Mesaconic acid

Details

• Internal ID: d7ea059a-3365-4d99-be92-4006ca15a9e6
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acids and conjugates > Branched fatty acids > Methyl-branched fatty acids
• IUPAC Name: (E)-2-methylbut-2-enedioic acid
• SMILES (Canonical): CC(=CC(=O)O)C(=O)O
• SMILES (Isomeric): C/C(=C\C(=O)O)/C(=O)O
• InChI: InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2+
• InChI Key: HNEGQIOMVPPMNR-NSCUHMNNSA-N
• Popularity: 411 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): 74.60 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): 0.10
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• 498-24-8
• 2-Methylfumaric acid
• Methylfumaric acid
• mesaconate
• 2-Butenedioic acid, 2-methyl-, (2E)-
• Fumaric acid, methyl-
• trans-2-Methyl-2-butenedioic acid
• trans-1-Propene-1,2-dicarboxylic acid
• Kyselina mesakonova
• (2E)-2-METHYLBUT-2-ENEDIOIC ACID
• 2-methylfumarate
• 2-Butenedioic acid, 2-methyl-, (E)-
• Butenedioic acid, methyl-, (E)-
• 2-methylbut-2-enedioic acid
• Citronic acid
• (E)-2-methylbut-2-enedioic acid
• (E)-2-Methyl-2-butenedioic acid
• Kyselina mesakonova [Czech]
• NSC 65438
• (E)-Citraconic acid
• (2E)-2-Methyl-2-butenedioic acid
• EINECS 207-859-2
• BRN 1722680
• UNII-90UTM639KK
• 2-methyl-2E-butenedioic acid
• 90UTM639KK
• methylfumarate
• NSC32949
• NSC-65438
• 4-02-00-02231 (Beilstein Handbook Reference)
• Mesaconicacid
• 7407-59-2
• Citronic acid; Methylfumaric acid
• Citronate
• NSC-32949
• (E)-Citraconate
• Mesaconic acid, 99%
• bmse000746
• WLN: QVY1&U1VQ
• SCHEMBL5894
• MESACONIC ACID [MI]
• SCHEMBL28517
• trans-2-Methyl-2-butenedioate
• WLN: QVY1&U1VQ -T
• (2E)-2-Methyl-2-butenedioate
• CHEBI:16600
• DTXSID10883407
• MESACONIC ACID; MESACONATE
• NSC65438
• trans-1-Propene-1,2-dicarboxylate
• (E)-2-methyl-but-2-enedioic acid
• BBL023435
• LMFA01170116
• MFCD00002653
• STL299679
• AKOS000119631
• (2E)-2-Methyl-2-butenedioic acid #
• LS-89871
• CS-0368860
• M0066
• EN300-19991
• C01732
• 2-Butenedioic acid, 2-methyl-, (E)- (9CI)
• EN300-1387340
• Q3544981
• W-106002
• Z104476308
• FB1827E3-2A34-43A5-BDDC-481FC6606513

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9369	93.69%
Caco-2	+	0.6267	62.67%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7843	78.43%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9384	93.84%
OATP1B3 inhibitior	+	0.9540	95.40%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9787	97.87%
P-glycoprotein inhibitior	-	0.9859	98.59%
P-glycoprotein substrate	-	0.9907	99.07%
CYP3A4 substrate	-	0.7366	73.66%
CYP2C9 substrate	-	0.5764	57.64%
CYP2D6 substrate	-	0.9256	92.56%
CYP3A4 inhibition	-	0.9684	96.84%
CYP2C9 inhibition	-	0.8722	87.22%
CYP2C19 inhibition	-	0.9528	95.28%
CYP2D6 inhibition	-	0.9392	93.92%
CYP1A2 inhibition	-	0.9489	94.89%
CYP2C8 inhibition	-	0.9888	98.88%
CYP inhibitory promiscuity	-	0.9701	97.01%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	+	0.6256	62.56%
Carcinogenicity (trinary)	Non-required	0.6934	69.34%
Eye corrosion	+	0.7623	76.23%
Eye irritation	+	0.9826	98.26%
Skin irritation	+	0.7269	72.69%
Skin corrosion	+	0.9029	90.29%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8342	83.42%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	+	0.7573	75.73%
skin sensitisation	+	0.5872	58.72%
Respiratory toxicity	-	0.8667	86.67%
Reproductive toxicity	-	0.6111	61.11%
Mitochondrial toxicity	-	0.8625	86.25%
Nephrotoxicity	+	0.6132	61.32%
Acute Oral Toxicity (c)	III	0.7985	79.85%
Estrogen receptor binding	-	0.9615	96.15%
Androgen receptor binding	-	0.7597	75.97%
Thyroid receptor binding	-	0.9136	91.36%
Glucocorticoid receptor binding	-	0.8749	87.49%
Aromatase binding	-	0.9359	93.59%
PPAR gamma	-	0.8344	83.44%
Honey bee toxicity	-	0.9591	95.91%
Biodegradation	+	0.8250	82.50%
Crustacea aquatic toxicity	-	0.8500	85.00%
Fish aquatic toxicity	+	0.8992	89.92%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	86.56%	83.82%
CHEMBL2061	P19793	Retinoid X receptor alpha	82.38%	91.67%

Plants that contains it

• Saxifraga stolonifera

Cross-Links

• PubChem: 638129
• NPASS: NPC97348
• LOTUS: LTS0023859
• wikiData: Q3544981