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Fumagillin

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Category Human immunodeficiency Virus (HIV)
CAS 23110-15-8
Description 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 anti-infective and antiangiogenic agent.
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Product Information

Synonyms NSC-9168; Fumidil B; Fumagillin; Fumagilina; Fugillin; Fumidil
IUPAC Name (2E,4E,6E,8E)-10-[[(3R,4S,5S,6R)-5-methoxy-4-[(2R,3R)-2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-yl]oxy]-10-oxodeca-2,4,6,8-tetraenoic acid
Molecular Weight 458.54
Molecular Formula C26H34O7
Canonical SMILES CC(=CCC1C(O1)(C)C2C(C(CCC23CO3)OC(=O)C=CC=CC=CC=CC(=O)O)OC)C
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-CSDLUJIJSA-N
Boiling Point 484.03°C at 760 mmHg
Melting Point 189-194°C
Flash Point 198.8°C
Purity >98%
Density 1.1368 g/cm3
Solubility Soluble in ethanol, methanol, DMF or DMSO. Poor water solubility.
Appearance White to Off-white Solid
Storage -20°C
Complexity 879
Exact Mass 458.23045342
Index Of Refraction 1.562
In Vitro Fumagillin is an active amebicide and anti-infective isolated from the fungus Aspergillus fumigatus. Fumagillin does exhibit some side effects that have deterred its acceptance as a viable treatment, but the current body of research on the synthesis of novel analogs of this molecule shows an exciting and promising revival of this drug as both an anti-infective and antiangiogenic agent.
PSA 97.89000
Target Parasite; HIV; Antibiotic
Vapor Pressure 2.7E-16mmHg at 25°C
XLogP3-AA 4

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