METHYL FUMARATE

General Information

Mainterm	METHYL FUMARATE
CAS Reg.No.(or other ID)	624-49-7
Regnum	175.105 175.300 176.170

From www.fda.gov

Computed Descriptors

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2D Structure
CID	637568
IUPAC Name	dimethyl (E)-but-2-enedioate
InChI	InChI=1S/C6H8O4/c1-9-5(7)3-4-6(8)10-2/h3-4H,1-2H3/b4-3+
InChI Key	LDCRTTXIJACKKU-ONEGZZNKSA-N
Canonical SMILES	COC(=O)C=CC(=O)OC
Molecular Formula	C6H8O4
Wikipedia	dimethyl fumarate

From Pubchem

Computed Properties

Property Name	Property Value
Molecular Weight	144.126
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	4
Complexity	141.0
CACTVS Substructure Key Fingerprint	A A A D c c B g O A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A G g A A A A A A C A C A g A I C C A A A B A C I A C D S C A A A A A A A A A A I C A A A A E A A B A A A I A A A E A A A A A A A I Y A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A = =
Topological Polar Surface Area	52.6
Monoisotopic Mass	144.042
Exact Mass	144.042
Compound Is Canonicalized	True
Formal Charge	0
Heavy Atom Count	10
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Isotope Atom Count	0
Covalently-Bonded Unit Count	1

From Pubchem

ADMET Predicted Profile --- Classification

Model	Result	Probability
Absorption
Blood-Brain Barrier	BBB+	0.9539
Human Intestinal Absorption	HIA+	0.9571
Caco-2 Permeability	Caco2+	0.5393
P-glycoprotein Substrate	Non-substrate	0.7847
P-glycoprotein Inhibitor	Non-inhibitor	0.9099
P-glycoprotein Inhibitor	Non-inhibitor	0.8912
Renal Organic Cation Transporter	Non-inhibitor	0.9458
Distribution
Subcellular localization	Mitochondria	0.7869
Metabolism
CYP450 2C9 Substrate	Non-substrate	0.8274
CYP450 2D6 Substrate	Non-substrate	0.9345
CYP450 3A4 Substrate	Non-substrate	0.6926
CYP450 1A2 Inhibitor	Non-inhibitor	0.9219
CYP450 2C9 Inhibitor	Non-inhibitor	0.9402
CYP450 2D6 Inhibitor	Non-inhibitor	0.9677
CYP450 2C19 Inhibitor	Non-inhibitor	0.9485
CYP450 3A4 Inhibitor	Non-inhibitor	0.9524
CYP Inhibitory Promiscuity	Low CYP Inhibitory Promiscuity	0.9363
Excretion
Toxicity
Human Ether-a-go-go-Related Gene Inhibition	Weak inhibitor	0.9800
Human Ether-a-go-go-Related Gene Inhibition	Non-inhibitor	0.9886
AMES Toxicity	Non AMES toxic	0.5361
Carcinogens	Carcinogens	0.5438
Fish Toxicity	High FHMT	0.8559
Tetrahymena Pyriformis Toxicity	Low TPT	0.7876
Honey Bee Toxicity	High HBT	0.8458
Biodegradation	Ready biodegradable	0.7926
Acute Oral Toxicity	III	0.7992
Carcinogenicity (Three-class)	Non-required	0.7460

From admetSAR

ADMET Predicted Profile --- Regression

Model	Value	Unit
Absorption
Aqueous solubility	-0.0955	LogS
Caco-2 Permeability	0.7848	LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity	1.8781	LD50, mol/kg
Fish Toxicity	0.6493	pLC50, mg/L
Tetrahymena Pyriformis Toxicity	-0.4560	pIGC50, ug/L

From admetSAR

Taxonomic Classification

Kingdom	Organic compounds
Superclass	Lipids and lipid-like molecules
Class	Fatty Acyls
Subclass	Fatty acid esters
Intermediate Tree Nodes	Not available
Direct Parent	Fatty acid esters
Alternative Parents	Methyl esters Hydrocarbon derivatives Organic oxides Enoate esters Dicarboxylic acids and derivatives Carbonyl compounds
Molecular Framework	Aliphatic acyclic compounds
Substituents	Fatty acid ester - Dicarboxylic acid or derivatives - Alpha,beta-unsaturated carboxylic ester - Enoate ester - Methyl ester - Carboxylic acid ester - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aliphatic acyclic compound
Description	This compound belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.

From ClassyFire

Targets

Target Details

Kelch-like ECH-associated protein 1

General Function:: Transcription factor binding
Specific Function:: Acts as a substrate adapter protein for the E3 ubiquitin ligase complex formed by CUL3 and RBX1 and targets NFE2L2/NRF2 for ubiquitination and degradation by the proteasome, thus resulting in the suppression of its transcriptional activity and the repression of antioxidant response element-mediated detoxifying enzyme gene expression. Retains NFE2L2/NRF2 and may also retain BPTF in the cytosol. Targets PGAM5 for ubiquitination and degradation by the proteasome.
Gene Name:: KEAP1
Uniprot ID:: Q14145
Molecular Weight:: 69665.765 Da

Target Details

Transcription factor p65

General Function:: Ubiquitin protein ligase binding
Specific Function:: NF-kappa-B is a pleiotropic transcription factor present in almost all cell types and is the endpoint of a series of signal transduction events that are initiated by a vast array of stimuli related to many biological processes such as inflammation, immunity, differentiation, cell growth, tumorigenesis and apoptosis. NF-kappa-B is a homo- or heterodimeric complex formed by the Rel-like domain-containing proteins RELA/p65, RELB, NFKB1/p105, NFKB1/p50, REL and NFKB2/p52 and the heterodimeric p65-p50 complex appears to be most abundant one. The dimers bind at kappa-B sites in the DNA of their target genes and the individual dimers have distinct preferences for different kappa-B sites that they can bind with distinguishable affinity and specificity. Different dimer combinations act as transcriptional activators or repressors, respectively. NF-kappa-B is controlled by various mechanisms of post-translational modification and subcellular compartmentalization as well as by interactions with other cofactors or corepressors. NF-kappa-B complexes are held in the cytoplasm in an inactive state complexed with members of the NF-kappa-B inhibitor (I-kappa-B) family. In a conventional activation pathway, I-kappa-B is phosphorylated by I-kappa-B kinases (IKKs) in response to different activators, subsequently degraded thus liberating the active NF-kappa-B complex which translocates to the nucleus. NF-kappa-B heterodimeric p65-p50 and p65-c-Rel complexes are transcriptional activators. The NF-kappa-B p65-p65 complex appears to be involved in invasin-mediated activation of IL-8 expression. The inhibitory effect of I-kappa-B upon NF-kappa-B the cytoplasm is exerted primarily through the interaction with p65. p65 shows a weak DNA-binding site which could contribute directly to DNA binding in the NF-kappa-B complex. Associates with chromatin at the NF-kappa-B promoter region via association with DDX1. Essential for cytokine gene expression in T-cells (PubMed:15790681).
Gene Name:: RELA
Uniprot ID:: Q04206
Molecular Weight:: 60218.53 Da

From T3DB