VIOLACEIN

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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 XAPNKXIRQFHCHN-QGOAFFKASA-N
Smiles Oc1ccc2[nH]cc(C3=C\C(=C\4/C(=O)Nc5ccccc45)\C(=O)N3)c2c1
InChI
InChI=1S/C20H13N3O3/c24-10-5-6-15-12(7-10)14(9-21-15)17-8-13(19(25)23-17)18-11-3-1-2-4-16(11)22-20(18)26/h1-9,21,24H,(H,22,26)(H,23,25)/b18-13+

Physicochemical Descriptors

Property Name Value
Molecular Formula C20H13N3O3
Molecular Weight 343.34
AlogP 1.87
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 4.0
Number of Rotational Bond 1.0
Polar Surface Area 94.22
Molecular species NEUTRAL
Aromatic Rings 3.0
Heavy Atoms 26.0
Assay Description Organism Bioactivity Reference
Inhibition of HCl/ethanol- induced gastric damage in Mus musculus (mouse) at 10 mg/kg, po, sd Mus musculus 85.0 %
Cytotoxicity against Homo sapiens (human) Hep2 cells Homo sapiens 2200.0 nM
Cytotoxicity against Macaca mulatta (Rhesus monkey) MA104 cells Macaca mulatta 2200.0 nM
Cytotoxicity against Homo sapiens (human) Vero cells Homo sapiens 2200.0 nM
Cytotoxicity against Macaca mulatta (Rhesus monkey) FRhK4 cells Macaca mulatta 2200.0 nM
Antiviral activity against Enterovirus C (Poliovirus) infected HeLa cells at 0.063 ug/ml Enterovirus C 56.0 %
Antitrypanosomal activity against trypomastigote of Trypanosoma cruzi Y infected in albino mouse assessed as reduction in parasitemia at 100 mg/kg, ip for 7 days Trypanosoma cruzi 4.0 %
Antiparasitic activity against Leishmania amazonensis MHOM/BR /77/LTB0016 promastigote at 460.8 uM Leishmania amazonensis 100.0 %
Antiparasitic activity against Leishmania amazonensis MHOM/BR /77/LTB0016 after 24 hr Leishmania amazonensis 4300.0 nM
Cytotoxicity against Homo sapiens (human) DLD1 cells after 24 to 48 hr by MTT assay Homo sapiens 1500.0 nM
Cytotoxicity against Homo sapiens (human) HCT116 cells after 24 to 48 hr by MTT assay Homo sapiens 1500.0 nM
Cytotoxicity against Homo sapiens (human) Caco2 cells after 24 to 48 hr by MTT assay Homo sapiens 1500.0 nM
Cytotoxicity against Mus musculus (mouse) EAT cells Mus musculus 5000.0 nM
Cytotoxicity against Homo sapiens (human) HT-29 cells after 24 to 48 hr by MTT assay Homo sapiens 1500.0 nM
Cytotoxicity against Homo sapiens (human) Lymphocyte Homo sapiens 10000.0 nM
Cytotoxicity against Homo sapiens (human) U937 cells Homo sapiens 1000.0 nM
Cytotoxicity against Homo sapiens (human) K562 cells Homo sapiens 1000.0 nM
Cytotoxicity against Cricetulus griseus V79 cells Cricetulus griseus 5000.0 nM
Cytotoxicity against Homo sapiens (human) HL60 cells Homo sapiens 800.0 nM
Cytotoxicity against Homo sapiens (human) NCI-H460 cells Homo sapiens 30.0 nM
Cytotoxicity against Homo sapiens (human) KM12 cells Homo sapiens 30.0 nM
Cytotoxicity against Homo sapiens (human) MOLT4 cells Homo sapiens 30.0 nM
Antimycobacterial activity against Mycobacterium tuberculosis H37Rv Mycobacterium tuberculosis H37Rv 128.0 ug ml-1 Antimycobacterial activity against Mycobacterium tuberculosis H37Rv Mycobacterium tuberculosis H37Rv 64.0 ug.mL-1
Antifeedant activity against Helicoverpa armigera at 1000 ppm Helicoverpa armigera 80.0 %
Insecticidal activity Spodoptera litura third-instar larva fed on 1000 ppm compound pre-treated castor leaf disks for 24 hr followed by larval maintenance on fresh castor leaves assessed as induction of abnormalities Spodoptera litura None
Insecticidal activity Spodoptera litura third-instar larva fed on 1000 ppm compound pre-treated castor leaf disks for 24 hr followed by larval maintenance on fresh castor leaves assessed as total mortality (Rvb = 8%) Spodoptera litura 99.1 %
Insecticidal activity Spodoptera litura third-instar larva fed on 500 ppm compound pre-treated castor leaf disks for 24 hr followed by larval maintenance on fresh castor leaves assessed as total mortality (Rvb = 8%) Spodoptera litura 89.58 %
Insecticidal activity Spodoptera litura third-instar larva fed on 250 ppm compound pre-treated castor leaf disks for 24 hr followed by larval maintenance on fresh castor leaves assessed as total mortality (Rvb = 8%) Spodoptera litura 77.99 %
Insecticidal activity Spodoptera litura third-instar larva fed on 125 ppm compound pre-treated castor leaf disks for 24 hr followed by larval maintenance on fresh castor leaves assessed as total mortality (Rvb = 8%) Spodoptera litura 51.11 %
Pupicidal activity Spodoptera litura third-instar larva fed on 1000 ppm compound pre-treated castor leaf disks for 24 hr followed by larval maintenance on fresh castor leaves until pupae formation assessed as pupal mortality (Rvb = 8.0 +/- 4.47%) Spodoptera litura 22.0 %
Pupicidal activity Spodoptera litura third-instar larva fed on 500 ppm compound pre-treated castor leaf disks for 24 hr followed by larval maintenance on fresh castor leaves until pupae formation assessed as pupal mortality (Rvb = 8.0 +/- 4.47%) Spodoptera litura 20.7 %
Pupicidal activity Spodoptera litura third-instar larva fed on 250 ppm compound pre-treated castor leaf disks for 24 hr followed by larval maintenance on fresh castor leaves until pupae formation assessed as pupal mortality (Rvb = 8.0 +/- 4.47%) Spodoptera litura 24.0 %
Pupicidal activity Spodoptera litura third-instar larva fed on 125 ppm compound pre-treated castor leaf disks for 24 hr followed by larval maintenance on fresh castor leaves until pupae formation assessed as pupal mortality (Rvb = 8.0 +/- 4.47%) Spodoptera litura 22.0 %
Larvicidal activity Spodoptera litura third-instar larva fed on compound pre-treated castor leaf disks for 24 hr followed by larval maintenance on fresh castor leaves assessed as insect mortality measured after 96 hr Spodoptera litura 2016.71 ppm Larvicidal activity Spodoptera litura third-instar larva fed on compound pre-treated castor leaf disks for 24 hr followed by larval maintenance on fresh castor leaves assessed as insect mortality measured after 96 hr Spodoptera litura 255.06 ppm
Larvicidal activity Spodoptera litura third-instar larva fed on 1000 ppm compound pre-treated castor leaf disks for 24 hr followed by larval maintenance on fresh castor leaves assessed as insect mortality measured after 96 hr Spodoptera litura 77.1 %
Larvicidal activity Spodoptera litura third-instar larva fed on 500 ppm compound pre-treated castor leaf disks for 24 hr followed by larval maintenance on fresh castor leaves assessed as insect mortality measured after 96 hr Spodoptera litura 68.88 %
Larvicidal activity Spodoptera litura third-instar larva fed on 250 ppm compound pre-treated castor leaf disks for 24 hr followed by larval maintenance on fresh castor leaves assessed as insect mortality measured after 96 hr Spodoptera litura 53.99 %
Larvicidal activity Spodoptera litura third-instar larva fed on 125 ppm compound pre-treated castor leaf disks for 24 hr followed by larval maintenance on fresh castor leaves assessed as insect mortality measured after 96 hr Spodoptera litura 29.11 %
Antifeedant activity against Spodoptera litura third-instar larva fed on compound pre-treated castor leaf disks measured after 24 hr by leaf-disk no-choice method (Rvb = 2.09 +/- 0.94%) Spodoptera litura 3649.91 ppm Antifeedant activity against Spodoptera litura third-instar larva fed on compound pre-treated castor leaf disks measured after 24 hr by leaf-disk no-choice method (Rvb = 2.09 +/- 0.94%) Spodoptera litura 392.25 ppm
Antifeedant activity against Spodoptera litura third-instar larva fed on 1000 ppm compound pre-treated castor leaf disks measured after 24 hr by leaf-disk no-choice method (Rvb = 2.09 +/- 0.94%) Spodoptera litura 72.46 %
Antifeedant activity against Spodoptera litura third-instar larva fed on 500 ppm compound pre-treated castor leaf disks measured after 24 hr by leaf-disk no-choice method (Rvb = 2.09 +/- 0.94%) Spodoptera litura 55.16 %
Antifeedant activity against Spodoptera litura third-instar larva fed on 250 ppm compound pre-treated castor leaf disks measured after 24 hr by leaf-disk no-choice method (Rvb = 2.09 +/- 0.94%) Spodoptera litura 39.69 %
Antifeedant activity against Spodoptera litura third-instar larva fed on 125 ppm compound pre-treated castor leaf disks measured after 24 hr by leaf-disk no-choice method (Rvb = 2.09 +/- 0.94%) Spodoptera litura 28.66 %

Cross References

Resources Reference
ChEMBL CHEMBL1652263
PubChem 9928039
SureChEMBL SCHEMBL151999
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