(1S,2R,10R,11S,14R,15S)-2,15-dimethyl-8-methylidene-5-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-14-yl sulfamate

• ChemBase ID: 170511
• Molecular Formular: C20H27NO4S
• Molecular Mass: 377.49768
• Monoisotopic Mass: 377.16607935
• SMILES: C1=CC(=O)C=C2[C@]1([C@@H]1[C@@H](CC2=C)[C@H]2[C@](CC1)([C@@H](CC2)OS(=O)(=O)N)C)C
• Canonical SMILES: O=C1C=C[C@]2(C(=C1)C(=C)C[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@H]2OS(=O)(=O)N)C)C
• InChI: InChI=1S/C20H27NO4S/c1-12-10-14-15-4-5-18(25-26(21,23)24)20(15,3)9-7-16(14)19(2)8-6-13(22)11-17(12)19/h6,8,11,14-16,18H,1,4-5,7,9-10H2,2-3H3,(H2,21,23,24)/t14-,15-,16-,18+,19+,20-/m0/s1
• InChIKey: BXBPPIUOJFDEQT-CNFQODSWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,14R,15S)-2,15-dimethyl-8-methylidene-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl sulfamate
• IUPAC Traditional name: (1S,2R,10R,11S,14R,15S)-2,15-dimethyl-8-methylidene-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl sulfamate
• Synonyms: (17β)-17-[(Aminosulfonyl)oxy]-6-methyleneandrosta-1,4-dien-3-one; 17β-Hydroxy Exemestane Sulfonylamide; Methylene Boldenone Sulfamate,; 17β-Hydroxy Exemestane Sulfamate

Database IDs

• PubChem SID: 164226421
• PubChem CID: 71749002

CALCULATED PROPERTIES

• Acid pKa: 10.840841
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.7827282
• LogD (pH = 7.4): 2.7825904
• Log P: 2.7827299
• Molar Refractivity: 101.3764 cm^3
• Polarizability: 40.01707 Å^3
• Polar Surface Area: 86.46 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H942345

17β-Hydroxy Exemestane Sulfamate is a metabolite of Exemestane (E957000).

REFERENCES

• Nicola, M.H., et al.: J. Med. Chem., 37, 219 (1994)
• Sigfrid, S., et al.: Steroids, 61, 710 (1994)