(1S,3S,4S,5R,6R,7R)-1-[(4S,5R)-4-(acetyloxy)-5-benzyl-3-methylidenehexyl]-6-{[(2E,4S,6S)-4,6-dimethyloct-2-enoyl]oxy}-4,7-dihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid

• ChemBase ID: 130235
• Molecular Formular: C35H46O14
• Molecular Mass: 690.73134
• Monoisotopic Mass: 690.28875615
• SMILES: CC[C@H](C)C[C@H](C)/C=C/C(=O)O[C@@H]1[C@H]([C@]2(O[C@@H]([C@]([C@@]1(O2)C(=O)O)(C(=O)O)O)C(=O)O)CCC(=C)[C@H]([C@H](C)Cc1ccccc1)OC(=O)C)O
• Canonical SMILES: CC[C@@H](C[C@@H](/C=C/C(=O)O[C@@H]1[C@@H](O)[C@@]2(O[C@@]1(C(=O)O)[C@](O)(C(=O)O)[C@H](O2)C(=O)O)CCC(=C)[C@H]([C@@H](Cc1ccccc1)C)OC(=O)C)C)C
• InChI: InChI=1S/C35H46O14/c1-7-19(2)17-20(3)13-14-25(37)47-28-27(38)33(48-29(30(39)40)34(45,31(41)42)35(28,49-33)32(43)44)16-15-21(4)26(46-23(6)36)22(5)18-24-11-9-8-10-12-24/h8-14,19-20,22,26-29,38,45H,4,7,15-18H2,1-3,5-6H3,(H,39,40)(H,41,42)(H,43,44)/b14-13+/t19-,20+,22+,26+,27+,28+,29+,33-,34+,35-/m0/s1
• InChIKey: DFKDOZMCHOGOBR-NCSQYGPNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,3S,4S,5R,6R,7R)-1-[(4S,5R)-4-(acetyloxy)-5-benzyl-3-methylidenehexyl]-6-{[(2E,4S,6S)-4,6-dimethyloct-2-enoyl]oxy}-4,7-dihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid
• IUPAC Traditional name: zaragozic acid
• Synonyms: squalestatin 1; Zaragozic acid

Database IDs

• CAS Number: 142561-96-4
• PubChem SID: 162224515
• PubChem CID: 6438355
• CHEMBL: 40991
• Wikipedia Title: Zaragozic_acid

CALCULATED PROPERTIES

• Acid pKa: 3.3979464
• H Acceptors: 12
• H Donor: 5
• LogD (pH = 5.5): 1.2316983
• LogD (pH = 7.4): -3.6660888
• Log P: 5.257308
• Molar Refractivity: 169.5212 cm^3
• Polarizability: 67.72101 Å^3
• Polar Surface Area: 223.42 Å^2
• Rotatable Bonds: 19
• Lipinski's Rule of Five: false