Maleamic acid

Details

• Internal ID: d0fb42ad-f04a-4780-8587-10d23d163647
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acids and conjugates > Straight chain fatty acids
• IUPAC Name: (Z)-4-amino-4-oxobut-2-enoic acid
• SMILES (Canonical): C(=CC(=O)O)C(=O)N
• SMILES (Isomeric): C(=C\C(=O)O)\C(=O)N
• InChI: InChI=1S/C4H5NO3/c5-3(6)1-2-4(7)8/h1-2H,(H2,5,6)(H,7,8)/b2-1-
• InChI Key: FSQQTNAZHBEJLS-UPHRSURJSA-N
• Popularity: 198 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄H₅NO₃
• Molecular Weight: 115.09 g/mol
• Exact Mass: 115.026943022 g/mol
• Topological Polar Surface Area (TPSA): 80.40 Ų
• XlogP: -1.00
• Atomic LogP (AlogP): -0.89
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• 557-24-4
• Maleamate
• (Z)-4-amino-4-oxobut-2-enoic acid
• Maleic monoamide
• Maleic acid monoamide
• Acrylic acid, 3-carbamoyl-, (Z)-
• 2-butenoic acid, 4-amino-4-oxo-, (2Z)-
• (2Z)-3-carbamoylprop-2-enoic acid
• UNII-MJS1DTX3X1
• MJS1DTX3X1
• NSC 8155
• C4H5NO3
• EINECS 209-163-4
• (Z)-4-amino-4-oxo-2-butenoic acid
• (2Z)-4-amino-4-oxobut-2-enoic acid
• (2Z)-4-Amino-4-oxo-2-butenoic acid
• AI3-16135
• 4-amino-4-oxo-2-butenoic acid
• maleamidic acid
• NSC-8155
• cis-butenedioic imide
• bmse000460
• MALEAMIC ACID [MI]
• SCHEMBL14359
• (Z)-3-carbamoyl acrylic acid
• Maleamidic acid;Aminomaleic acid
• SCHEMBL23151874
• CHEBI:29045
• FSQQTNAZHBEJLS-UPHRSURJSA-
• NSC3246
• FSQQTNAZHBEJLS-UPHRSURJSA-N
• DTXSID301031738
• (E)-3-carbamoylprop-2-enoic acid
• NSC-3246
• (Z)-4-amino-4-oxobut-2-enoicacid
• MFCD00082354
• s3330
• AKOS002845346
• DS-9731
• (Z)-4-amino-4-keto-but-2-enoic acid
• 2-Butenoic acid, 4-amino-4-oxo-, (Z)-
• HY-128750
• CS-0102552
• M0003
• C01596
• (Z)-4-azanyl-4-oxidanylidene-but-2-enoic acid
• EN300-7275131
• A870113
• Q27104047
• Z3006267143
• 250B244D-950A-4448-A06D-416DD2187E2D
• InChI=1/C4H5NO3/c5-3(6)1-2-4(7)8/h1-2H,(H2,5,6)(H,7,8)/b2-1-
• 29996-04-1

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9635	96.35%
Caco-2	+	0.6668	66.68%
Blood Brain Barrier	+	0.9250	92.50%
Human oral bioavailability	+	0.6571	65.71%
Subcellular localzation	Mitochondria	0.6092	60.92%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9800	98.00%
OATP1B3 inhibitior	+	0.9572	95.72%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9834	98.34%
P-glycoprotein inhibitior	-	0.9871	98.71%
P-glycoprotein substrate	-	0.9888	98.88%
CYP3A4 substrate	-	0.7844	78.44%
CYP2C9 substrate	-	0.6092	60.92%
CYP2D6 substrate	-	0.8752	87.52%
CYP3A4 inhibition	-	0.9683	96.83%
CYP2C9 inhibition	-	0.9651	96.51%
CYP2C19 inhibition	-	0.9679	96.79%
CYP2D6 inhibition	-	0.9502	95.02%
CYP1A2 inhibition	-	0.9774	97.74%
CYP2C8 inhibition	-	0.9800	98.00%
CYP inhibitory promiscuity	-	0.9966	99.66%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.5007	50.07%
Carcinogenicity (trinary)	Non-required	0.4848	48.48%
Eye corrosion	-	0.9014	90.14%
Eye irritation	+	0.9901	99.01%
Skin irritation	-	0.6525	65.25%
Skin corrosion	-	0.9620	96.20%
Ames mutagenesis	-	0.9300	93.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.9077	90.77%
Micronuclear	+	0.6900	69.00%
Hepatotoxicity	+	0.6625	66.25%
skin sensitisation	-	0.9448	94.48%
Respiratory toxicity	-	0.6556	65.56%
Reproductive toxicity	-	0.5444	54.44%
Mitochondrial toxicity	-	0.6750	67.50%
Nephrotoxicity	-	0.6001	60.01%
Acute Oral Toxicity (c)	III	0.5940	59.40%
Estrogen receptor binding	-	0.9221	92.21%
Androgen receptor binding	-	0.8152	81.52%
Thyroid receptor binding	-	0.8943	89.43%
Glucocorticoid receptor binding	-	0.8617	86.17%
Aromatase binding	-	0.8889	88.89%
PPAR gamma	-	0.6946	69.46%
Honey bee toxicity	-	0.9326	93.26%
Biodegradation	+	0.6750	67.50%
Crustacea aquatic toxicity	-	0.9800	98.00%
Fish aquatic toxicity	-	0.6258	62.58%

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	85.63%	83.82%
CHEMBL221	P23219	Cyclooxygenase-1	80.66%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.31%	96.09%

Plants that contains it

• Pogostemon cablin

Cross-Links

• PubChem: 5280451
• NPASS: NPC24325
• LOTUS: LTS0235415
• wikiData: Q27104047