3-Benzoyl-7-methoxycoumarin

Details

• Internal ID: d51e804f-6bdd-40f1-ae7c-decb5c13a815
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbonyl compounds > Phenylketones > Aryl-phenylketones
• IUPAC Name: 3-benzoyl-7-methoxychromen-2-one
• SMILES (Canonical): COC1=CC2=C(C=C1)C=C(C(=O)O2)C(=O)C3=CC=CC=C3
• SMILES (Isomeric): COC1=CC2=C(C=C1)C=C(C(=O)O2)C(=O)C3=CC=CC=C3
• InChI: InChI=1S/C17H12O4/c1-20-13-8-7-12-9-14(17(19)21-15(12)10-13)16(18)11-5-3-2-4-6-11/h2-10H,1H3
• InChI Key: HYORIVUCOQKMOC-UHFFFAOYSA-N
• Popularity: 9 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₂O₄
• Molecular Weight: 280.27 g/mol
• Exact Mass: 280.07355886 g/mol
• Topological Polar Surface Area (TPSA): 52.60 Ų
• XlogP: 3.40
• Atomic LogP (AlogP): 3.03
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

• 64267-12-5
• 3-benzoyl-7-methoxy-2H-chromen-2-one
• 3-Benzoyl-7-methoxy coumarin
• 3-benzoyl-7-methoxychromen-2-one
• 7-methoxy-3-(phenylcarbonyl)-2H-chromen-2-one
• 3-Benzoyl-7-methoxy-chromen-2-one
• NSC379520
• Oprea1_813737
• SCHEMBL51978
• MLS000595279
• CHEMBL1533108
• DTXSID40321660
• HMS2485N24
• STK716579
• AKOS002529059
• BS-5075
• NSC-379520
• NCGC00309297-01
• SMR000149802
• CS-0259767
• FT-0662604
• 2H-1-Benzopyran-2-one, 3-benzoyl-7-methoxy-
• AB00489350-08
• EN300-7417405
• A834697
• Z56887229

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9852	98.52%
Caco-2	+	0.7089	70.89%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	+	0.7714	77.14%
Subcellular localzation	Mitochondria	0.6090	60.90%
OATP2B1 inhibitior	-	0.8659	86.59%
OATP1B1 inhibitior	+	0.9347	93.47%
OATP1B3 inhibitior	+	1.0000	100.00%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.7324	73.24%
P-glycoprotein inhibitior	+	0.6888	68.88%
P-glycoprotein substrate	-	0.9036	90.36%
CYP3A4 substrate	-	0.5960	59.60%
CYP2C9 substrate	-	0.8346	83.46%
CYP2D6 substrate	-	0.8306	83.06%
CYP3A4 inhibition	-	0.7865	78.65%
CYP2C9 inhibition	+	0.5414	54.14%
CYP2C19 inhibition	-	0.7386	73.86%
CYP2D6 inhibition	-	0.9554	95.54%
CYP1A2 inhibition	+	0.9785	97.85%
CYP2C8 inhibition	-	0.5986	59.86%
CYP inhibitory promiscuity	-	0.5527	55.27%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9613	96.13%
Carcinogenicity (trinary)	Non-required	0.5625	56.25%
Eye corrosion	-	0.9286	92.86%
Eye irritation	+	0.6692	66.92%
Skin irritation	-	0.6612	66.12%
Skin corrosion	-	0.9723	97.23%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5555	55.55%
Micronuclear	+	0.8159	81.59%
Hepatotoxicity	-	0.5780	57.80%
skin sensitisation	-	0.9569	95.69%
Respiratory toxicity	-	0.6333	63.33%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	-	0.5901	59.01%
Acute Oral Toxicity (c)	III	0.6141	61.41%
Estrogen receptor binding	+	0.9347	93.47%
Androgen receptor binding	+	0.9602	96.02%
Thyroid receptor binding	-	0.5822	58.22%
Glucocorticoid receptor binding	+	0.7950	79.50%
Aromatase binding	+	0.8130	81.30%
PPAR gamma	+	0.7218	72.18%
Honey bee toxicity	-	0.9381	93.81%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9596	95.96%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	14125.4 nM	Potency	via CMAUP
CHEMBL2392	P06746	DNA polymerase beta	5011.9 nM	Potency	via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	28183.8 nM	Potency	via CMAUP
CHEMBL1293277	O15118	Niemann-Pick C1 protein	5623.4 nM	Potency	via CMAUP
CHEMBL1293294	P51151	Ras-related protein Rab-9A	3548.1 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1293294	P51151	Ras-related protein Rab-9A	96.32%	87.67%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.05%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.04%	86.33%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	92.82%	95.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.61%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.79%	99.23%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.18%	94.00%
CHEMBL2535	P11166	Glucose transporter	90.14%	98.75%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.36%	99.17%
CHEMBL4208	P20618	Proteasome component C5	88.01%	90.00%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	87.67%	81.11%
CHEMBL2581	P07339	Cathepsin D	86.68%	98.95%
CHEMBL4531	P17931	Galectin-3	85.84%	96.90%
CHEMBL3401	O75469	Pregnane X receptor	80.26%	94.73%

Plants that contains it

• Isodon serra

Cross-Links

• PubChem: 342533
• NPASS: NPC66705
• ChEMBL: CHEMBL1533108