methyl (1S,4aS,5R,7S,7aS)-7-(acetyloxy)-5-hydroxy-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: 305173
• Molecular Formular: C19H28O12
• Molecular Mass: 448.41842
• Monoisotopic Mass: 448.15807634
• SMILES: [C@H]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[C@H]2O)(OC(=O)C)C
• Canonical SMILES: OC[C@H]1O[C@@H](O[C@@H]2OC=C([C@@H]3[C@H]2[C@@](C)(OC(=O)C)C[C@H]3O)C(=O)OC)[C@@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C19H28O12/c1-7(21)31-19(2)4-9(22)11-8(16(26)27-3)6-28-17(12(11)19)30-18-15(25)14(24)13(23)10(5-20)29-18/h6,9-15,17-18,20,22-25H,4-5H2,1-3H3/t9-,10-,11+,12-,13-,14+,15-,17+,18+,19+/m1/s1
• InChIKey: ARFRZOLTIRQFCI-NGQYDJQZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (1S,4aS,5R,7S,7aS)-7-(acetyloxy)-5-hydroxy-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,4aS,5R,7S,7aS)-7-(acetyloxy)-5-hydroxy-7-methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7aH-cyclopenta[c]pyran-4-carboxylate
• Synonyms: Barlerin; 8-O-Acetylshanzhiside methyl ester

Database IDs

• CAS Number: 57420-46-9

CALCULATED PROPERTIES

• Acid pKa: 12.205769
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -2.600896
• LogD (pH = 7.4): -2.6009026
• Log P: -2.600896
• Molar Refractivity: 97.9806 cm^3
• Polarizability: 40.42874 Å^3
• Polar Surface Area: 181.44 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Powder