(2R,3S)-2-(3,4-dihydroxyphenyl)-6-[(2R,3S,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

• ChemBase ID: 129113
• Molecular Formular: C30H26O12
• Molecular Mass: 578.52024
• Monoisotopic Mass: 578.14242627
• SMILES: Oc1ccc(cc1O)[C@H]1Oc2cc(O)c([C@@H]3c4c(cc(O)cc4O)O[C@@H]([C@H]3O)c3ccc(O)c(O)c3)c(O)c2C[C@@H]1O
• Canonical SMILES: Oc1cc(O)c2c(c1)O[C@@H]([C@H]([C@@H]2c1c(O)cc2c(c1O)C[C@@H]([C@H](O2)c1ccc(c(c1)O)O)O)O)c1ccc(c(c1)O)O
• InChI: InChI=1S/C30H26O12/c31-13-7-19(36)24-23(8-13)42-30(12-2-4-16(33)18(35)6-12)28(40)26(24)25-20(37)10-22-14(27(25)39)9-21(38)29(41-22)11-1-3-15(32)17(34)5-11/h1-8,10,21,26,28-40H,9H2/t21-,26-,28-,29+,30+/m0/s1
• InChIKey: GMISZFQPFDAPGI-ZBRHZRBFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S)-2-(3,4-dihydroxyphenyl)-6-[(2R,3S,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
• IUPAC Traditional name: (2R,3S)-2-(3,4-dihydroxyphenyl)-6-[(2R,3S,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
• Synonyms: Procyanidin B6; Procyanidin B6

Database IDs

• PubChem SID: 162223412
• PubChem CID: 474540
• Chemspider ID: 416635
• Wikipedia Title: Procyanidin_B6

CALCULATED PROPERTIES

• Acid pKa: 8.696085
• H Acceptors: 12
• H Donor: 10
• LogD (pH = 5.5): 3.1154704
• LogD (pH = 7.4): 3.0940714
• Log P: 3.115745
• Molar Refractivity: 146.508 cm^3
• Polarizability: 56.12421 Å^3
• Polar Surface Area: 220.76 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false