(2S,3S,4S,5R,6S)-6-{4-[2-(4-{[(2S,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}phenyl)propan-2-yl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 162392
• Molecular Formular: C27H32O14
• Molecular Mass: 580.53458
• Monoisotopic Mass: 580.1792057
• SMILES: c1(C(c2ccc(cc2)O[C@@H]2O[C@H]([C@H]([C@@H]([C@@H]2O)O)O)C(=O)O)(C)C)ccc(cc1)O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)O)O)O)O
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](Oc2ccc(cc2)C(c2ccc(cc2)O[C@@H]2O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]2O)O)O)(C)C)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C27H32O14/c1-27(2,11-3-7-13(8-4-11)38-25-19(32)15(28)17(30)21(40-25)23(34)35)12-5-9-14(10-6-12)39-26-20(33)16(29)18(31)22(41-26)24(36)37/h3-10,15-22,25-26,28-33H,1-2H3,(H,34,35)(H,36,37)/t15-,16-,17-,18-,19+,20+,21-,22-,25+,26+/m0/s1
• InChIKey: ABSNOFSDPWIKPP-CQMPHNKSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-{4-[2-(4-{[(2S,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}phenyl)propan-2-yl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-{4-[2-(4-{[(2S,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}phenyl)propan-2-yl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 4,4'-(1-Methylethylidene)bisphenol Bisglucuronide; Bisphenol A Bis-(β-D-glucuronide)

Database IDs

• PubChem SID: 162256527
• PubChem CID: 71314106

CALCULATED PROPERTIES

• Acid pKa: 2.9531624
• H Acceptors: 14
• H Donor: 8
• LogD (pH = 5.5): -4.30308
• LogD (pH = 7.4): -6.7214375
• Log P: 0.1493883
• Molar Refractivity: 143.2987 cm^3
• Polarizability: 53.85449 Å^3
• Polar Surface Area: 232.9 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - B519520

A metabolite of Bisphenol A (B519495) and intermediate for B519505.