Monomethyl Fumarate

Details

• Internal ID: 06e197d8-c25d-4748-88c9-ee7a12c94dce
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acid esters
• IUPAC Name: (E)-4-methoxy-4-oxobut-2-enoic acid
• SMILES (Canonical): COC(=O)C=CC(=O)O
• SMILES (Isomeric): COC(=O)/C=C/C(=O)O
• InChI: InChI=1S/C5H6O4/c1-9-5(8)3-2-4(6)7/h2-3H,1H3,(H,6,7)/b3-2+
• InChI Key: NKHAVTQWNUWKEO-NSCUHMNNSA-N
• Popularity: 258 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅H₆O₄
• Molecular Weight: 130.10 g/mol
• Exact Mass: 130.02660867 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): -0.20
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 2756-87-8
• 4-methoxy-4-oxobut-2-enoic acid
• mono-Methyl fumarate
• Methyl hydrogen fumarate
• Fumaric acid monomethyl ester
• (E)-4-methoxy-4-oxobut-2-enoic acid
• Bafiertam
• (2E)-4-Methoxy-4-oxobut-2-enoic acid
• UNII-45IUB1PX8R
• 45IUB1PX8R
• monomethylis fumaras
• methylhydrogenfumarate
• fumarato de monometilo
• fumarate de monomethyle
• EINECS 220-412-6
• NSC-523835
• Monomethyl fumarate [USAN]
• CHEMBL589586
• CHEBI:167450
• DTXSID801016498
• NSC 523835
• (2Z)-2-ButenedioicAcid1-MethylEster-d3
• 2-Butenedioic acid (2E)-, 1-methyl ester
• Monomethyl fumarate (USAN)
• Maleicacidmonomethylester
• MFCD00063174
• monomethyl-fumarate
• (2E)-3-(methoxycarbonyl)prop-2-enoic acid
• mono-Methyl fumarate, 97%
• SCHEMBL60132
• SCHEMBL60133
• MONO-METHYLFUMARATE97
• Maleic acid mono(methyl ester)
• GTPL5786
• FumarsA currencyuremonomethylester
• DTXCID30209463
• MONOMETHYL FUMARATE [INN]
• BCP18454
• BDBM50342426
• MONOMETHYL FUMARATE [WHO-DD]
• s6889
• WHO 11163
• (E)-2-Butendioic acid, methyl ester
• (E)-4-methoxy-4-oxobut-2-enoicacid
• AKOS015892642
• 2(E)-Butenedioic acid 1-methyl ester
• DB14219
• MRF-0000756
• MONOMETHYL FUMARATE [ORANGE BOOK]
• AS-15353
• (E)-But-2-enedioic acid monomethyl ester
• FUMARIC ACID MONOMETHYL ESTER [MI]
• (2E)-4-Methoxy-4-oxo-2-butenoic acid #
• HY-103252
• CS-0026484
• M2413
• D11492
• EN300-1699172
• A876896
• J-017996
• J-522708
• Q27087639
• Fumaric acid monomethyl ester, Methyl hydrogen fumarate
• Z2315585555
• mono-Methyl fumarate, certified reference material, TraceCERT(R)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9444	94.44%
Caco-2	+	0.7150	71.50%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.8192	81.92%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9654	96.54%
OATP1B3 inhibitior	+	0.9673	96.73%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9752	97.52%
P-glycoprotein inhibitior	-	0.9878	98.78%
P-glycoprotein substrate	-	0.9863	98.63%
CYP3A4 substrate	-	0.6864	68.64%
CYP2C9 substrate	-	0.6000	60.00%
CYP2D6 substrate	-	0.8856	88.56%
CYP3A4 inhibition	-	0.9693	96.93%
CYP2C9 inhibition	-	0.9386	93.86%
CYP2C19 inhibition	-	0.9627	96.27%
CYP2D6 inhibition	-	0.9674	96.74%
CYP1A2 inhibition	-	0.9386	93.86%
CYP2C8 inhibition	-	0.9730	97.30%
CYP inhibitory promiscuity	-	0.9855	98.55%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	+	0.5846	58.46%
Carcinogenicity (trinary)	Non-required	0.7022	70.22%
Eye corrosion	+	0.6981	69.81%
Eye irritation	+	0.9912	99.12%
Skin irritation	+	0.6631	66.31%
Skin corrosion	+	0.8972	89.72%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7997	79.97%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	-	0.8125	81.25%
skin sensitisation	+	0.7183	71.83%
Respiratory toxicity	-	0.9222	92.22%
Reproductive toxicity	-	0.7000	70.00%
Mitochondrial toxicity	-	0.9000	90.00%
Nephrotoxicity	+	0.6372	63.72%
Acute Oral Toxicity (c)	III	0.5725	57.25%
Estrogen receptor binding	-	0.8721	87.21%
Androgen receptor binding	-	0.8231	82.31%
Thyroid receptor binding	-	0.9041	90.41%
Glucocorticoid receptor binding	-	0.8121	81.21%
Aromatase binding	-	0.9345	93.45%
PPAR gamma	-	0.8874	88.74%
Honey bee toxicity	-	0.9113	91.13%
Biodegradation	+	0.9500	95.00%
Crustacea aquatic toxicity	-	0.8000	80.00%
Fish aquatic toxicity	+	0.7430	74.30%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3785	Q8TDS4	Hydroxycarboxylic acid receptor 2	180 nM	Ki	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	95.59%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.53%	96.09%
CHEMBL340	P08684	Cytochrome P450 3A4	81.18%	91.19%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.13%	99.17%

Plants that contains it

• Fumaria indica
• Maclura cochinchinensis
• Rothmannia longiflora
• Tagetes minuta

Cross-Links

• PubChem: 5369209
• LOTUS: LTS0036828
• wikiData: Q27087639