5-[(2S,3S)-4-{2-[(2R,3S)-3-[(2S,3S)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-yl]ethenyl}-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol

• ChemBase ID: 130165
• Molecular Formular: C56H42O12
• Molecular Mass: 906.92548
• Monoisotopic Mass: 906.26762678
• SMILES: Oc1ccc(cc1)[C@H]1Oc2c([C@@H]1c1cc(O)cc(O)c1)c(cc(c2)O)/C=C/c1cc2[C@H](c3c4[C@H](c5cc(O)cc(O)c5)[C@@H](c5ccc(O)cc5)Oc4cc(O)c3)[C@H](c3ccc(O)cc3)Oc2cc1
• Canonical SMILES: Oc1ccc(cc1)[C@@H]1Oc2c([C@@H]1c1cc(O)cc3c1[C@H](c1cc(O)cc(c1)O)[C@H](O3)c1ccc(cc1)O)cc(cc2)/C=C/c1cc(O)cc2c1[C@H](c1cc(O)cc(c1)O)[C@H](O2)c1ccc(cc1)O
• InChI: InChI=1S/C56H42O12/c57-35-10-4-29(5-11-35)54-50(33-19-38(60)23-39(61)20-33)49-32(18-42(64)26-47(49)67-54)3-1-28-2-16-46-44(17-28)52(56(66-46)31-8-14-37(59)15-9-31)45-25-43(65)27-48-53(45)51(34-21-40(62)24-41(63)22-34)55(68-48)30-6-12-36(58)13-7-30/h1-27,50-52,54-65H/t50-,51-,52+,54+,55+,56-/m0/s1
• InChIKey: WZKKRZSJTLGPHH-YOSVHTRQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[(2S,3S)-4-{2-[(2R,3S)-3-[(2S,3S)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-yl]ethenyl}-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol
• IUPAC Traditional name: 5-[(2S,3S)-4-{2-[(2R,3S)-3-[(2S,3S)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-yl]ethenyl}-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol
• Synonyms: Vitisin C

Database IDs

• CAS Number: 180580-73-8
• PubChem SID: 162224449
• PubChem CID: 16145527
• CHEMBL: 442911
• Chemspider ID: 17301998
• Wikipedia Title: Vitisin_C

CALCULATED PROPERTIES

• Acid pKa: 8.577728
• H Acceptors: 12
• H Donor: 9
• LogD (pH = 5.5): 11.076341
• LogD (pH = 7.4): 11.048201
• Log P: 11.076701
• Molar Refractivity: 255.2075 cm^3
• Polarizability: 97.1369 Å^3
• Polar Surface Area: 209.76 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false