Synonyms
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 ...

Structure

InChI Key ZIUSSTSXXLLKKK-KOBPDPAPSA-N
Smiles COc1cc(\C=C\C(=C\C(=O)\C=C\c2ccc(O)c(OC)c2)\O)ccc1O
InChI
InChI=1S/C21H20O6/c1-26-20-11-14(5-9-18(20)24)3-7-16(22)13-17(23)8-4-15-6-10-19(25)21(12-15)27-2/h3-13,22,24-25H,1-2H3/b7-3+,8-4+,16-13-

Physicochemical Descriptors

Property Name Value
Molecular Formula C21H20O6
Molecular Weight 368.38
AlogP 3.57
Hydrogen Bond Acceptor 6.0
Hydrogen Bond Donor 3.0
Number of Rotational Bond 7.0
Polar Surface Area 96.22
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 27.0
Assay Description Organism Bioactivity Reference
Cytotoxicity against Homo sapiens (human) SW480 cell by MTT assay Homo sapiens 18130.0 nM
Cytotoxicity against Homo sapiens (human) A549 cell by MTT assay Homo sapiens 24590.0 nM
Cytotoxicity against Homo sapiens (human) MCF7 cell by MTT assay Homo sapiens 21390.0 nM
Cytotoxicity against Homo sapiens (human) HeLa cell by MTT assay Homo sapiens 17310.0 nM
Cytotoxicity against Homo sapiens (human) HCT116 cells by MTT assay Homo sapiens 10000.0 nM
Cytotoxicity against Homo sapiens (human) SKBR3 cells by MTT assay Homo sapiens 27000.0 nM
Cytotoxicity against Homo sapiens (human) HeLa cells by MTT assay Homo sapiens 17000.0 nM
Cytotoxicity against Homo sapiens (human) H1299 cells assessed as cell viability at 25 uM by MTT assay Homo sapiens 44.7 %
Cytotoxicity against Homo sapiens (human) H1299 cells assessed as cell viability at 10 uM by MTT assay Homo sapiens 62.4 %
Cytotoxicity against Homo sapiens (human) H1299 cells assessed as cell viability at 5 uM by MTT assay Homo sapiens 86.1 %
Cytotoxicity against Homo sapiens (human) A375 cells assessed as cell viability at 25 uM by MTT assay Homo sapiens 50.2 %
Cytotoxicity against Homo sapiens (human) A375 cells assessed as cell viability at 10 uM by MTT assay Homo sapiens 72.3 %
Cytotoxicity against Homo sapiens (human) A375 cells assessed as cell viability at 5 uM by MTT assay Homo sapiens 92.0 %
Cytotoxicity against Homo sapiens (human) HCT116 cells assessed as cell viability at 25 uM by MTT assay Homo sapiens 22.4 %
Cytotoxicity against Homo sapiens (human) HCT116 cells assessed as cell viability at 10 uM by MTT assay Homo sapiens 49.6 %
Cytotoxicity against Homo sapiens (human) HCT116 cells assessed as cell viability at 5 uM by MTT assay Homo sapiens 61.6 %
Cytotoxicity against Homo sapiens (human) SKBR3 cells assessed as cell viability at 25 uM by MTT assay Homo sapiens 56.5 %
Cytotoxicity against Homo sapiens (human) SKBR3 cells assessed as cell viability at 10 uM by MTT assay Homo sapiens 74.0 %
Cytotoxicity against Homo sapiens (human) SKBR3 cells assessed as cell viability at 5 uM by MTT assay Homo sapiens 53.7 %
Cytotoxicity against Homo sapiens (human) HeLa cells assessed as cell viability at 5 uM by MTT assay Homo sapiens 78.3 %
Cytotoxicity against Homo sapiens (human) HeLa cells assessed as cell viability at 10 uM by MTT assay Homo sapiens 53.7 %
Cytotoxicity against Homo sapiens (human) HeLa cells assessed as cell viability at 25 uM by MTT assay Homo sapiens 28.0 %
Antioxidant activity assessed as DPPH scavenging activity after 30 min by spectrophotometry None None
Anti-inflammatory activity in Mus musculus (mouse) RAW264.7 cells assessed as inhibition of IFN-gamma/LPS-induced nitric oxide production after 17 to 20 hr by Griess assay Mus musculus 21580.0 nM
Down regulation of rhlA expression in Pseudomonas aeruginosa PAO1 at 3 ug/mL by microarray gene expression analysis Pseudomonas aeruginosa PAO1 None
Down regulation of lasI expression in Pseudomonas aeruginosa PAO1 at 3 ug/mL by microarray gene expression analysis Pseudomonas aeruginosa PAO1 None
Down regulation of phzD expression in Pseudomonas aeruginosa PAO1 at 3 ug/mL by microarray gene expression analysis Pseudomonas aeruginosa PAO1 None
Effect on QS system related genes in Pseudomonas aeruginosa PAO1 at 3 ug/mL by microarray gene expression analysis Pseudomonas aeruginosa PAO1 None
Antimicrobial activity against Pseudomonas aeruginosa PAO1 infected in Arabidopsis thaliana Col-0 assessed as change in bacterial count in presence of AHL/3-oxo-HSL Pseudomonas aeruginosa PAO1 None
Antimicrobial activity against Pseudomonas aeruginosa PAO1 infected in Arabidopsis thaliana Col-0 assessed as inhibition of biofilm formation in roots at 3 ug/mL measured 7 days post dose Pseudomonas aeruginosa PAO1 None
Antimicrobial activity against Pseudomonas aeruginosa PAO1 infected in Arabidopsis thaliana Col-0 assessed as protection against infection of roots at 3 ug/mL measured 7 days post dose Pseudomonas aeruginosa PAO1 None
Down regulation of QS system in Pseudomonas aeruginosa PAO1 assessed as reduction in total homoserine lactone production at 5 ug/mL by HPLC relative to untreated control Pseudomonas aeruginosa PAO1 3.0
Down regulation of QS system in Pseudomonas aeruginosa PAO1 assessed as reduction in C4-HSL production at 1 ug/mL by HPLC Pseudomonas aeruginosa PAO1 2.0 %
Down regulation of QS system in Pseudomonas aeruginosa PAO1 assessed as reduction in 3-oxo-C12-HSL production at 1 ug/mL by HPLC Pseudomonas aeruginosa PAO1 25.0 %
Down regulation of virulence factor production in Pseudomonas aeruginosa PAO1 assessed as reduction in elastase production at 1 to 5 ug/mL relative to untreated control Pseudomonas aeruginosa PAO1 2.0
Down regulation of virulence factor production in Pseudomonas aeruginosa PAO1 assessed as reduction in protease production at 1 to 5 ug/mL relative to untreated control Pseudomonas aeruginosa PAO1 2.0
Down regulation of virulence factor production in Pseudomonas aeruginosa PAO1 assessed as reduction in pyocyanin production at 1.5 to 3 ug/mL Pseudomonas aeruginosa PAO1 60.0 %
Inhibition of biofilm formation of Pseudomonas aeruginosa PAO1 at 2 to 3 ug/mL by confocal scanning laser microscopy Pseudomonas aeruginosa PAO1 None
Inhibition of biofilm formation of Pseudomonas aeruginosa PAO1 at 1.5 to 3 ug/mL by crystal violet staining method Pseudomonas aeruginosa PAO1 None
Growth inhibition of Pseudomonas aeruginosa PAO1 planktonic forms Pseudomonas aeruginosa PAO1 30.0 ug.mL-1
Growth inhibition of Pseudomonas aeruginosa PAO1 planktonic forms at >5 ug/mL Pseudomonas aeruginosa PAO1 None
Cytotoxicity against Mus musculus (mouse) EAC assessed as cell viability by trypan blue exclusion assay Mus musculus 3.4 mM Cytotoxicity against Mus musculus (mouse) EAC assessed as cell viability by trypan blue exclusion assay Mus musculus 4.8 mM Cytotoxicity against Mus musculus (mouse) EAC assessed as cell viability by trypan blue exclusion assay Mus musculus 100.0 mM
Cytotoxicity against Homo sapiens (human) K562 cells Homo sapiens 54300.0 nM
Cytotoxicity against Homo sapiens (human) SK-N-MC cells after 72 hr by MTT assay Homo sapiens 57400.0 nM
Cytotoxicity against Homo sapiens (human) K562 cells after 72 hr by MTT assay Homo sapiens 49200.0 nM
Inhibition of Ovis aries (sheep) brain tubulin polymerization assessed as microtubule assembly after 15 min by measuring turbidity based spectroscopic analysis Ovis aries 26600.0 nM
Antiproliferative activity against Homo sapiens (human) MCF7 cells Homo sapiens 12000.0 nM
Antiproliferative activity against Homo sapiens (human) HeLa cells Homo sapiens 13800.0 nM
Inhibition of Homo sapiens (human) topoisomerase 1 assessed as relaxation of supercoiled DNA up to 25 uM by agarose gel electrophoresis Homo sapiens None
Inhibition of Homo sapiens (human) topoisomerase 2 assessed as decatenation of KDNA by agarose gel electrophoresis Homo sapiens 15000.0 nM
Inhibition of Homo sapiens (human) topoisomerase 1 assessed as production of nicked DNA up to 25 uM by agarose gel electrophoresis Homo sapiens None
Cytotoxicity against Sus scrofa (pig) LLC-PK1 cells up to 25 uM by neutral red staining Sus scrofa None
Cytotoxicity against Chlorocebus aethiops (African green monkey) Vero cells up to 25 uM by neutral red staining Chlorocebus aethiops None
Cytotoxicity against Homo sapiens (human) SKOV3 cells up to 25 uM by neutral red staining Homo sapiens None
Cytotoxicity against Homo sapiens (human) SK-MEL cells by neutral red staining Homo sapiens 13750.0 nM
Cytotoxicity against Homo sapiens (human) KB cells by neutral red staining Homo sapiens 25000.0 nM
Cytotoxicity against Homo sapiens (human) BT549 cells by neutral red staining Homo sapiens 10500.0 nM
Fungicidal activity against Blumeria graminis infected first-leaf stage of barley plant at 125 mg/l applied as spray under green house conditions relative to control Blumeria graminis 0.0 %
Fungicidal activity against Blumeria graminis infected first-leaf stage of barley plant at 250 mg/l applied as spray under green house conditions relative to control Blumeria graminis 0.0 %
Fungicidal activity against Blumeria graminis infected first-leaf stage of barley plant at 500 mg/l applied as spray under green house conditions relative to control Blumeria graminis 0.0 %
Fungicidal activity against Blumeria graminis infected first-leaf stage of barley plant at 1000 mg/l applied as spray under green house conditions relative to control Blumeria graminis 0.0 %
Fungicidal activity against Puccinia recondita infected first leaf stage of wheat plant at 125 mg/l applied as spray after 10 days under green house conditions relative to control Puccinia recondita 63.0 %
Fungicidal activity against Puccinia recondita infected first leaf stage of wheat plant at 250 mg/l applied as spray after 10 days under green house conditions relative to control Puccinia recondita 76.0 %
Fungicidal activity against Puccinia recondita infected first leaf stage of wheat plant at 500 mg/l applied as spray after 10 days under green house conditions relative to control Puccinia recondita 100.0 %
Fungicidal activity against Puccinia recondita infected first leaf stage of wheat plant at 1000 mg/l applied as spray after 10 days under green house conditions relative to control Puccinia recondita 100.0 %
Fungicidal activity against Phytophthora infestans infected second leaf-stage of tomato plant at 125 mg/l applied as spray after 4 days under green house conditions relative to control Phytophthora infestans 57.0 %
Fungicidal activity against Phytophthora infestans infected second leaf-stage of tomato plant at 250 mg/l applied as spray after 4 days under green house conditions relative to control Phytophthora infestans 85.0 %
Fungicidal activity against Phytophthora infestans infected second leaf-stage of tomato plant at 500 mg/l applied as spray after 4 days under green house conditions relative to control Phytophthora infestans 100.0 %
Fungicidal activity against Phytophthora infestans infected second leaf-stage of tomato plant at 1000 mg/l applied as spray after 4 days under green house conditions relative to control Phytophthora infestans 100.0 %
Fungicidal activity against Botryotinia fuckeliana infected first-leaf stage of cucumber plant at 125 mg/l applied as spray after 4 to 5 days under green house conditions relative to control Botryotinia fuckeliana 0.0 %
Fungicidal activity against Botryotinia fuckeliana infected first-leaf stage of cucumber plant at 250 mg/l applied as spray after 4 to 5 days under green house conditions relative to control Botryotinia fuckeliana 15.0 %
Fungicidal activity against Botryotinia fuckeliana infected first-leaf stage of cucumber plant at 500 mg/l applied as spray after 4 to 5 days under green house conditions relative to control Botryotinia fuckeliana 40.0 %
Fungicidal activity against Botryotinia fuckeliana infected first-leaf stage of cucumber plant at 1000 mg/l applied as spray after 4 to 5 days under green house conditions relative to control Botryotinia fuckeliana 70.0 %
Fungicidal activity against Rhizoctonia solani infected in third leaf stage of rice plant at 125 mg/l applied as spray after 5 days under green house conditions relative to control Rhizoctonia solani 26.0 %
Fungicidal activity against Rhizoctonia solani infected in third leaf stage of rice plant at 250 mg/l applied as spray after 5 days under green house conditions relative to control Rhizoctonia solani 45.0 %
Fungicidal activity against Rhizoctonia solani infected in third leaf stage of rice plant at 1000 mg/l applied as spray after 5 days under green house conditions relative to control Rhizoctonia solani 85.0 %
Fungicidal activity against Rhizoctonia solani infected in third leaf stage of rice plant at 500 mg/l applied as spray after 5 days under green house conditions relative to control Rhizoctonia solani 63.0 %
Fungicidal activity against Magnaporthe grisea infected second leaf stage of rice plant at 125 mg/l applied as spray after 5 days under green house conditions relative to control Magnaporthe grisea 0.0 %
Fungicidal activity against Magnaporthe grisea infected second leaf stage of rice plant at 250 mg/l applied as spray after 5 days under green house conditions relative to control Magnaporthe grisea 0.0 %
Fungicidal activity against Magnaporthe grisea infected second leaf stage of rice plant at 500 mg/l applied as spray after 5 days under green house conditions relative to control Magnaporthe grisea 0.0 %
Fungicidal activity against Magnaporthe grisea infected second leaf stage of rice plant at 1000 mg/l applied as spray after 5 days under green house conditions relative to control Magnaporthe grisea 0.0 %
Cytotoxicity against Homo sapiens (human) MCF7 cells assessed as cell viability at 20 ug/ml by trypan blue assay Homo sapiens 19.0 %
Cytotoxicity against Chlorocebus aethiops (African green monkey) Vero cells assessed as cell viability at 20 ug/ml by trypan blue assay Chlorocebus aethiops 24.0 %
Cytotoxicity against Homo sapiens (human) WI38 cells assessed as cell viability at 20 ug/ml by trypan blue assay Homo sapiens 51.0 %
Cytotoxicity against Homo sapiens (human) HepG2 cells assessed as cell viability at 20 ug/ml by trypan blue assay Homo sapiens 18.0 %
Anticancer activity against Homo sapiens (human) A549 cells assessed as inhibition of cell viability after 72 hr by MTT assay Homo sapiens 22000.0 nM
Anticancer activity against Homo sapiens (human) HepG2 cells assessed as inhibition of cell viability after 72 hr by MTT assay Homo sapiens 16000.0 nM
Anticancer activity against Homo sapiens (human) HeLa cells assessed as inhibition of cell viability after 72 hr by MTT assay Homo sapiens 17000.0 nM
Anticancer activity against Homo sapiens (human) A431 cells assessed as inhibition of cell viability after 72 hr by MTT assay Homo sapiens 22000.0 nM
Anticancer activity against Homo sapiens (human) MCF7 cells assessed as inhibition of cell viability after 72 hr by MTT assay Homo sapiens 26000.0 nM

Cross References

Resources Reference
ChEMBL CHEMBL116438
PubChem 5281767
SureChEMBL SCHEMBL242412