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Fumagillin

Fumagillin structure

CAS No:
23110-15-8
Formula:
C26H34O7
Chemical Name:
Fumagillin
Synonyms:
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,(2E,4E,6E,8E)-;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;2,4,6,8-Decatetraenedioic acid,mono[5-methoxy-4-[2-methyl-3-(3-methyl-2-butenyl)oxiranyl]-1-oxaspiro[2.5]oct-6-yl] ester,[3R-[3α,4α(2R*,3R*),5β,6β(2E,4E,6E,8E)]]-;2,4,6,8-Decatetraenedioic acid 4-(1,2-epoxy-1,5-dimethyl-4-hexenyl)-5-methoxy-1-oxaspiro[2.5]oct-6-yl ester;2,4,6,8-Decatetraenedioic acid,mono[(3R,4S,5S,6R)-5-methoxy-4-[(2R,3R)-2-methyl-3-(3-methyl-2-butenyl)oxiranyl]-1-oxaspiro[2.5]oct-6-yl] ester,(2E,4E,6E,8E)-;1-Oxaspiro[2.5]octane,2,4,6,8-decatetraenedioic acid deriv.;Fumidil;Fumagillin;Fumagillin DCH;Amebacilin;Fugillin;Fumadil B;(-)-Fumagillin;NSC 9168;ZGN 201;106215-84-3;297-95-0;47721-00-6;47721-01-7;746540-00-1
Categories:
Active Pharmaceutical Ingredients > Antibiotics

Description

Fumagillin(NSC9168) is a complex biomolecule and used as an antimicrobial agent.Target: AntiparasiticFumagillin 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 [1]

Fumagillin Basic Attributes

Molecular Weight：

458.54

Exact Mass：

458.54

EC Number：

245-433-8

DSSTox ID：

DTXSID7040736

HScode：

29419090

Characteristics

PSA：

97.9 Å²

Appearance：

white powder

Density：

1.172 g/cm³

Melting Point：

194.5 °C

Flash Point：

2℃

Refractive Index：

1.562

Water Solubility：

ethanol: 1 mg/mL

Storage Conditions：

−20°C

Toxicity：

LD50 in mice (mg/kg): ~800 s.c. (DiPaolo)

Specific rotation：

D25 -26.6° (c = 1 in 95% ethanol)

Safety Information

Packing level：

Ⅱ

Transport codes：

UN 1648 3 / PGII

wgk germany：

hazard class code：

22-36-20/21/22-11

safety instructions：

36-36/37-16-24/25

RTECS Number：

HE1750000

Marks：

Xn,F

Precautionary statement(s)：

P210-P280-P305 + P351 + P338

Hazard Statements：

H225-H302-H312-H319-H332

GHS Classification：

|Warning|H302 (95.35%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 43 companies from 5 notifications to the ECHA C&L Inventory.

Fumagillin Use and Manufacturing

Fumagillin is a polyene mycotoxin isolated from Aspergillus fumigatus in 1951 as a potent antiprotozoan for the treatment of amoebiasis. More recently, fumagillin has been shown to inhibit endothelial cell proliferation and angiogenesis by inhibiting methionine aminopeptidase-2 (MetAP-2).

Computed Properties

Molecular Weight:458.5
XLogP3:4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:11
Exact Mass:458.23045342
Monoisotopic Mass:458.23045342
Topological Polar Surface Area:97.9
Heavy Atom Count:33
Complexity:879
Undefined Atom Stereocenter Count:6
Undefined Bond Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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