3-[4-[(2R)-2-[[4-[(E)-but-1-enyl]-2,5-dioxofuran-3-yl]methyl]butyl]-2,5-dioxofuran-3-yl]propanoic acid

Details

• Internal ID: 9028ecf7-6205-4b6e-acae-10734129be70
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Pentacarboxylic acids and derivatives
• IUPAC Name: 3-[4-[(2R)-2-[[4-[(E)-but-1-enyl]-2,5-dioxofuran-3-yl]methyl]butyl]-2,5-dioxofuran-3-yl]propanoic acid
• SMILES (Canonical): CCC=CC1=C(C(=O)OC1=O)CC(CC)CC2=C(C(=O)OC2=O)CCC(=O)O
• SMILES (Isomeric): CC/C=C/C1=C(C(=O)OC1=O)C[C@H](CC)CC2=C(C(=O)OC2=O)CCC(=O)O
• InChI: InChI=1S/C20H22O8/c1-3-5-6-12-14(19(25)27-17(12)23)9-11(4-2)10-15-13(7-8-16(21)22)18(24)28-20(15)26/h5-6,11H,3-4,7-10H2,1-2H3,(H,21,22)/b6-5+/t11-/m0/s1
• InChI Key: LESRNXLJDKOYNX-QRGHLMKCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₂O₈
• Molecular Weight: 390.40 g/mol
• Exact Mass: 390.13146766 g/mol
• Topological Polar Surface Area (TPSA): 124.00 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.38
• H-Bond Acceptor: 7
• H-Bond Donor: 1
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9860	98.60%
Caco-2	-	0.6568	65.68%
Blood Brain Barrier	+	0.6605	66.05%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7807	78.07%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7858	78.58%
OATP1B3 inhibitior	+	0.9393	93.93%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7570	75.70%
BSEP inhibitior	+	0.6980	69.80%
P-glycoprotein inhibitior	-	0.6140	61.40%
P-glycoprotein substrate	-	0.8864	88.64%
CYP3A4 substrate	-	0.5328	53.28%
CYP2C9 substrate	+	0.6065	60.65%
CYP2D6 substrate	-	0.9012	90.12%
CYP3A4 inhibition	-	0.8536	85.36%
CYP2C9 inhibition	-	0.8972	89.72%
CYP2C19 inhibition	-	0.8611	86.11%
CYP2D6 inhibition	-	0.9261	92.61%
CYP1A2 inhibition	-	0.8494	84.94%
CYP2C8 inhibition	-	0.7617	76.17%
CYP inhibitory promiscuity	-	0.9642	96.42%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8625	86.25%
Carcinogenicity (trinary)	Non-required	0.6619	66.19%
Eye corrosion	-	0.9388	93.88%
Eye irritation	-	0.8046	80.46%
Skin irritation	-	0.5685	56.85%
Skin corrosion	-	0.9011	90.11%
Ames mutagenesis	-	0.7654	76.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.4308	43.08%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	+	0.5735	57.35%
skin sensitisation	-	0.8293	82.93%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	-	0.5444	54.44%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.5925	59.25%
Acute Oral Toxicity (c)	III	0.6275	62.75%
Estrogen receptor binding	+	0.7821	78.21%
Androgen receptor binding	-	0.4931	49.31%
Thyroid receptor binding	-	0.6409	64.09%
Glucocorticoid receptor binding	+	0.8054	80.54%
Aromatase binding	-	0.6229	62.29%
PPAR gamma	+	0.6955	69.55%
Honey bee toxicity	-	0.9495	94.95%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7400	74.00%
Fish aquatic toxicity	+	0.9735	97.35%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.73%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.85%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.97%	95.56%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	87.65%	95.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.20%	99.23%
CHEMBL230	P35354	Cyclooxygenase-2	86.12%	89.63%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.98%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	84.31%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.27%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.01%	91.11%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.02%	96.00%
CHEMBL221	P23219	Cyclooxygenase-1	81.34%	90.17%

Plants that contains it

• Picea rubens

Cross-Links

• PubChem: 162943772
• LOTUS: LTS0066953
• wikiData: Q105150774