotopic Mass: 304.20384476
• SMILES: C[C@]12CCC(=O)C=C1CC[C@@H]1[C@@H]2CC[C@]2([C@H]1C[C@@H]([C@@H]2O)O)C
• Canonical SMILES: O=C1CC[C@]2(C(=C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1C[C@@H]([C@@H]2O)O)C)C
• InChI: InChI=1S/C19H28O3/c1-18-7-5-12(20)9-11(18)3-4-13-14(18)6-8-19(2)15(13)10-16(21)17(19)22/h9,13-17,21-22H,3-8,10H2,1-2H3/t13-,14+,15+,16+,17+,18+,19+/m1/s1
• InChIKey: YMCWOAZGWMZGQT-KYQPOWKGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,13S,14R,15S)-13,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• IUPAC Traditional name: (1S,2R,10R,11S,13S,14R,15S)-13,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• Synonyms: 16β,17β-Dihydroxyandrost-4-en-3-one; 4-Androstene-16β,17β-diol-3-one; 16β-Hydroxytestosterone

Database IDs

• CAS Number: 17528-90-4
• MDL Number: MFCD00271245
• PubChem SID: 162248623
• PubChem CID: 15708880

CALCULATED PROPERTIES

• Acid pKa: 13.623907
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.2905197
• LogD (pH = 7.4): 2.2905195
• Log P: 2.2905197
• Molar Refractivity: 85.7913 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: white
• Melting Point: 184-186

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
• Storage Temperature: 2-8°C

Product Information

• Empirical Formula (Hill Notation): C19H28O3

DETAILS

Sigma Aldrich - UC289

Biochem/physiol Actions
CYP3A2/2B1 (rat) metabolite; androgenic