(2E,4E,6E,8E)-10-{[(1S,2S,4S)-4-hydroxy-2-methoxy-4-methyl-3-[(2R,3R)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]cyclohexyl]oxy}-10-oxodeca-2,4,6,8-tetraenoic acid

• ChemBase ID: 2366
• Molecular Formular: C26H36O7
• Molecular Mass: 460.55984
• Monoisotopic Mass: 460.24610349
• SMILES: CO[C@@H]1[C@H](CC[C@](C)(O)C1[C@@]1(C)O[C@@H]1CC=C(C)C)OC(=O)/C=C/C=C/C=C/C=C/C(=O)O
• Canonical SMILES: CO[C@@H]1[C@H](CC[C@](C1[C@@]1(C)O[C@@H]1CC=C(C)C)(C)O)OC(=O)/C=C/C=C/C=C/C=C/C(=O)O
• InChI: InChI=1S/C26H36O7/c1-18(2)14-15-20-26(4,33-20)24-23(31-5)19(16-17-25(24,3)30)32-22(29)13-11-9-7-6-8-10-12-21(27)28/h6-14,19-20,23-24,30H,15-17H2,1-5H3,(H,27,28)/b8-6+,9-7+,12-10+,13-11+/t19-,20+,23+,24?,25-,26-/m0/s1
• InChIKey: XXVWUXWNPOXVQB-GJNCDYHDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E,4E,6E,8E)-10-{[(1S,2S,4S)-4-hydroxy-2-methoxy-4-methyl-3-[(2R,3R)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]cyclohexyl]oxy}-10-oxodeca-2,4,6,8-tetraenoic acid
• IUPAC Traditional name: (2E,4E,6E,8E)-10-{[(1S,2S,4S)-4-hydroxy-2-methoxy-4-methyl-3-[(2R,3R)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]cyclohexyl]oxy}-10-oxodeca-2,4,6,8-tetraenoic acid
• Synonyms: Fumagillin

Database IDs

• CAS Number: 23110-15-8
• PubChem SID: 46505331; 160965817
• PubChem CID: 46936444

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.884221
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 3.2244115
• LogD (pH = 7.4): 1.4569262
• Log P: 3.9338615
• Molar Refractivity: 130.3412 cm^3
• Polarizability: 49.249138 Å^3
• Polar Surface Area: 105.59 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.45
• LOG S: -4.84
• Solubility (Water): 6.73e-03 g/l

DETAILS

DrugBank - DB02640

• Drug Groups: experimental
• External Links: Wikipedia