(2S,3R,4S,5S,6R)-2-{[(3S,4R,4aS)-4-ethenyl-8-oxo-3H,4H,4aH,5H,6H,8H-pyrano[3,4-c]pyran-3-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl 2,4-dihydroxy-6-(3-hydroxyphenyl)benzoate

• ChemBase ID: 125781
• Molecular Formular: C29H30O13
• Molecular Mass: 586.5407
• Monoisotopic Mass: 586.16864102
• SMILES: O=C1OCC[C@@H]2C1=CO[C@@H](O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1OC(=O)c1c(c3cccc(O)c3)cc(O)cc1O)CO)[C@@H]2C=C
• Canonical SMILES: OC[C@H]1O[C@@H](O[C@@H]2OC=C3[C@H]([C@H]2C=C)CCOC3=O)[C@@H]([C@H]([C@@H]1O)O)OC(=O)c1c(O)cc(cc1c1cccc(c1)O)O
• InChI: InChI=1S/C29H30O13/c1-2-16-17-6-7-38-26(36)19(17)12-39-28(16)42-29-25(24(35)23(34)21(11-30)40-29)41-27(37)22-18(9-15(32)10-20(22)33)13-4-3-5-14(31)8-13/h2-5,8-10,12,16-17,21,23-25,28-35H,1,6-7,11H2/t16-,17+,21-,23-,24+,25-,28+,29+/m1/s1
• InChIKey: DBOVHQOUSDWAPQ-WTONXPSSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4S,5S,6R)-2-{[(3S,4R,4aS)-4-ethenyl-8-oxo-3H,4H,4aH,5H,6H,8H-pyrano[3,4-c]pyran-3-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl 2,4-dihydroxy-6-(3-hydroxyphenyl)benzoate
• IUPAC Traditional name: amarogentin
• Synonyms: Amarogentin

Database IDs

• CAS Number: 21018-84-8
• PubChem SID: 162220128
• PubChem CID: 115149
• CHEBI ID: 2622
• CHEMBL: 451112
• Chemspider ID: 103033
• Wikipedia Title: Amarogentin

CALCULATED PROPERTIES

• Acid pKa: 8.439058
• H Acceptors: 11
• H Donor: 6
• LogD (pH = 5.5): 2.7521386
• LogD (pH = 7.4): 2.7147458
• Log P: 2.7526345
• Molar Refractivity: 142.3489 cm^3
• Polarizability: 57.332638 Å^3
• Polar Surface Area: 201.67 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false