LIPID MAPS

Structure Database (LMSD)

Common Name

fumagillin

Systematic Name

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

Synonyms

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
Fumagillin

LM ID

LMPR0103060003

Formula

C₂₆H₃₄O₇

Exact Mass

Calculate m/z

458.230455

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View MassBank spectra

Classification

Biological Context

Fumagillin is a fungal metabolite that has been found in A. fumigatus and has diverse biological activities.^1,2,3,4,5 It inhibits methionyl aminopeptidase 2 (METAP2; IC50 = 10 nM).¹ Fumagillin (10 ng/ml) inhibits tube formation in a rat blood vessel organ culture assay.² It inhibits E. cuniculi replication in isolated rabbit kidney cells and canine embryo cells when used at a concentration of 5 µg/ml.³ In vivo, fumagillin (30 mg/kg per day) decreases tumor growth and the number of metastases in a mouse model of diethylnitrosamine-induced hepatocellular carcinoma.⁴ It also reduces subcutaneous and gonadal fat mass in a mouse model of high-fat diet-induced obesity.⁵ Formulations containing fumagillin have been used to treat conjunctival and intestinal microsporidial infections in immunocompromised patients.

This information has been provided by Cayman Chemical

References

1. Griffith, E.C., Su, Z., Niwayama, S., et al. Molecular recognition of angiogenesis inhibitors fumagillin and ovalicin by methionine aminopeptidase 2. Proc. Natl. Acad. Sci. USA 95(26), 15183-15188 (1998).

2. Lijnen, H.R., Frederix, L., and Van Hoef, B. Fumagillin reduces adipose tissue formation in murine models of nutritionally induced obesity. Obesity 18(2), 2241-2246 (2010).

3. Sheen, I.S., Jeng, K.S., Jeng, W.J., et al. Fumagillin treatment of hepatocellular carcinoma in rats: An in vivo study of antiangiogenesis. World J. Gastroenterol. 11(6), 771-777 (2005).

4. Shadduck, J.A. Effect of fumagillin on in vitro multiplication of Encephalitozoon cuniculi. J. Protozool. 27(2), 202-208 (1980).

5. Kusaka, M., Sudo, K., Fujita, T., et al. Potent anti-angiogenic action of AGM-1470: Comparison to the fumagillin parent. Biochem. Biophys. Res. Commun. 174(3), 1070-1076 (1991).

String Representations

InChiKey (Click to copy)

NGGMYCMLYOUNGM-CSDLUJIJSA-N

InChi (Click to copy)

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

SMILES (Click to copy)

[C@]1([C@]2(OC2)CC[C@@H](OC(=O)/C=C/C=C/C=C/C=C/C(O)=O)[C@H]1OC)([H])[C@]1(C)[C@@H](C/C=C(/C)\C)O1