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Violacein

AlkaPlorer ID: AK325315

Synonym: None

IUPAC Name: 3-[2-hydroxy-5-(5-hydroxy-1H-indol-3-yl)-1H-pyrrol-3-yl]indol-2-one

Structure

SMILES: OC1=NC(C2=CNC3=CC=C(O)C=C23)=C/C1=C1\C(O)=NC2=CC=CC=C12

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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+

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InChIKey: XAPNKXIRQFHCHN-QGOAFFKASA-N

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Properties Information

Molecule Weight: 343.34200000000004

TPSA？: 101.2

MolLogP？: 4.239900000000001

Number of H-Donors: 4

Number of H-Acceptors: 3

RingCount: 5

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Chlorocebus sabaeus Vero IC50 2200.0 nM 10.1007/s00044-011-9654-9
Cricetulus griseus V79 IC50 5000.0 nM 10.1007/s00044-011-9654-9
Enterovirus C Enterovirus C Inhibition 56.0 % 10.1007/s00044-011-9654-9
Helicoverpa armigera Helicoverpa armigera AFI 80.0 % 10.1016/j.jssas.2011.10.002
Homo sapiens Caco-2 IC50 1500.0 nM 10.1007/s00044-011-9654-9
Homo sapiens DLD-1 IC50 1500.0 nM 10.1007/s00044-011-9654-9
Homo sapiens HCT-116 IC50 1500.0 nM 10.1007/s00044-011-9654-9
Homo sapiens HEp-2 IC50 2200.0 nM 10.1007/s00044-011-9654-9
Homo sapiens HL-60 IC50 800.0 nM 10.1007/s00044-011-9654-9
Homo sapiens HT-29 IC50 1500.0 nM 10.1007/s00044-011-9654-9
Homo sapiens K562 IC50 1000.0 nM 10.1007/s00044-011-9654-9
Homo sapiens KM12 GI50 30.0 nM 10.1007/s00044-011-9654-9
Homo sapiens MOLT-4 GI50 30.0 nM 10.1007/s00044-011-9654-9
Homo sapiens NCI-H460 GI50 30.0 nM 10.1007/s00044-011-9654-9
Homo sapiens U-937 IC50 1000.0 nM 10.1007/s00044-011-9654-9
Leishmania amazonensis Leishmania amazonensis EC50 4300.0 nM 10.1007/s00044-011-9654-9
Leishmania amazonensis Leishmania amazonensis Inhibition 100.0 % 10.1007/s00044-011-9654-9
Mus musculus Mus musculus Inhibition 85.0 % 10.1007/s00044-011-9654-9
Mycobacterium tuberculosis Mycobacterium tuberculosis MBC 128.0 ug ml-1 10.1007/s00044-011-9654-9
Mycobacterium tuberculosis Mycobacterium tuberculosis MIC 64.0 ug.mL-1 10.1007/s00044-011-9654-9
Plasmodium chabaudi Plasmodium chabaudi Inhibition 3.58 % 10.1128/aac.00693-08
Plasmodium chabaudi Plasmodium chabaudi Inhibition 12.04 % 10.1128/aac.00693-08
Plasmodium chabaudi Plasmodium chabaudi Inhibition 20.42 % 10.1128/aac.00693-08
Plasmodium chabaudi Plasmodium chabaudi Inhibition 33.23 % 10.1128/aac.00693-08
Plasmodium chabaudi Plasmodium chabaudi Inhibition 39.25 % 10.1128/aac.00693-08
Plasmodium chabaudi Plasmodium chabaudi Inhibition 48.85 % 10.1128/aac.00693-08
Plasmodium chabaudi Plasmodium chabaudi Inhibition 50.1 % 10.1128/aac.00693-08
Plasmodium chabaudi Plasmodium chabaudi Inhibition 56.48 % 10.1128/aac.00693-08
Plasmodium chabaudi Plasmodium chabaudi Inhibition 59.0 % 10.1128/aac.00693-08
Plasmodium chabaudi Plasmodium chabaudi Inhibition 64.89 % 10.1128/aac.00693-08
Plasmodium chabaudi Plasmodium chabaudi Inhibition 75.4 % 10.1128/aac.00693-08
Plasmodium chabaudi Plasmodium chabaudi Inhibition 75.73 % 10.1128/aac.00693-08
Plasmodium chabaudi Plasmodium chabaudi Inhibition 82.12 % 10.1128/aac.00693-08
Plasmodium chabaudi Plasmodium chabaudi Inhibition 84.67 % 10.1128/aac.00693-08
Plasmodium chabaudi Plasmodium chabaudi Inhibition 86.9 % 10.1128/aac.00693-08
Plasmodium chabaudi Plasmodium chabaudi Inhibition nan % 10.1128/aac.00693-08
Plasmodium chabaudi Plasmodium chabaudi Survival 10.0 % 10.1128/aac.00693-08
Plasmodium chabaudi Plasmodium chabaudi Survival 14.0 % 10.1128/aac.00693-08
Plasmodium chabaudi Plasmodium chabaudi Survival 80.0 % 10.1128/aac.00693-08
Plasmodium falciparum Plasmodium falciparum IC50 630.0 nM 10.1128/aac.00693-08
Plasmodium falciparum Plasmodium falciparum IC50 850.0 nM 10.1128/aac.00693-08
Plasmodium falciparum Plasmodium falciparum Inhibition nan % 10.1128/aac.00693-08
Spodoptera litura Spodoptera litura Activity nan None 10.1016/j.jssas.2011.10.002
Spodoptera litura Spodoptera litura AFI 28.66 % 10.1016/j.jssas.2011.10.002
Spodoptera litura Spodoptera litura AFI 39.69 % 10.1016/j.jssas.2011.10.002
Spodoptera litura Spodoptera litura AFI 55.16 % 10.1016/j.jssas.2011.10.002
Spodoptera litura Spodoptera litura AFI 72.46 % 10.1016/j.jssas.2011.10.002
Spodoptera litura Spodoptera litura LC50 255.06 ppm 10.1016/j.jssas.2011.10.002
Spodoptera litura Spodoptera litura LC50 392.25 ppm 10.1016/j.jssas.2011.10.002
Spodoptera litura Spodoptera litura LC90 2016.71 ppm 10.1016/j.jssas.2011.10.002
Spodoptera litura Spodoptera litura LC90 3649.91 ppm 10.1016/j.jssas.2011.10.002
Spodoptera litura Spodoptera litura mortality 20.7 % 10.1016/j.jssas.2011.10.002
Spodoptera litura Spodoptera litura mortality 22.0 % 10.1016/j.jssas.2011.10.002
Spodoptera litura Spodoptera litura mortality 24.0 % 10.1016/j.jssas.2011.10.002
Spodoptera litura Spodoptera litura mortality 29.11 % 10.1016/j.jssas.2011.10.002
Spodoptera litura Spodoptera litura mortality 51.11 % 10.1016/j.jssas.2011.10.002
Spodoptera litura Spodoptera litura mortality 53.99 % 10.1016/j.jssas.2011.10.002
Spodoptera litura Spodoptera litura mortality 68.88 % 10.1016/j.jssas.2011.10.002
Spodoptera litura Spodoptera litura mortality 77.1 % 10.1016/j.jssas.2011.10.002
Spodoptera litura Spodoptera litura mortality 77.99 % 10.1016/j.jssas.2011.10.002
Spodoptera litura Spodoptera litura mortality 89.58 % 10.1016/j.jssas.2011.10.002
Spodoptera litura Spodoptera litura mortality 99.1 % 10.1016/j.jssas.2011.10.002
Trypanosoma cruzi Trypanosoma cruzi Inhibition 4.0 % 10.1007/s00044-011-9654-9
None ADMET Activity nan None 10.1128/aac.00693-08
None ADMET IC50 2200.0 nM 10.1007/s00044-011-9654-9
None ADMET IC50 10000.0 nM 10.1007/s00044-011-9654-9
None NON-PROTEIN TARGET IC50 5000.0 nM 10.1007/s00044-011-9654-9

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT023254 O=C(O)c1[nH]c(-c2c[nH]c3ccc(O)cc23)cc1-c1c(O)[nH]c2ccccc12>>O=C1NC(c2c[nH]c3ccc(O)cc23)=C/C1=C1\C(=O)Nc2ccccc21 RXN-13343
AKRT023256 O=C(O)c1[nH]c(-c2c[nH]c3ccc(O)cc23)cc1-c1c[nH]c2ccccc12>>O=C1NC(c2c[nH]c3ccc(O)cc23)=C/C1=C1\C(=O)Nc2ccccc21 49720