4-Methylene-2-oxoglutarate

Details

• Internal ID: 78e1fbf3-ba07-48f4-b46e-037c81f2ab90
• Taxonomy: Organic acids and derivatives > Keto acids and derivatives > Gamma-keto acids and derivatives
• IUPAC Name: 2-methylidene-4-oxopentanedioic acid
• SMILES (Canonical): C=C(CC(=O)C(=O)O)C(=O)O
• SMILES (Isomeric): C=C(CC(=O)C(=O)O)C(=O)O
• InChI: InChI=1S/C6H6O5/c1-3(5(8)9)2-4(7)6(10)11/h1-2H2,(H,8,9)(H,10,11)
• InChI Key: OARCEFMISOKEKI-UHFFFAOYSA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆H₆O₅
• Molecular Weight: 158.11 g/mol
• Exact Mass: 158.02152329 g/mol
• Topological Polar Surface Area (TPSA): 91.70 Ų
• XlogP: -0.30
• Atomic LogP (AlogP): -0.33
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

• 2-Methylene-4-oxopentanedioic acid
• 2-Methylidene-4-oxopentanedioic acid
• 2-methylene-4-oxo-pentanedioic acid
• 4-Carboxy-2-oxo-4-pentenoate
• CHEBI:1898
• g-Methylene-a-ketoglutaric acid
• SCHEMBL1300526
• 2-Methylene-4-oxoglutaric acid
• LMFA01170047
• C06035
• Q27105522

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8639	86.39%
Caco-2	-	0.8093	80.93%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7702	77.02%
OATP2B1 inhibitior	-	0.8570	85.70%
OATP1B1 inhibitior	+	0.9630	96.30%
OATP1B3 inhibitior	+	0.9432	94.32%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9840	98.40%
P-glycoprotein inhibitior	-	0.9830	98.30%
P-glycoprotein substrate	-	0.9818	98.18%
CYP3A4 substrate	-	0.7538	75.38%
CYP2C9 substrate	+	0.5918	59.18%
CYP2D6 substrate	-	0.8647	86.47%
CYP3A4 inhibition	-	0.9189	91.89%
CYP2C9 inhibition	-	0.8898	88.98%
CYP2C19 inhibition	-	0.9389	93.89%
CYP2D6 inhibition	-	0.9452	94.52%
CYP1A2 inhibition	-	0.9444	94.44%
CYP2C8 inhibition	-	0.9906	99.06%
CYP inhibitory promiscuity	-	0.9611	96.11%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.6011	60.11%
Carcinogenicity (trinary)	Non-required	0.7096	70.96%
Eye corrosion	+	0.7921	79.21%
Eye irritation	+	0.9808	98.08%
Skin irritation	+	0.6442	64.42%
Skin corrosion	-	0.6818	68.18%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8355	83.55%
Micronuclear	-	0.6300	63.00%
Hepatotoxicity	+	0.6125	61.25%
skin sensitisation	+	0.7019	70.19%
Respiratory toxicity	-	0.7556	75.56%
Reproductive toxicity	-	0.9000	90.00%
Mitochondrial toxicity	-	0.7625	76.25%
Nephrotoxicity	+	0.7607	76.07%
Acute Oral Toxicity (c)	III	0.5153	51.53%
Estrogen receptor binding	-	0.9029	90.29%
Androgen receptor binding	-	0.8806	88.06%
Thyroid receptor binding	-	0.8600	86.00%
Glucocorticoid receptor binding	-	0.6406	64.06%
Aromatase binding	-	0.7875	78.75%
PPAR gamma	-	0.8154	81.54%
Honey bee toxicity	-	0.9461	94.61%
Biodegradation	+	0.7500	75.00%
Crustacea aquatic toxicity	-	0.8800	88.00%
Fish aquatic toxicity	+	0.8066	80.66%

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	97.44%	83.82%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.59%	99.17%

Plants that contains it

• Arachis hypogaea
• Lilium regale

Cross-Links

• PubChem: 440813
• LOTUS: LTS0038727
• wikiData: Q27105522