Diethyl fumarate

Details

• Internal ID: 3938578f-645c-4f6f-9ac6-f6430c800a1e
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acid esters
• IUPAC Name: diethyl (E)-but-2-enedioate
• SMILES (Canonical): CCOC(=O)C=CC(=O)OCC
• SMILES (Isomeric): CCOC(=O)/C=C/C(=O)OCC
• InChI: InChI=1S/C8H12O4/c1-3-11-7(9)5-6-8(10)12-4-2/h5-6H,3-4H2,1-2H3/b6-5+
• InChI Key: IEPRKVQEAMIZSS-AATRIKPKSA-N
• Popularity: 351 references in papers

Physical and Chemical Properties

• Molecular Formula: C₈H₁₂O₄
• Molecular Weight: 172.18 g/mol
• Exact Mass: 172.07355886 g/mol
• Topological Polar Surface Area (TPSA): 52.60 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 0.67
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

• 623-91-6
• Fumaric acid, diethyl ester
• Anti-Psoriaticum
• diethyl (2E)-but-2-enedioate
• Fumaric Acid Diethyl Ester
• 2-Butenedioic acid (E)-, diethyl ester
• diethyl (E)-but-2-enedioate
• 1,4-diethyl (2E)-but-2-enedioate
• 2-Butenedioic acid (2E)-, diethyl ester
• 2-Butenedioic acid, diethyl ester, (E)-
• NSC 20954
• Diethylester kyseliny fumarove
• trans-2-Butenedioic acid diethyl ester
• (E)-but-2-enedioic acid diethyl ester
• HSDB 5722
• EINECS 210-819-7
• UNII-5WBU5A3E8A
• Diethylester kyseliny fumarove [Czech]
• (2E)-2-Butenedioic acid diethyl ester
• BRN 0775347
• 5WBU5A3E8A
• AI3-05613
• DTXSID7027253
• CHEBI:87388
• NSC20954
• NSC-20954
• Diethylfumarate
• 2-Butenedioic acid (2E)-, 1,4-diethyl ester
• Diethyl 2-butenedioate
• WLN: 2OV1U1VO2
• 4-02-00-02207 (Beilstein Handbook Reference)
• Diethyl (2E)-2-butenedioate
• 1,4-diethyl but-2-enedioate
• Diethyl ester of (E)-2-Butenedioic acid
• Fumaric acid diethyl
• Diethyl fumarate, 98%
• Fumaric acid diethylester
• 2-Butenedioic acid(2e)-, 1,4-diethyl ester
• SCHEMBL42602
• SCHEMBL43033
• diethyl(2E)-but-2-enedioate
• DTXCID807253
• DIETHYL FUMARATE [HSDB]
• CHEMBL3187857
• AMY18090
• Tox21_200764
• BBL011468
• MFCD00064455
• STL146580
• AKOS000121052
• CS-W010772
• HY-W010056
• NCGC00248825-01
• NCGC00258318-01
• AS-14711
• CAS-623-91-6
• LS-46994
• 2-Butenedioic acid, (E)-, diethyl ester
• 2-butenedioic acid, diethyl ester, (2E)-
• Diethyl fumarate, purum, >=98.0% (GC)
• F0068
• diethyl (E)-but-2-enedioate;Diethyl fumarate
• EN300-16127
• EN300-313332
• A833754
• J-007453
• J-508564
• Q27159582
• F8886-8256
• 26298-06-6

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9774	97.74%
Caco-2	+	0.8471	84.71%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7920	79.20%
OATP2B1 inhibitior	-	0.8645	86.45%
OATP1B1 inhibitior	+	0.9612	96.12%
OATP1B3 inhibitior	+	0.9638	96.38%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8379	83.79%
P-glycoprotein inhibitior	-	0.9844	98.44%
P-glycoprotein substrate	-	0.9968	99.68%
CYP3A4 substrate	-	0.6641	66.41%
CYP2C9 substrate	-	0.6048	60.48%
CYP2D6 substrate	-	0.8904	89.04%
CYP3A4 inhibition	-	0.9360	93.60%
CYP2C9 inhibition	-	0.8862	88.62%
CYP2C19 inhibition	-	0.8922	89.22%
CYP2D6 inhibition	-	0.9432	94.32%
CYP1A2 inhibition	-	0.8765	87.65%
CYP2C8 inhibition	-	0.9648	96.48%
CYP inhibitory promiscuity	-	0.8116	81.16%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	+	0.5434	54.34%
Carcinogenicity (trinary)	Non-required	0.6938	69.38%
Eye corrosion	+	0.8476	84.76%
Eye irritation	+	0.9530	95.30%
Skin irritation	+	0.8705	87.05%
Skin corrosion	-	0.5090	50.90%
Ames mutagenesis	-	0.7800	78.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8206	82.06%
Micronuclear	-	0.9400	94.00%
Hepatotoxicity	-	0.5399	53.99%
skin sensitisation	+	0.9333	93.33%
Respiratory toxicity	-	0.9000	90.00%
Reproductive toxicity	-	0.6333	63.33%
Mitochondrial toxicity	-	0.9625	96.25%
Nephrotoxicity	+	0.6140	61.40%
Acute Oral Toxicity (c)	III	0.8515	85.15%
Estrogen receptor binding	-	0.8787	87.87%
Androgen receptor binding	-	0.8626	86.26%
Thyroid receptor binding	-	0.7764	77.64%
Glucocorticoid receptor binding	-	0.6557	65.57%
Aromatase binding	-	0.7366	73.66%
PPAR gamma	-	0.7354	73.54%
Honey bee toxicity	-	0.9392	93.92%
Biodegradation	+	0.8750	87.50%
Crustacea aquatic toxicity	-	0.8055	80.55%
Fish aquatic toxicity	+	0.9201	92.01%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.88%	96.09%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	89.69%	96.95%
CHEMBL4040	P28482	MAP kinase ERK2	85.12%	83.82%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	84.89%	97.21%
CHEMBL3401	O75469	Pregnane X receptor	83.91%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.57%	99.17%
CHEMBL221	P23219	Cyclooxygenase-1	82.00%	90.17%
CHEMBL2664	P23526	Adenosylhomocysteinase	81.71%	86.67%

Plants that contains it

• Vitis vinifera

Cross-Links

• PubChem: 638144
• NPASS: NPC281043