Fumagillin (CHEM002728)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (1)XML
Record Information
Version1.0
Creation Date2010-05-19 15:34:28 UTC
Update Date2026-03-31 20:50:39 UTC
Accession NumberCHEM002728
Identification
Common NameFumagillin
ClassSmall Molecule
DescriptionFumagillin is a mycotoxin found in the fungus Aspergillus fumigatus. It is an antimicrobial agent and amebicide that has been used in the treatment of microsporidiosis and other infections, especially in immunodeficient patients. It also has been investigated as a angiogenesis inhibitor in the treatment of cancer. Since fumagillin is often used to treat microsporidiosis in bees, it can be found as a contaminant in honey. (7, 1)
Contaminant Sources
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Ester
  • Ether
  • Fungal Toxin
  • Mycotoxin
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2E,4E,6E,8E)-10-({5-methoxy-4-[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-tetraenoateGenerator
Chemical FormulaC26H34O7
Average Molecular Mass458.551 g/mol
Monoisotopic Mass458.230 g/mol
CAS Registry Number23110-15-8
IUPAC Name(2E,4E,6E,8E)-10-({5-methoxy-4-[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
Traditional Namefumagillin
SMILES[H]\C(\C(\[H])=C(/[H])\C(\[H])=C(/[H])C(=O)OC1CCC2(CO2)C(C1OC)C1(C)OC1CC=C(C)C)=C(\[H])/C(/[H])=C(\[H])C(O)=O
InChI IdentifierInChI=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+
InChI KeyNGGMYCMLYOUNGM-HCNIIHBUSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-chain fatty acid
  • Branched fatty acid
  • Epoxy fatty acid
  • Fatty acid ester
  • Heterocyclic fatty acid
  • Dicarboxylic acid or derivatives
  • Unsaturated fatty acid
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Oxirane
  • Dialkyl ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical Roles
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0033 g/LALOGPS
logP4.61ALOGPS
logP4.05ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)4.88ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area97.89 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity128.37 m³·mol⁻¹ChemAxon
Polarizability51.06 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4l-0532900000-58570b780f981d2f84c1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-6934200000-8bd25782e4fbb98f8b82Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pw9-9520000000-813c35db19d9a8ca8b59Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0433900000-377cd105f8678bc71d25Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-07f3-1972400000-5bb94564613573ff7169Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ar3-5930000000-d0d92bc92d4734ccd33cSpectrum
Toxicity Profile
Route of ExposureOral, dermal, inhalation, and parenteral (contaminated drugs). (6)
Mechanism of ToxicityFumagillin blocks blood vessel formation (angiogenesis) by inhibiting the enzyme methionine aminopeptidase 2. This prevents angiogenesis by arresting endothelial cells in the G1 phase of the cell cycle. Inhibition of angiogenesis can suppress tumor growth and metastasis. Methionine aminopeptidase 2 inhibition also blocks Wnt signaling, which plays a critical role in development, cell differentiation, and tumorigenesis. (2, 3)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFumagillin is a mycotoxin found in the fungus Aspergillus fumigatus. It is an antimicrobial agent and amebicide that has been used in the treatment of microsporidiosis and other infections, especially in immunodeficient patients. It also has been investigated as a angiogenesis inhibitor in the treatment of cancer. Since fumagillin is often used to treat microsporidiosis in bees, it can be found as a contaminant in honey. (7, 1)
Minimum Risk LevelNot Available
Health EffectsFumagillin can be genotoxic, clastogenic, and cytotoxic. It may also cause thrombocytopenia, neutropenia and hyperlipasaemia. (1, 4, 5)
SymptomsFumagillin may cause abdominal cramps, vomiting, and diarrhea. (5)
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID5353634
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Peterson, M.H., Goldstein, A.W. and Denison, F.W. Jr.; U.S. Patent 2,803,586; August 20, 1957; assigned to Abbott Laboratories.

MSDSNot Available
General ReferencesNot Available