(2E,4E,6E,8E)-10-{[(3R,4S,5R,6R)-5-methoxy-4-[(2R,3R)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-yl]oxy}-10-oxodeca-2,4,6,8-tetraenoic acid

• ChemBase ID: 169497
• Molecular Formular: C26H34O7
• Molecular Mass: 458.54396
• Monoisotopic Mass: 458.23045343
• SMILES: C(=C\C=C\C=C\C=C\C(=O)O[C@@H]1CC[C@@]2([C@H]([C@H]1OC)[C@@]1([C@H](O1)CC=C(C)C)C)CO2)/C(=O)O
• Canonical SMILES: CO[C@H]1[C@@H](CC[C@@]2([C@H]1[C@@]1(C)O[C@@H]1CC=C(C)C)CO2)OC(=O)/C=C/C=C/C=C/C=C/C(=O)O
• InChI: InChI=1S/C26H34O7/c1-18(2)13-14-20-25(3,33-20)24-23(30-4)19(15-16-26(24)17-31-26)32-22(29)12-10-8-6-5-7-9-11-21(27)28/h5-13,19-20,23-24H,14-17H2,1-4H3,(H,27,28)/b7-5+,8-6+,11-9+,12-10+/t19-,20-,23+,24-,25+,26+/m1/s1
• InChIKey: NGGMYCMLYOUNGM-HVXGILEMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E,4E,6E,8E)-10-{[(3R,4S,5R,6R)-5-methoxy-4-[(2R,3R)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-yl]oxy}-10-oxodeca-2,4,6,8-tetraenoic acid
• IUPAC Traditional name: (2E,4E,6E,8E)-10-{[(3R,4S,5R,6R)-5-methoxy-4-[(2R,3R)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-yl]oxy}-10-oxodeca-2,4,6,8-tetraenoic acid
• Synonyms: Amebacilin; Fugillin; Fumadil B; Fumagillin DCH; Fumidil; NSC 9168; Fumagillin; (2E,4E,6E,8E)-2,4,6,8-Decatetraenedioic Acid 1-[(3R,4S,5S,6R)-5-Methoxy-4-[(2R,3R)-2-methyl-3-(3-methyl-2-buten-1-yl)-2-oxiranyl]-1-oxaspiro[2.5]oct-6-yl] Ester; 2,4,6,8-Decatetraenedioic Acid mono[4-(1,2-epoxy-1,5-dimethyl-4-hexenyl)-5-methoxy-1-oxaspiro[2.5]oct-6-yl] Ester; (-)-Fumagillin

Database IDs

• CAS Number: 23110-15-8
• PubChem SID: 162263629
• PubChem CID: 71317005

CALCULATED PROPERTIES

• Acid pKa: 4.884221
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 3.339205
• LogD (pH = 7.4): 1.5717199
• Log P: 4.048655
• Molar Refractivity: 128.3748 cm^3
• Polarizability: 48.59852 Å^3
• Polar Surface Area: 97.89 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - F862650

Fumagillin is a compound isolated from the fungus Aspergillus fumigatus. Fumagillin is an antimicrobial agent used in the treatment of microsporidiosis. Fumagillin shows promise as both an an anti-infective and antiangiogenic agent.

REFERENCES

• Molina, J.M. et al.: N. Eng. J. Med., 346, 1963 (2002)
• Hou, L. et al.: Pathol. Int., 59, 448 (2002)
• Ingber, D. et al.: Nature, 348, 555 (2002)