Monoethyl fumarate

Details

• Internal ID: 8308a8b6-cfa0-48cf-afb8-a0b296a945fd
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acid esters
• IUPAC Name: (E)-4-ethoxy-4-oxobut-2-enoic acid
• SMILES (Canonical): CCOC(=O)C=CC(=O)O
• SMILES (Isomeric): CCOC(=O)/C=C/C(=O)O
• InChI: InChI=1S/C6H8O4/c1-2-10-6(9)4-3-5(7)8/h3-4H,2H2,1H3,(H,7,8)/b4-3+
• InChI Key: XLYMOEINVGRTEX-ONEGZZNKSA-N
• Popularity: 154 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆H₈O₄
• Molecular Weight: 144.12 g/mol
• Exact Mass: 144.04225873 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): 0.19
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• 2459-05-4
• Ethyl fumarate
• Fumaric acid monoethyl ester
• (E)-4-ethoxy-4-oxobut-2-enoic acid
• mono-Ethyl fumarate
• Ethyl hydrogen fumarate
• 4-ethoxy-4-oxobut-2-enoic acid
• (E)-4-ethoxy-4-oxo-2-butenoic acid
• (2E)-4-ethoxy-4-oxobut-2-enoic acid
• Fumaric acid, monoethyl ester
• 2-Butenedioic acid (E)-, monoethyl ester
• Y3W849NG2N
• CHEMBL1771637
• 3249-53-4
• DTXSID1044485
• MFCD00002699
• NSC-524101
• 1-Ethyl fumarate
• Ethylhydrogenfumarat
• (2E)-4-Ethoxy-4-oxo-2-butenoic acid
• (~{Z})-4-ethoxy-4-oxidanylidene-but-2-enoic acid
• Fumaric acid, ethyl ester
• mono-Ethyl fumarate, 95%
• UNII-Y3W849NG2N
• SCHEMBL60569
• fumaric acid mono-ethyl ester
• SCHEMBL141140
• Monoethyl trans-2-butenedioate
• DTXCID9024485
• ETHYL FUMARATE [WHO-DD]
• 2-Butenedioic acid 1-ethyl ester
• DTXSID701021503
• EINECS 219-544-7
• Tox21_301978
• BDBM50342427
• NSC244252
• STK367237
• AKOS000118854
• HY-W019696
• NSC 524101
• NSC-244252
• NCGC00255854-01
• AS-12529
• CAS-3249-53-4
• (2E)-4-Ethoxy-4-oxo-2-butenoic acid #
• 2-Butenedioic acid (2E)-, 1-ethyl ester
• BB 0216624
• CS-0030808
• F0359
• EN300-19541
• EN300-364770
• A937009
• W-107299
• Q27294232
• Z2315575179
• mono-Ethyl fumarate, certified reference material, TraceCERT(R)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9727	97.27%
Caco-2	+	0.7110	71.10%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.8365	83.65%
OATP2B1 inhibitior	-	0.8641	86.41%
OATP1B1 inhibitior	+	0.9560	95.60%
OATP1B3 inhibitior	+	0.9630	96.30%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9592	95.92%
P-glycoprotein inhibitior	-	0.9906	99.06%
P-glycoprotein substrate	-	0.9936	99.36%
CYP3A4 substrate	-	0.6512	65.12%
CYP2C9 substrate	+	0.8047	80.47%
CYP2D6 substrate	-	0.9022	90.22%
CYP3A4 inhibition	-	0.9363	93.63%
CYP2C9 inhibition	-	0.8623	86.23%
CYP2C19 inhibition	-	0.9387	93.87%
CYP2D6 inhibition	-	0.9508	95.08%
CYP1A2 inhibition	-	0.9313	93.13%
CYP2C8 inhibition	-	0.9355	93.55%
CYP inhibitory promiscuity	-	0.9522	95.22%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	+	0.5008	50.08%
Carcinogenicity (trinary)	Non-required	0.6834	68.34%
Eye corrosion	-	0.6518	65.18%
Eye irritation	+	0.9750	97.50%
Skin irritation	+	0.8487	84.87%
Skin corrosion	+	0.7841	78.41%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8770	87.70%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.6649	66.49%
skin sensitisation	+	0.7828	78.28%
Respiratory toxicity	-	0.8889	88.89%
Reproductive toxicity	-	0.6222	62.22%
Mitochondrial toxicity	-	0.9500	95.00%
Nephrotoxicity	+	0.5276	52.76%
Acute Oral Toxicity (c)	III	0.8146	81.46%
Estrogen receptor binding	-	0.8683	86.83%
Androgen receptor binding	-	0.8322	83.22%
Thyroid receptor binding	-	0.8581	85.81%
Glucocorticoid receptor binding	-	0.7962	79.62%
Aromatase binding	-	0.8637	86.37%
PPAR gamma	-	0.7907	79.07%
Honey bee toxicity	-	0.9478	94.78%
Biodegradation	+	0.9000	90.00%
Crustacea aquatic toxicity	-	0.7955	79.55%
Fish aquatic toxicity	+	0.8828	88.28%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3785	Q8TDS4	Hydroxycarboxylic acid receptor 2	410 nM; 410 nM	Ki; Ki	PMID: 21167710; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	92.47%	83.82%
CHEMBL221	P23219	Cyclooxygenase-1	89.22%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.11%	96.09%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.45%	96.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.67%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.49%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	81.53%	94.73%
CHEMBL2664	P23526	Adenosylhomocysteinase	81.51%	86.67%

Plants that contains it

• Andrographis paniculata
• Carthamus arborescens

Cross-Links

• PubChem: 5358902
• NPASS: NPC41409
• ChEMBL: CHEMBL1771637