Coumarin 7

Details

• Internal ID: 25762400-eabd-460e-b1d6-8063226121d3
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives
• IUPAC Name: 3-(1H-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one
• SMILES (Canonical): CCN(CC)C1=CC2=C(C=C1)C=C(C(=O)O2)C3=NC4=CC=CC=C4N3
• SMILES (Isomeric): CCN(CC)C1=CC2=C(C=C1)C=C(C(=O)O2)C3=NC4=CC=CC=C4N3
• InChI: InChI=1S/C20H19N3O2/c1-3-23(4-2)14-10-9-13-11-15(20(24)25-18(13)12-14)19-21-16-7-5-6-8-17(16)22-19/h5-12H,3-4H2,1-2H3,(H,21,22)
• InChI Key: GOLORTLGFDVFDW-UHFFFAOYSA-N
• Popularity: 45 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₉N₃O₂
• Molecular Weight: 333.40 g/mol
• Exact Mass: 333.147726857 g/mol
• Topological Polar Surface Area (TPSA): 58.20 Ų
• XlogP: 4.00
• Atomic LogP (AlogP): 4.18
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

• 27425-55-4
• 3-(2-Benzimidazolyl)-7-(diethylamino)coumarin
• DISPERSE YELLOW 82
• 12239-58-6
• 2H-1-Benzopyran-2-one, 3-(1H-benzimidazol-2-yl)-7-(diethylamino)-
• Coumarin, 3-(2-benzimidazolyl)-7-(diethylamino)-
• 3-(1H-benzo[d]imidazol-2-yl)-7-(diethylamino)-2H-chromen-2-one
• 3-(1H-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one
• 3-(1H-Benzimidazol-2-yl)-7-(diethylamino)-2-benzopyrone
• 3-(1H-Benzimidazol-2-yl)-7-(diethylamino)-2H-chromen-2-one
• C.I. Disperse Yellow 82
• MLS000106044
• 3-(1H-1,3-benzodiazol-2-yl)-7-(diethylamino)chromen-2-one
• 3-(Benzimidazol-2-yl)-7-diethylaminocoumarin
• EINECS 248-451-4
• NSC303254
• NSC 303254
• NSC-303254
• SMR000103015
• KSC-16-133
• COUMARIN7
• Coumarin,
• coumarin-7
• Yellow 8GFF
• MFCD00051348
• Disperse Yellow 8GFF
• Coumarin 7, 98%
• D820 Savannah Yellow
• Fluorescent Yellow 10G
• Enamine_000185
• Oprea1_440779
• CBDivE_006555
• cid_94381
• BIDD:GT0472
• SCHEMBL180716
• REGID_for_CID_94381
• CHEMBL374632
• VX3Q255SG5
• Terasil Brilliant Flavine 8GFF
• DTXSID4067309
• BDBM37601
• 3-(1H-Benzoimidazol-2-yl)-7-diethylamino-chromen-2-one
• HMS1394I09
• HMS2467L12
• KUC105942N
• Sumikaron Brilliant Flavine S 10G
• AMY10383
• 3-(1H-1,3-benzodiazol-2-yl)-7-(diethylamino)-2H-chromen-2-one
• CID 94381
• KUC105942
• STK325581
• AKOS000415301
• AS-71890
• HY-125750
• B2111
• CS-0094880
• FT-0624079
• T70702
• 3-(2'-Benzimidazolyl)-7-(diethylamino)coumarin
• 3-(Benzimidazol-2-yl)-7-(diethylamino)coumarin
• SR-01000389310
• 3-(1H-benzimidazol-2-yl)-7-(diethylamino)coumarin
• SR-01000389310-1
• W-110701
• BRD-K85676811-001-08-2
• Z56758388
• F0266-2430
• 3-(Benzimidazol-2-yl)-7-diethylamino-2H-benzopyran-2-one
• 3-(1H-benzimidazol-2-yl)-7-(diethylamino)-1-benzopyran-2-one
• 3-(1H-Benzimidazol-2-yl)-7-(diethylamino)-2H-1-benzopyran-2-one
• 3-(1H-Benzimidazol-2-yl)-7-(diethylamino)-2H-chromen-2-one #
• 2H-1-benzopirano-2-ona, 3-(1H-benzimidazol-2-il)-7-(dietilamino)-
• 2-Oxylato-3-(3-azonia-1-aza-1H-indene-2-yl)-7-(diethyliminio)-7H-1-benzopyran

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9954	99.54%
Caco-2	+	0.5797	57.97%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Lysosomes	0.5726	57.26%
OATP2B1 inhibitior	-	0.7145	71.45%
OATP1B1 inhibitior	+	0.9133	91.33%
OATP1B3 inhibitior	+	0.9398	93.98%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9412	94.12%
P-glycoprotein inhibitior	+	0.6903	69.03%
P-glycoprotein substrate	-	0.5851	58.51%
CYP3A4 substrate	+	0.5297	52.97%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8316	83.16%
CYP3A4 inhibition	-	0.6006	60.06%
CYP2C9 inhibition	-	0.6802	68.02%
CYP2C19 inhibition	+	0.6285	62.85%
CYP2D6 inhibition	-	0.6521	65.21%
CYP1A2 inhibition	+	0.8030	80.30%
CYP2C8 inhibition	+	0.6771	67.71%
CYP inhibitory promiscuity	+	0.7727	77.27%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.4482	44.82%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.6937	69.37%
Skin irritation	-	0.7876	78.76%
Skin corrosion	-	0.9508	95.08%
Ames mutagenesis	-	0.5724	57.24%
Human Ether-a-go-go-Related Gene inhibition	+	0.8729	87.29%
Micronuclear	+	0.8900	89.00%
Hepatotoxicity	+	0.6000	60.00%
skin sensitisation	-	0.8646	86.46%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.6335	63.35%
Acute Oral Toxicity (c)	III	0.5116	51.16%
Estrogen receptor binding	+	0.8702	87.02%
Androgen receptor binding	+	0.7458	74.58%
Thyroid receptor binding	+	0.7348	73.48%
Glucocorticoid receptor binding	+	0.8422	84.22%
Aromatase binding	+	0.8603	86.03%
PPAR gamma	+	0.9090	90.90%
Honey bee toxicity	-	0.9018	90.18%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.8317	83.17%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5990	P38398	Breast cancer type 1 susceptibility protein	125.9 nM; 125.9 nM	Potency; Potency	via Super-PRED; via CMAUP
CHEMBL4801	P29466	Caspase-1	158.5 nM; 158.5 nM	Potency; Potency	via CMAUP; via Super-PRED
CHEMBL3468	P55210	Caspase-7	158.5 nM; 158.5 nM	Potency; Potency	via CMAUP; via Super-PRED
CHEMBL4096	P04637	Cellular tumor antigen p53	316.2 nM; 398.1 nM; 316.2 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via Super-PRED
CHEMBL4331	P68871	Hemoglobin beta chain	794.3 nM; 794.3 nM	Potency; Potency	via Super-PRED; via CMAUP
CHEMBL1293299	Q03164	Histone-lysine N-methyltransferase MLL	446.7 nM; 446.7 nM	Potency; Potency	via CMAUP; via Super-PRED
CHEMBL5514	P42858	Huntingtin	316.2 nM; 316.2 nM	Potency; Potency	via Super-PRED; via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	1584.9 nM	Potency	via CMAUP
CHEMBL5162	Q6W5P4	Neuropeptide S receptor	12589.3 nM	Potency	via CMAUP
CHEMBL1293277	O15118	Niemann-Pick C1 protein	281.8 nM; 281.8 nM	Potency; Potency	via Super-PRED; via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	1122 nM	Potency	via CMAUP
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	2324 nM	IC50	via CMAUP
CHEMBL1293294	P51151	Ras-related protein Rab-9A	100 nM; 100 nM	Potency; Potency	via Super-PRED; via CMAUP
CHEMBL3797	Q13315	Serine-protein kinase ATM	8912.5 nM	Potency	via CMAUP
CHEMBL1293227	O75604	Ubiquitin carboxyl-terminal hydrolase 2	199.5 nM; 199.5 nM; 891.3 nM	Potency; Potency; Potency	via Super-PRED; via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.19%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	96.63%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.49%	86.33%
CHEMBL3192	Q9BY41	Histone deacetylase 8	91.34%	93.99%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.28%	94.00%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	91.11%	96.67%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	90.57%	85.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.33%	89.00%
CHEMBL1913	P09619	Platelet-derived growth factor receptor beta	89.29%	95.70%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.03%	99.23%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	87.93%	93.65%
CHEMBL1937	Q92769	Histone deacetylase 2	87.24%	94.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.28%	95.56%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	85.78%	85.49%
CHEMBL3524	P56524	Histone deacetylase 4	84.62%	92.97%
CHEMBL255	P29275	Adenosine A2b receptor	83.82%	98.59%
CHEMBL1287628	Q9Y5S8	NADPH oxidase 1	83.52%	95.48%
CHEMBL1868	P17948	Vascular endothelial growth factor receptor 1	83.46%	96.47%
CHEMBL1781	P11387	DNA topoisomerase I	82.14%	97.00%
CHEMBL1628481	P35414	Apelin receptor	81.81%	97.89%
CHEMBL2535	P11166	Glucose transporter	81.20%	98.75%
CHEMBL4302	P08183	P-glycoprotein 1	80.49%	92.98%

Plants that contains it

• Angelica dahurica
• Angelica decursiva
• Artemisia capillaris
• Cinnamomum aromaticum
• Cnidium monnieri
• Glycyrrhiza glabra
• Glycyrrhiza inflata
• Glycyrrhiza uralensis
• Hansenia forbesii
• Hansenia weberbaueriana
• Kitagawia praeruptora
• Torilis japonica

Cross-Links

• PubChem: 94381
• NPASS: NPC187145
• ChEMBL: CHEMBL374632