(1S,2R,10R,11S,12S,14S,15S)-12,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-6-en-5-one

• ChemBase ID: 153432
• 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]1[C@H](C[C@@H]2O)O)C
• Canonical SMILES: O=C1CC[C@]2(C(=C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1[C@@H](O)C[C@@H]2O)C)C
• InChI: InChI=1S/C19H28O3/c1-18-7-5-12(20)9-11(18)3-4-13-14(18)6-8-19(2)16(22)10-15(21)17(13)19/h9,13-17,21-22H,3-8,10H2,1-2H3/t13-,14+,15+,16+,17-,18+,19-/m1/s1
• InChIKey: KYGUQDTWUBBBSD-MJVYMRHDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,12S,14S,15S)-12,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• IUPAC Traditional name: 15-hydroxytestosterone
• Synonyms: (15α,17β)-15,17-Dihydroxyandrost-4-en-3-one; NSC 60794; 15α-Hydroxy Testosterone; 4-Androstene-15α,17β-diol-3-one; 15α-Hydroxytestosterone

Database IDs

• CAS Number: 2226-70-2
• MDL Number: MFCD00214301
• PubChem SID: 162247571
• PubChem CID: 247021

CALCULATED PROPERTIES

• Acid pKa: 14.409808
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.9838645
• LogD (pH = 7.4): 1.9838644
• Log P: 1.9838645
• Molar Refractivity: 85.9787 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

• Solubility: Chloroform; Ethyl Acetate
• Apperance: Off-White SOlid
• Melting Point: 195-197°C

Safety Information

• Storage Condition: Controlled Substance, -20°C Freezer
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 63-20/21/22-40
• Safety Statements: 22-36
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H332-H351-H361
• GHS Precautionary statements: P280
• 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

Toronto Research Chemicals - H956765

A metabolite of Testosterone (T155000).

REFERENCES

• Elsdale, T., et al.: J. Cell Biol., 54, 626 (1972)
• Hoogenboom, L., et al.: Xenobiotica, 19, 1207 (1972)
• Wilkening, S., et al.: Drug Metab. Dispos., 31, 1035 (1972)