(1S,3S,4S,5S,7R,8S)-7-ethyl-4-hydroxy-3-[(1E,3E,5E)-6-(4-methoxy-5-methyl-2-oxo-2H-pyran-6-yl)hexa-1,3,5-trien-1-yl]-1,5-dimethyl-2,6-dioxabicyclo[3.2.1]octan-8-yl acetate

• ChemBase ID: 5043
• Molecular Formular: C25H32O8
• Molecular Mass: 460.51678
• Monoisotopic Mass: 460.20971798
• SMILES: CC[C@@H]1[C@]2([C@H]([C@@]([C@H]([C@@H](O2)/C=C/C=C/C=C/c2c(c(cc(=O)o2)OC)C)O)(C)O1)OC(=O)C)C
• Canonical SMILES: CC[C@H]1O[C@@]2([C@@H]([C@@]1(C)O[C@H]([C@@H]2O)/C=C/C=C/C=C/c1oc(=O)cc(c1C)OC)OC(=O)C)C
• InChI: InChI=1S/C25H32O8/c1-7-20-24(4)23(30-16(3)26)25(5,33-20)22(28)18(32-24)13-11-9-8-10-12-17-15(2)19(29-6)14-21(27)31-17/h8-14,18,20,22-23,28H,7H2,1-6H3/b9-8+,12-10+,13-11+/t18-,20+,22-,23+,24-,25-/m0/s1
• InChIKey: QXCOFYWOWZJFEA-YJMRODJJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,3S,4S,5S,7R,8S)-7-ethyl-4-hydroxy-3-[(1E,3E,5E)-6-(4-methoxy-5-methyl-2-oxo-2H-pyran-6-yl)hexa-1,3,5-trien-1-yl]-1,5-dimethyl-2,6-dioxabicyclo[3.2.1]octan-8-yl acetate
• IUPAC Traditional name: (1S,3S,4S,5S,7R,8S)-7-ethyl-4-hydroxy-3-[(1E,3E,5E)-6-(4-methoxy-3-methyl-6-oxopyran-2-yl)hexa-1,3,5-trien-1-yl]-1,5-dimethyl-2,6-dioxabicyclo[3.2.1]octan-8-yl acetate
• Synonyms: AUROVERTIN B

Database IDs

• PubChem SID: 160968475; 99443865
• PubChem CID: 444853

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.912434
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 2.5531158
• LogD (pH = 7.4): 2.5531147
• Log P: 2.553116
• Molar Refractivity: 125.5026 cm^3
• Polarizability: 47.657284 Å^3
• Polar Surface Area: 100.52 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.02
• LOG S: -4.62
• Solubility (Water): 1.10e-02 g/l

DETAILS

DrugBank - DB07394

Drug information: experimental