Identification

Name
Fumagillin
Accession Number
DB02640  (EXPT01509)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
International/Other Brands
Flisint (Sanofi) / Fugillin (Upjohn) / Furnidil (Abbott)
Categories
UNII
7OW73204U1
CAS number
23110-15-8
Weight
Average: 458.551
Monoisotopic: 458.230453435
Chemical Formula
C26H34O7
InChI Key
NGGMYCMLYOUNGM-CSDLUJIJSA-N
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
IUPAC 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]octan-6-yl]oxy}-10-oxodeca-2,4,6,8-tetraenoic acid
SMILES
CO[[email protected]@H]1[[email protected]@H](CC[[email protected]]2(CO2)[[email protected]]1[[email protected]@]1(C)O[[email protected]@H]1CC=C(C)C)OC(=O)\C=C\C=C\C=C\C=C\C(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UMethionine aminopeptidase 2
ligand
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Fumagillin.Approved
AcetyldigoxinAcetyldigoxin may decrease the cardiotoxic activities of Fumagillin.Experimental
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Fumagillin.Investigational
BevacizumabBevacizumab may increase the cardiotoxic activities of Fumagillin.Approved, Investigational
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Fumagillin.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Fumagillin.Approved, Investigational
CymarinCymarin may decrease the cardiotoxic activities of Fumagillin.Experimental
DeslanosideDeslanoside may decrease the cardiotoxic activities of Fumagillin.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Fumagillin.Approved, Investigational
DigoxinDigoxin may decrease the cardiotoxic activities of Fumagillin.Approved
Digoxin Immune Fab (Ovine)Digoxin Immune Fab (Ovine) may decrease the cardiotoxic activities of Fumagillin.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Fumagillin.Approved, Investigational
GitoformateGitoformate may decrease the cardiotoxic activities of Fumagillin.Experimental
Lanatoside CLanatoside C may decrease the cardiotoxic activities of Fumagillin.Experimental
MetildigoxinMetildigoxin may decrease the cardiotoxic activities of Fumagillin.Experimental
OleandrinOleandrin may decrease the cardiotoxic activities of Fumagillin.Experimental, Investigational
OuabainOuabain may decrease the cardiotoxic activities of Fumagillin.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Fumagillin.Approved, Vet Approved
PeruvosidePeruvoside may decrease the cardiotoxic activities of Fumagillin.Experimental
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Fumagillin.Approved
ProscillaridinProscillaridin may decrease the cardiotoxic activities of Fumagillin.Experimental
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Fumagillin.Approved, Investigational
Food Interactions
Not 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.

General References
Not Available
External Links
KEGG Compound
C09668
PubChem Compound
6917655
PubChem Substance
46505331
ChemSpider
5292885
BindingDB
50113436
ChEBI
48635
ChEMBL
CHEMBL32838
Therapeutic Targets Database
DNC000664
HET
FUG
Wikipedia
Fumagillin
ATC Codes
P01AX10 — Fumagillin

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)190-192Peterson, M.H., Goldstein, A.W. and Denison, F.W. Jr.; U.S. Patent 2,803,586; August 20, 1957; assigned to Abbott Laboratories.
Predicted Properties
PropertyValueSource
Water Solubility0.0033 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity128.37 m3·mol-1ChemAxon
Polarizability51.13 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.907
Blood Brain Barrier-0.5281
Caco-2 permeable-0.578
P-glycoprotein substrateSubstrate0.7621
P-glycoprotein inhibitor IInhibitor0.5957
P-glycoprotein inhibitor IIInhibitor0.8966
Renal organic cation transporterNon-inhibitor0.9216
CYP450 2C9 substrateNon-substrate0.8485
CYP450 2D6 substrateNon-substrate0.8869
CYP450 3A4 substrateSubstrate0.639
CYP450 1A2 substrateNon-inhibitor0.8839
CYP450 2C9 inhibitorNon-inhibitor0.7431
CYP450 2D6 inhibitorNon-inhibitor0.9299
CYP450 2C19 inhibitorNon-inhibitor0.7701
CYP450 3A4 inhibitorNon-inhibitor0.7188
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9386
Ames testAMES toxic0.6248
CarcinogenicityNon-carcinogens0.9203
BiodegradationNot ready biodegradable0.8205
Rat acute toxicity2.7268 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9914
hERG inhibition (predictor II)Non-inhibitor0.9147
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound 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.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Fatty Acyls
Sub Class
Fatty acids and conjugates
Direct Parent
Medium-chain fatty acids
Alternative Parents
Fatty acid esters / Epoxy fatty acids / Branched fatty acids / Unsaturated fatty acids / Dicarboxylic acids and derivatives / Enoate esters / Oxacyclic compounds / Epoxides / Dialkyl ethers / Carboxylic acids
show 3 more
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
show 13 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
dicarboxylic acid monoester, antibiotic antifungal drug, carboxylic ester, epoxide, organooxygen heterocyclic antibiotic, oxaspiro compound, meroterpenoid (CHEBI:48635) / Bisabolane sesquiterpenoids (LMPR0103060003)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Ligand
General Function
Poly(a) rna binding
Specific Function
Cotranslationally removes the N-terminal methionine from nascent proteins. The N-terminal methionine is often cleaved when the second residue in the primary sequence is small and uncharged (Met-Ala...
Gene Name
METAP2
Uniprot ID
P50579
Uniprot Name
Methionine aminopeptidase 2
Molecular Weight
52891.145 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:16