1,8-NAPHTHALIC ANHYDRIDE


Synonyms	Benzo[De]Isochromene-1,3-Dione
UNII	32RS852X55
Source	Gaulton A, Kale N, van Westen GJ, Bellis LJ, Bento AP, Davies M, Hersey A, Papadatos G, Forster M, Wege P, Overington JP. A large-scale crop protection bioassay data set. Sci Data. 2015 Jul 7;2:150032. Read more ...


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

Structure


InChI Key	GRSMWKLPSNHDHA-UHFFFAOYSA-N
Smiles	O=C1OC(=O)c2cccc3cccc1c23
InChI	InChI=1S/C12H6O3/c13-11-8-5-1-3-7-4-2-6-9(10(7)8)12(14)15-11/h1-6H

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C12H6O3
Molecular Weight	198.17
AlogP	2.21
Hydrogen Bond Acceptor	3.0
Hydrogen Bond Donor	0.0
Number of Rotational Bond	0.0
Polar Surface Area	43.37
Molecular species	None
Aromatic Rings	2.0
Heavy Atoms	15.0

Assay Description	Organism	Bioactivity
Antioxidant activity assessed as DPPH radical scavenging activity	None	1773800.0 nM
Effect on pyruvate content in Zea mays (maize) endosperms assessed per gram of fresh weight at 0.2 % w/w after 10 days (Rvb = 11.4 umol)	Zea mays	11.2 umol
Effect on pyruvate content in Zea mays (maize) roots assessed per gram of fresh weight at 0.2 % w/w after 10 days (Rvb = 13.3 umol)	Zea mays	13.0 umol
Effect on pyruvate content in Zea mays (maize) shoot assessed per gram of fresh weight at 0.2 % w/w after 10 days (Rvb = 18.4 umol)	Zea mays	16.2 umol
Decrease of imazaquin-induced increase of pyruvate content in Zea mays (maize) assessed per gram of fresh weight at 0.2 % w/w after 10 days	Zea mays	None
Effect on pyruvate content in Zea mays (maize) embryos assessed per gram of fresh weight at 0.2 % w/w after 10 days (Rvb = 8.5 umol)	Zea mays	8.0 umol
Decrease of bensulfuron-methyl-induced increase of pyruvate content in Zea mays (maize) assessed per gram of fresh weight at 0.2 % w/w after 10 days	Zea mays	None
Increase of acetolactate synthase activity in Zea mays (maize) root	Zea mays	30.0 %
Increase of acetolactate synthase activity in Zea mays (maize) shoot	Zea mays	24.0 %
Increase of acetyl CoA carboxylase activity in Zea mays (maize) at 0.2 % w/w after 15 min relative to control	Zea mays	216.0 %
Increase of acetolactate synthase activity in Zea mays (maize) at 0.2 % w/w after 15 min relative to control	Zea mays	31.9 %
Protection against imazaquin-induced growth inhibition of Zea mays (maize) assessed as safening index at 0.05 to 0.4 % w/w treated 1 to 14 days before imazaquin challenge measured after 3 weeks relative to untreated control	Zea mays	5.1
Protection against bensulfuron-methyl-induced growth inhibition of Zea mays (maize) assessed as safening index at 0.05 to 0.4 % w/w treated 1 to 14 days before bensulfuron-methyl challenge measured after 3 weeks relative to untreated control	Zea mays	303.0

Cross References

Resources	Reference
ChEMBL	CHEMBL316059
FDA SRS	32RS852X55
PubChem	6693
SureChEMBL	SCHEMBL30415
ZINC	ZINC08457049

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).

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).