(1S,2R,4R,10R,11S,14S,15S)-4,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-6-en-5-one

• ChemBase ID: 153470
• Molecular Formular: C19H28O3
• Molecular Mass: 304.42382
• Monoisotopic Mass: 304.20384476
• SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC1=CC(=O)[C@@H](C[C@]31C)O
• Canonical SMILES: O=C1C=C2CC[C@@H]3[C@@H]([C@]2(C[C@H]1O)C)CC[C@]1([C@H]3CC[C@@H]1O)C
• InChI: InChI=1S/C19H28O3/c1-18-8-7-14-12(13(18)5-6-17(18)22)4-3-11-9-15(20)16(21)10-19(11,14)2/h9,12-14,16-17,21-22H,3-8,10H2,1-2H3/t12-,13-,14-,16+,17-,18-,19-/m0/s1
• InChIKey: ZOIPFFUVGMVQGE-DTQPDNRZSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 4075-14-3
• MDL Number: MFCD00132939
• PubChem SID: 24895535; 162247609
• PubChem CID: 14311666

CALCULATED PROPERTIES

• Acid pKa: 13.384813
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.4943573
• LogD (pH = 7.4): 2.4943569
• Log P: 2.4943573
• Molar Refractivity: 85.922 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; Methanol
• Apperance: White Solid
• Melting Point: 162-165°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

Product Information

• Purity: ≥97%
• Empirical Formula (Hill Notation): C19H28O3

DETAILS

Sigma Aldrich - H2773

Biochem/physiol Actions
Testosterone metabolite

Toronto Research Chemicals - H956740

A metabolite of Testosterone (T155000) in human. Controlled substance.

REFERENCES

• Seckl, J., et al.: Steroids, 62, 89 (1997)
• Reynolds, R., et al.: J. Clin. Endocrinol. Metab., 86, 245 (1997)
• Wolf, C., et al.: Toxicol. Sci. 65, 71 (1997)
• Borlak, J., et al.: Drug Metab. Dispos., 32, 675 (1997)