(1S,3'R,4'S,5'S,6'R)-6-[(4-ethylphenyl)methyl]-6'-(hydroxymethyl)-3H-spiro[2-benzofuran-1,2'-oxane]-3',4',5'-triol

• ChemBase ID: 178692
• Molecular Formular: C22H26O6
• Molecular Mass: 386.43824
• Monoisotopic Mass: 386.17293855
• SMILES: c1c(ccc(c1)Cc1ccc2c(c1)[C@]1(OC2)O[C@@H]([C@H]([C@@H]([C@H]1O)O)O)CO)CC
• Canonical SMILES: OC[C@H]1O[C@]2(OCc3c2cc(cc3)Cc2ccc(cc2)CC)[C@@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C22H26O6/c1-2-13-3-5-14(6-4-13)9-15-7-8-16-12-27-22(17(16)10-15)21(26)20(25)19(24)18(11-23)28-22/h3-8,10,18-21,23-26H,2,9,11-12H2,1H3/t18-,19-,20+,21-,22+/m1/s1
• InChIKey: VWVKUNOPTJGDOB-BDHVOXNPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,3'R,4'S,5'S,6'R)-6-[(4-ethylphenyl)methyl]-6'-(hydroxymethyl)-3H-spiro[2-benzofuran-1,2'-oxane]-3',4',5'-triol
• IUPAC Traditional name: (1S,3'R,4'S,5'S,6'R)-6-[(4-ethylphenyl)methyl]-6'-(hydroxymethyl)-3H-spiro[2-benzofuran-1,2'-oxane]-3',4',5'-triol
• Synonyms: CSG 452; Tofogliflozin; (1S,3'R,4'S,5'S,6'R)-6-[(4-Ethylphenyl)methyl]-3',4',5',6'-tetrahydro-6'-(hydroxymethyl)spiro[isobenzofuran-1(3H),2'-[2H]pyran]-3',4',5'-triol

Database IDs

• CAS Number: 903565-83-3
• PubChem SID: 164234602
• PubChem CID: 46908929

CALCULATED PROPERTIES

• Acid pKa: 12.001273
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 2.4703786
• LogD (pH = 7.4): 2.470368
• Log P: 2.4703786
• Molar Refractivity: 103.3288 cm^3
• Polarizability: 40.591362 Å^3
• Polar Surface Area: 99.38 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T528750

A novel, potent, and highly selective SGLT2 inhibitor that has been shown to improve glycemic control in diabetic mice and rats.