methyl (1S,4aR,6S,7R,7aS)-4a,7-dihydroxy-6-{[(2E)-3-(4-methoxyphenyl)prop-2-enoyl]oxy}-7-methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylate

• ChemBase ID: 305741
• Molecular Formular: C27H34O14
• Molecular Mass: 582.55046
• Monoisotopic Mass: 582.19485577
• SMILES: [C@@]12([C@H]([C@@H](OC=C1C(=O)OC)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)[C@]([C@H](C2)OC(=O)/C=C/c1ccc(cc1)OC)(O)C)O
• Canonical SMILES: OC[C@H]1O[C@@H](O[C@@H]2OC=C([C@@]3([C@H]2[C@@](C)(O)[C@H](C3)OC(=O)/C=C/c2ccc(cc2)OC)O)C(=O)OC)[C@@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C27H34O14/c1-26(34)17(40-18(29)9-6-13-4-7-14(36-2)8-5-13)10-27(35)15(23(33)37-3)12-38-25(22(26)27)41-24-21(32)20(31)19(30)16(11-28)39-24/h4-9,12,16-17,19-22,24-25,28,30-32,34-35H,10-11H2,1-3H3/b9-6+/t16-,17+,19-,20+,21-,22-,24+,25+,26+,27+/m1/s1
• InChIKey: DVQVHBAATHWQAS-OALRNCSFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (1S,4aR,6S,7R,7aS)-4a,7-dihydroxy-6-{[(2E)-3-(4-methoxyphenyl)prop-2-enoyl]oxy}-7-methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylate
• IUPAC Traditional name: methyl (1S,4aR,6S,7R,7aS)-4a,7-dihydroxy-6-{[(2E)-3-(4-methoxyphenyl)prop-2-enoyl]oxy}-7-methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,5H,6H,7aH-cyclopenta[c]pyran-4-carboxylate
• Synonyms: Durantoside II

Database IDs

• CAS Number: 53526-66-2

CALCULATED PROPERTIES

• Acid pKa: 12.153335
• H Acceptors: 12
• H Donor: 6
• LogD (pH = 5.5): -1.112034
• LogD (pH = 7.4): -1.1120415
• Log P: -1.1120338
• Molar Refractivity: 136.0031 cm^3
• Polarizability: 54.73972 Å^3
• Polar Surface Area: 210.9 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: Powder