(E)-3-(1H-benzo[d]imidazol-2-yl)-1-(6-chloro-2-hydroxy-4-phenylquinolin-3-yl)prop-2-en-1-one

Details

• Internal ID: 2bb48503-793c-49ef-b260-503cfabc9fbe
• Taxonomy: Organoheterocyclic compounds > Quinolines and derivatives > Phenylquinolines
• IUPAC Name: 3-[(E)-3-(1H-benzimidazol-2-yl)prop-2-enoyl]-6-chloro-4-phenyl-1H-quinolin-2-one
• SMILES (Canonical): C1=CC=C(C=C1)C2=C(C(=O)NC3=C2C=C(C=C3)Cl)C(=O)C=CC4=NC5=CC=CC=C5N4
• SMILES (Isomeric): C1=CC=C(C=C1)C2=C(C(=O)NC3=C2C=C(C=C3)Cl)C(=O)/C=C/C4=NC5=CC=CC=C5N4
• InChI: InChI=1S/C25H16ClN3O2/c26-16-10-11-18-17(14-16)23(15-6-2-1-3-7-15)24(25(31)29-18)21(30)12-13-22-27-19-8-4-5-9-20(19)28-22/h1-14H,(H,27,28)(H,29,31)/b13-12+
• InChI Key: SBOKKVUBLNZTCT-OUKQBFOZSA-N
• Popularity: 11 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₁₆ClN₃O₂
• Molecular Weight: 425.90 g/mol
• Exact Mass: 425.0931045 g/mol
• Topological Polar Surface Area (TPSA): 74.80 Ų
• XlogP: 4.70
• Atomic LogP (AlogP): 5.62
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

• 1233322-09-2
• (E)-3-(1H-benzo[d]imidazol-2-yl)-1-(6-chloro-2-hydroxy-4-phenylquinolin-3-yl)prop-2-en-1-one
• CHEMBL190313
• (E)-3-(3-(1H-benzo[d]imidazol-2-yl) acryloyl)-6-chloro-4-phenylquinolin-2(1H)-one
• BI 69A11
• 3-[(E)-3-(1H-benzimidazol-2-yl)prop-2-enoyl]-6-chloro-4-phenyl-1H-quinolin-2-one
• compound 5809365
• SCHEMBL2578486
• SCHEMBL2578489
• BDBM15187
• BDBM50540082
• AKOS001579464
• AKOS024574175
• AT27462
• NCGC00402356-02
• AS-16644
• PD129869
• BIM-0034205.P001
• F0016-1319
• F0266-2668
• Z276849884
• (E)-3-(3-(1H-benzo[d]imidazol-2-yl)acryloyl)-6-chloro-4-phenylquinolin-2(1H)-one
• 3-[(2E)-3-(1H-1,3-benzodiazol-2-yl)prop-2-enoyl]-6-chloro-4-phenyl-1,2-dihydroquinolin-2-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	-	0.6359	63.59%
Blood Brain Barrier	+	0.7287	72.87%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6949	69.49%
OATP2B1 inhibitior	-	0.8517	85.17%
OATP1B1 inhibitior	+	0.8781	87.81%
OATP1B3 inhibitior	+	0.9472	94.72%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.9769	97.69%
P-glycoprotein inhibitior	-	0.4691	46.91%
P-glycoprotein substrate	-	0.8425	84.25%
CYP3A4 substrate	+	0.6341	63.41%
CYP2C9 substrate	-	0.7855	78.55%
CYP2D6 substrate	-	0.8849	88.49%
CYP3A4 inhibition	-	0.6084	60.84%
CYP2C9 inhibition	-	0.6851	68.51%
CYP2C19 inhibition	-	0.6168	61.68%
CYP2D6 inhibition	-	0.8410	84.10%
CYP1A2 inhibition	+	0.8990	89.90%
CYP2C8 inhibition	+	0.8365	83.65%
CYP inhibitory promiscuity	-	0.5673	56.73%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7457	74.57%
Carcinogenicity (trinary)	Non-required	0.5745	57.45%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.8254	82.54%
Skin irritation	-	0.8740	87.40%
Skin corrosion	-	0.9551	95.51%
Ames mutagenesis	+	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4063	40.63%
Micronuclear	+	0.8800	88.00%
Hepatotoxicity	+	0.7176	71.76%
skin sensitisation	-	0.9142	91.42%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	+	0.7864	78.64%
Acute Oral Toxicity (c)	III	0.4557	45.57%
Estrogen receptor binding	+	0.8851	88.51%
Androgen receptor binding	+	0.8775	87.75%
Thyroid receptor binding	+	0.6661	66.61%
Glucocorticoid receptor binding	+	0.7977	79.77%
Aromatase binding	+	0.7292	72.92%
PPAR gamma	+	0.8936	89.36%
Honey bee toxicity	-	0.8895	88.95%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.5177	51.77%
Fish aquatic toxicity	+	0.8174	81.74%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	96.82%	91.71%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	95.72%	92.29%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	95.34%	86.92%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.29%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.82%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.69%	95.56%
CHEMBL1781	P11387	DNA topoisomerase I	89.35%	97.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	88.90%	95.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.74%	86.33%
CHEMBL2581	P07339	Cathepsin D	87.95%	98.95%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	87.62%	87.67%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	87.47%	94.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.01%	89.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	85.04%	93.03%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	84.48%	85.94%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	83.91%	94.23%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	83.71%	92.67%
CHEMBL1868	P17948	Vascular endothelial growth factor receptor 1	83.44%	96.47%
CHEMBL230	P35354	Cyclooxygenase-2	83.37%	89.63%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	81.75%	97.21%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.71%	99.23%
CHEMBL2083	P15090	Fatty acid binding protein adipocyte	81.58%	95.71%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.68%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	80.04%	94.73%

Plants that contains it

• Artemisia annua
• Elephantopus mollis
• Juglans mandshurica
• Pergularia tomentosa
• Tacca chantrieri

Cross-Links

• PubChem: 5343381
• LOTUS: LTS0134094
• wikiData: Q105249583