6-oxo-6H,7H,8H,9H,10H,11H-cyclohepta[c]chromen-3-yl sulfamate

• ChemBase ID: 2038
• Molecular Formular: C14H15NO5S
• Molecular Mass: 309.3376
• Monoisotopic Mass: 309.06709359
• SMILES: S(=O)(=O)(Oc1ccc2c(c1)oc(=O)c1c2CCCCC1)N
• Canonical SMILES: O=c1oc2cc(ccc2c2c1CCCCC2)OS(=O)(=O)N
• InChI: InChI=1S/C14H15NO5S/c15-21(17,18)20-9-6-7-11-10-4-2-1-3-5-12(10)14(16)19-13(11)8-9/h6-8H,1-5H2,(H2,15,17,18)
• InChIKey: DSLPMJSGSBLWRE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-oxo-6H,7H,8H,9H,10H,11H-cyclohepta[c]chromen-3-yl sulfamate
• IUPAC Traditional name: 6-oxo-7H,8H,9H,10H,11H-cyclohepta[c]chromen-3-yl sulfamate
• Synonyms: 6-Oxo-8,9,10,11-Tetrahydro-7h-Cyclohepta[C][1]Benzopyran-3-O-Sulfamate; 667 Coumate; BN 83495; STX64

Database IDs

• CAS Number: 288628-05-7
• MDL Number: MFCD12912443
• PubChem SID: 160965493; 46507132
• PubChem CID: 5287541

CALCULATED PROPERTIES

JChem

• Acid pKa: 10.648181
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 1.9945275
• LogD (pH = 7.4): 1.994313
• Log P: 1.9945302
• Molar Refractivity: 75.6966 cm^3
• Polarizability: 30.22945 Å^3
• Polar Surface Area: 95.69 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.76
• LOG S: -3.51
• Solubility (Water): 9.67e-02 g/l

PROPERTIES

Physical Property

• Solubility: DMSO: >20 mg/mL
• Apperance: white powder

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C14H15NO5S

DETAILS

DrugBank - DB02292

Drug information: experimental

Sigma Aldrich - S1950

Biochem/physiol Actions
STX64 is a potent, irreversible inhibitor of steroid sulfatase. Inhibition of steroid sulfatase (STS), the enzyme responsible for the hydrolysis of steroid sulfates, represents a potential novel treatment for postmenopausal women with hormone-dependent breast cancer. Estrone and DHEA are formed by this sulfatase pathway and can be converted to steroids (estradiol and androstenediol, respectively), which have potent estrogenic properties. STX64 (667 coumate) is a potent tricylic coumarin-based sulfamate that irreversibly inhibits STS activity (IC50 = 8 nM in a placental microsomal assay system). Estrone sulfamate (EMATE) is also a potent STS inhibitor, but has estrogenic activity.