(1S,2R,10S,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-6-ene-5,17-dione

• ChemBase ID: 132238
• Molecular Formular: C19H26O3
• Molecular Mass: 302.40794
• Monoisotopic Mass: 302.18819469
• SMILES: C[C@]12CCC(=O)C=C1CC[C@@H]1[C@@H]2C(=O)C[C@]2([C@H]1CC[C@@H]2O)C
• Canonical SMILES: O=C1CC[C@]2(C(=C1)CC[C@@H]1[C@@H]2C(=O)C[C@]2([C@H]1CC[C@@H]2O)C)C
• InChI: InChI=1S/C19H26O3/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/h9,13-14,16-17,22H,3-8,10H2,1-2H3/t13-,14-,16-,17+,18-,19-/m0/s1
• InChIKey: WTPMRQZHJLJSBO-XQALERBDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10S,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-ene-5,17-dione
• IUPAC Traditional name: 11-ketotestosterone
• Synonyms: 17β-Hydroxy-4-androstene-3,11-dione; 17β-Hydroxyandrost-4-ene-3,11-dione; 4-Androsten-17β-ol-3,11-dione; 11-Ketotestosterone; (17β)-17-Hydroxyandrost-4-ene-3,11-dione; 11-Ketotestosterone; 11-Oxotestosterone; 11-Keto Testosterone

Database IDs

• CAS Number: 564-35-2
• MDL Number: MFCD00198520
• PubChem SID: 24896245; 162226515
• PubChem CID: 5282365

CALCULATED PROPERTIES

• Acid pKa: 14.686659
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.4421728
• LogD (pH = 7.4): 2.4421728
• Log P: 2.4421728
• Molar Refractivity: 85.0971 cm^3
• Polarizability: 33.33251 Å^3
• Polar Surface Area: 54.37 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Drug Control: USDEA Schedule III; Home Office Schedule 4.2; regulated under CDSA - not available from Sigma-Aldrich Canada

DETAILS

Sigma Aldrich - K8250

Biochem/physiol Actions
11-Ketotestosterone is a minor androgen in humans, but a major androgen in fish.

Toronto Research Chemicals - K287000

A metabolite of Adrenosterone.

REFERENCES

• Basit, A., et al.: Int. J. Pharm., 237, 23 (2002)
• Basit, A., et al.: Int. J. Pharm., 237, 23 (2002)
• Arosh, J., et al.: Endocrinology, 145, 2551 (2002)