APOCYNIN

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Search structure


Synonyms	4-hydroxy-3-methoxyacetophenone Acetovanillone Apocynin NSC-209524
Status
Molecule Category	UNKNOWN
UNII	B6J7B9UDTR
EPA CompTox	DTXSID7060097


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	DFYRUELUNQRZTB-UHFFFAOYSA-N
Smiles	COc1cc(C(C)=O)ccc1O
InChI	InChI=1S/C9H10O3/c1-6(10)7-3-4-8(11)9(5-7)12-2/h3-5,11H,1-2H3

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C9H10O3
Molecular Weight	166.18
AlogP	1.6
Hydrogen Bond Acceptor	3.0
Hydrogen Bond Donor	1.0
Number of Rotational Bond	2.0
Polar Surface Area	46.53
Molecular species	NEUTRAL
Aromatic Rings	1.0
Heavy Atoms	12.0

Assay Description	Organism	Bioactivity	Reference
Ability to protect microvascular damages in ischemia/reperfusion (in vivo) was determined by measuring the inhibition of leaky sites, 30-min after the start of reperfusion at 30 mg/kg	Cricetulus griseus	59.0 %
Inhibition of beta-hexosaminidase in anti-DNP IgE sensitized rat RBL2H3 cells at 100 uM after 10 mins	Rattus norvegicus	2.3 %
Antiinflammatory activity in LPS-stimulated mouse RAW264.7 cells assessed as inhibition of TNFalpha formation at 30 uM pretreated 1 hr before LPS challenge measured after 24 hrs by enzyme immunoassay	Mus musculus	-19.8 %
Antiinflammatory activity in LPS/IFN-gamma-stimulated mouse N9 cells assessed as inhibition of TNFalpha formation at 30 uM pretreated 1 hr before LPS/IFNgamma challenge measured after 24 hrs by enzyme immunoassay	Mus musculus	-22.6 %
Antioxidant activity against microvascular damage in hamster model of cheek pouch submitted to ischemia/reperfusion assessed as inhibition of leaky sites at 3 mg/kg treated by gavage route 30 mins before anesthesia measured after 30 mins of reperfusion by FITC-dextran based microscopy	Cricetinae	40.0 %
Inhibition of theophylline-stimulated melanogenesis in mouse B16-4A5 cells at 30 uM after 72 hrs	Mus musculus	20.2 %
Inhibition of theophylline-stimulated melanogenesis in mouse B16-4A5 cells at 10 uM after 72 hrs	Mus musculus	18.9 %
Inhibition of theophylline-stimulated melanogenesis in mouse B16-4A5 cells at 3 uM after 72 hrs	Mus musculus	17.5 %
Inhibition of theophylline-stimulated melanogenesis in mouse B16-4A5 cells at 1 uM after 72 hrs	Mus musculus	16.8 %
Toxicity in mouse B16-4A5 cells assessed as inhibition of cell proliferation at 30 uM in presence of 1 mM theophylline after 72 hrs by WST8 dye reduction assay	Mus musculus	8.8 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600)	Pseudomonas aeruginosa	-44.4 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600	Acinetobacter baumannii	9.5 %
Antibacterial activity against Pseudomonas aeruginosa PAO397 [PAO1 d(mexAB-oprM) d(mexCD-oprJ) d(mexEF-oprN) d(mexJKL) d(mexXY) d(opmH)] (CO-ADD:GN_211); MIC in CAMBH media using NBS plates, by OD(600)	Pseudomonas aeruginosa	-15.14 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging	Homo sapiens	-5.93 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	5.5 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.24 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.24 %

Cross References

Resources	Reference
ChEBI	2781
ChEMBL	CHEMBL346919
DrugBank	DB12618
FDA SRS	B6J7B9UDTR
KEGG	C11380
PDB	I75
PubChem	2214
SureChEMBL	SCHEMBL109514
ZINC	ZINC000000162515

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).