(1S,10R,11S,15S)-15-methyl-14-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-2,4,6-trien-5-yl sulfamate

• ChemBase ID: 168276
• Molecular Formular: C18H23NO4S
• Molecular Mass: 349.44452
• Monoisotopic Mass: 349.13477922
• SMILES: c1c(cc2c(c1)[C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)(C(=O)CC2)C)OS(=O)(=O)N
• Canonical SMILES: O=C1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCc2c1ccc(c2)OS(=O)(=O)N
• InChI: InChI=1S/C18H23NO4S/c1-18-9-8-14-13-5-3-12(23-24(19,21)22)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-16H,2,4,6-9H2,1H3,(H2,19,21,22)/t14-,15-,16+,18+/m1/s1
• InChIKey: RVKFQAJIXCZXQY-CBZIJGRNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,10R,11S,15S)-15-methyl-14-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-trien-5-yl sulfamate
• IUPAC Traditional name: (1S,10R,11S,15S)-15-methyl-14-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-trien-5-yl sulfamate
• Synonyms: 3-[(Aminosulfonyl)oxy]estra-1,3,5(10)-trien-17-one; EMATE; Estrone 3-Sulfamate; Estrone O-Sulfamate; Estrone Sulfamate; Estrone 3-O-Sulfamate

Database IDs

• CAS Number: 148672-09-7
• PubChem SID: 162262408
• PubChem CID: 127676

CALCULATED PROPERTIES

• Acid pKa: 10.851216
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 3.258838
• LogD (pH = 7.4): 3.2587037
• Log P: 3.2588398
• Molar Refractivity: 90.6096 cm^3
• Polarizability: 36.162514 Å^3
• Polar Surface Area: 86.46 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 195-197°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - E889060

A potent inhibitor of estrone sulfatase. Inhibits estrone sulfatase >99% at 0.1uM in intact MCF-7 cells, IC50=65pM.

REFERENCES

• Woo, L.W., et al.: J. Med. Chem., 41, 1068 (1998)