2-Anilino-1,4-naphthoquinone
AlkaPlorer ID: AK003748
Synonym: 2-(Phenylamino)-1,4-naphthalenedione, 4-Hydroxy-2-(phenylimino)-1(2H)-naphthalenone, Lutine
IUPAC Name: 2-anilinonaphthalene-1,4-dione
Structure
SMILES: O=C1C=C(NC2=CC=CC=C2)C(=O)C2=C1C=CC=C2
InChI: InChI=1S/C16H11NO2/c18-15-10-14(17-11-6-2-1-3-7-11)16(19)13-9-5-4-8-12(13)15/h1-10,17H
InChIKey: OPECBHGHSFBITB-UHFFFAOYSA-N
Reference
PubChem CID: 81124
CAS: 6628-97-3
SuperNatural Ⅲ: SN0271508
NPASS: NPC192533
COCONUT: CNP0288378
Source
| Species | Genus | Family | Order | Class | Phylum | Kingdom | Domain |
|---|---|---|---|---|---|---|---|
| Lygodium japonicum | Lygodium | Lygodiaceae | Schizaeales | Polypodiopsida | Streptophyta | Viridiplantae | Eukaryota |
| Reseda luteola | Reseda | Resedaceae | Brassicales | Magnoliopsida | Streptophyta | Viridiplantae | Eukaryota |
Properties Information
Molecule Weight: 249.269
TPSA？: 46.17
MolLogP？: 3.061600000000001
Number of H-Donors: 1
Number of H-Acceptors: 3
RingCount: 3
Activities Information
| Organism | Target Name | Standard Type | Standard Value | Standard Units | doi |
|---|---|---|---|---|---|
| Chlorocebus sabaeus | Vero | IC50 | 10000.0 | nM | 10.1016/j.bmc.2014.07.030 |
| Enterobacter cloacae | Enterobacter cloacae | MIC | 250.0 | ug.mL-1 | 10.1016/j.ejmech.2016.10.034 |
| Enterococcus faecalis | Enterococcus faecalis | MIC | nan | None | 10.1016/j.ejmech.2016.10.034 |
| Escherichia coli | Escherichia coli | MIC | 250.0 | ug.mL-1 | 10.1016/j.ejmech.2016.10.034 |
| Escherichia coli K-12 | Beta-lactamase AmpC | Potency | 3162.3 | nM | None |
| Giardia intestinalis | Putative fructose-1,6-bisphosphate aldolase | Potency | 3539.7 | nM | None |
| Homo sapiens | Aldehyde dehydrogenase 1A1 | Potency | 39810.7 | nM | None |
| Homo sapiens | Ataxin-2 | Potency | 9466.2 | nM | None |
| Homo sapiens | ATPase family AAA domain-containing protein 5 | Potency | 2908.1 | nM | None |
| Homo sapiens | Bromodomain adjacent to zinc finger domain protein 2B | Potency | 7943.3 | nM | None |
| Homo sapiens | Cellular tumor antigen p53 | Potency | 79432.8 | nM | None |
| Homo sapiens | Chromobox protein homolog 1 | Potency | 12589.3 | nM | None |
| Homo sapiens | DU-145 | EC50 | 4.0 | ug.mL-1 | 10.1016/j.ejmech.2010.10.006 |
| Homo sapiens | DU-145 | IC50 | 5520.0 | nM | 10.1016/j.bmc.2013.05.017 |
| Homo sapiens | Eyes absent homolog 2 | Potency | 6013.0 | nM | None |
| Homo sapiens | Geminin | Potency | 32642.7 | nM | None |
| Homo sapiens | HEK-293T | IC50 | 5600.0 | nM | 10.1016/j.bmcl.2021.128274 |
| Homo sapiens | HepG2 | Potency | 5011.9 | nM | None |
| Homo sapiens | Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 | Potency | 14125.4 | nM | None |
| Homo sapiens | HT-29 | IC50 | 31250.0 | nM | 10.1016/j.bmc.2013.05.017 |
| Homo sapiens | Huntingtin | Potency | 11220.2 | nM | None |
| Homo sapiens | Isocitrate dehydrogenase [NADP] cytoplasmic | Potency | 14581.0 | nM | None |
| Homo sapiens | Lethal(3)malignant brain tumor-like protein 1 | Potency | 2511.9 | nM | None |
| Homo sapiens | Lysine-specific demethylase 4A | Potency | 12589.3 | nM | None |
| Homo sapiens | MAP kinase ERK2 | Potency | 25118.9 | nM | None |
| Homo sapiens | MCF7 | EC50 | 2.6 | ug.mL-1 | 10.1016/j.ejmech.2010.10.006 |
| Homo sapiens | MCF7 | IC50 | 4400.0 | nM | 10.1016/j.bmcl.2021.128274 |
| Homo sapiens | MCF7 | Ratio EC50 | 0.08 | None | 10.1016/j.ejmech.2010.10.006 |
| Homo sapiens | MDA-MB-231 | IC50 | 5300.0 | nM | 10.1016/j.bmcl.2021.128274 |
| Homo sapiens | MDA-MB-231 | IC50 | 100000.0 | nM | 10.1016/j.bmc.2013.05.017 |
| Homo sapiens | Microphthalmia-associated transcription factor | AbsAC40_uM | 0.175 | uM | None |
| Homo sapiens | Microphthalmia-associated transcription factor | AbsAC40_uM | 0.189 | uM | None |
| Homo sapiens | Microphthalmia-associated transcription factor | AbsAC40_uM | 0.302 | uM | None |
| Homo sapiens | Microphthalmia-associated transcription factor | AbsAC40_uM | 0.323 | uM | None |
| Homo sapiens | Microphthalmia-associated transcription factor | AbsAC40_uM | 0.325 | uM | None |
| Homo sapiens | Microphthalmia-associated transcription factor | AbsAC40_uM | 0.337 | uM | None |
| Homo sapiens | Microphthalmia-associated transcription factor | AbsAC40_uM | 0.389 | uM | None |
| Homo sapiens | Microphthalmia-associated transcription factor | AbsAC40_uM | 0.394 | uM | None |
| Homo sapiens | Microphthalmia-associated transcription factor | AbsAC40_uM | 0.571 | uM | None |
| Homo sapiens | Microphthalmia-associated transcription factor | AbsAC40_uM | 0.74 | uM | None |
| Homo sapiens | microRNA 21 | Potency | 656.1 | nM | None |
| Homo sapiens | Microtubule-associated protein tau | Potency | 7079.5 | nM | None |
| Homo sapiens | Mothers against decapentaplegic homolog 3 | Potency | 3981.1 | nM | None |
| Homo sapiens | Mothers against decapentaplegic homolog 3 | Potency | 6513.1 | nM | None |
| Homo sapiens | Mothers against decapentaplegic homolog 3 | Potency | 20596.2 | nM | None |
| Homo sapiens | MRC5 | IC50 | 100000.0 | nM | 10.1016/j.ejmech.2015.11.020 |
| Homo sapiens | Muscleblind-like protein 1 | Potency | 2238.7 | nM | None |
| Homo sapiens | Niemann-Pick C1 protein | Potency | 1778.3 | nM | None |
| Homo sapiens | Nuclear factor erythroid 2-related factor 2 | Potency | 18356.4 | nM | None |
| Homo sapiens | Nuclear factor NF-kappa-B complex | EC50 | 1348.0 | nM | None |
| Homo sapiens | Parathyroid hormone receptor | Potency | 3981.1 | nM | None |
| Homo sapiens | Prelamin-A/C | Potency | 17.8 | nM | None |
| Homo sapiens | Rap guanine nucleotide exchange factor 3 | Potency | 100000.0 | nM | None |
| Homo sapiens | Ras-related protein Rab-9A | Potency | 1000.0 | nM | None |
| Homo sapiens | Runt-related transcription factor 1/Core-binding factor subunit beta | Potency | 3548.1 | nM | None |
| Homo sapiens | Survival motor neuron protein | Potency | 12589.3 | nM | None |
| Homo sapiens | T-24 | EC50 | 1.2 | ug.mL-1 | 10.1016/j.ejmech.2010.10.006 |
| Homo sapiens | Tyrosyl-DNA phosphodiesterase 1 | Potency | 12995.3 | nM | None |
| Homo sapiens | Tyrosyl-DNA phosphodiesterase 1 | Potency | 23109.3 | nM | None |
| Homo sapiens | Ubiquitin carboxyl-terminal hydrolase 1 | Potency | 17782.8 | nM | None |
| Human immunodeficiency virus 1 | Aberrant vpr protein | Potency | 2511.9 | nM | None |
| Influenza A virus | Nonstructural protein 1 | IC50 | 81685.0 | nM | None |
| Influenza A virus | Nonstructural protein 1 | Potency | 1584.9 | nM | None |
| Klebsiella pneumoniae | Klebsiella pneumoniae | MIC | 250.0 | ug.mL-1 | 10.1016/j.ejmech.2016.10.034 |
| Leishmania mexicana | Pyruvate kinase | Potency | 7079.5 | nM | None |
| Mus musculus | BALB/3T3 | EC50 | 0.2 | ug.mL-1 | 10.1016/j.ejmech.2010.10.006 |
| Mus musculus | BALB/3T3 | Ratio EC50 | 0.05 | None | 10.1016/j.ejmech.2010.10.006 |
| Mus musculus | BALB/3T3 | Ratio EC50 | 0.16 | None | 10.1016/j.ejmech.2010.10.006 |
| Mus musculus | Heat shock factor protein 1 | EC50 | 1260.0 | nM | None |
| Mus musculus | HT-22 | PD50 | 64.0 | nM | 10.1021/jm301485d |
| Mus musculus | HT-22 | TC50 | 7000.0 | nM | 10.1021/jm301485d |
| Mus musculus | Nuclear receptor ROR-gamma | Potency | 70.8 | nM | None |
| Mus musculus | Nuclear receptor ROR-gamma | Potency | 14125.4 | nM | None |
| Photinus pyralis | Luciferin 4-monooxygenase | Potency | 3380.8 | nM | None |
| Plasmodium falciparum | Plasmodium falciparum | IC50 | 6300.0 | nM | 10.1016/j.ejmech.2015.11.020 |
| Plasmodium falciparum | Plasmodium falciparum | Potency | 1471.6 | nM | None |
| Plasmodium falciparum | Plasmodium falciparum | Potency | 2332.3 | nM | None |
| Proteus vulgaris | Proteus vulgaris | MIC | nan | None | 10.1016/j.ejmech.2016.10.034 |
| Pseudomonas aeruginosa | Pseudomonas aeruginosa | MIC | 250.0 | ug.mL-1 | 10.1016/j.ejmech.2016.10.034 |
| Rattus norvegicus | INS1 | AC50 | 3970.0 | nM | None |
| Rattus norvegicus | Rattus norvegicus | EC50 | 239.0 | nM | 10.1016/s0960-894x(99)00411-4 |
| Rattus norvegicus | Rattus norvegicus | Emax | 98.0 | % | 10.1016/s0960-894x(99)00411-4 |
| Severe acute respiratory syndrome coronavirus 2 | Replicase polyprotein 1ab | Inhibition | nan | % | 10.1021/acs.jmedchem.2c00954 |
| Staphylococcus aureus | Staphylococcus aureus | MIC | 62.5 | ug.mL-1 | 10.1016/j.ejmech.2016.10.034 |
| Sus scrofa | Calpain 2 | IC50 | 6162.7 | nM | None |
| Trypanosoma brucei rhodesiense | Rhodesain | Inhibition | 61.0 | % | 10.1016/j.bmc.2021.116213 |
| Trypanosoma cruzi | Cruzipain | Inhibition | 48.0 | % | 10.1016/j.bmc.2021.116213 |
| Trypanosoma cruzi | Trypanosoma cruzi | IC50 | 25000.0 | nM | 10.1016/j.bmc.2014.07.030 |
| None | ADMET | TI | 109.0 | None | 10.1021/jm301485d |
| None | NON-PROTEIN TARGET | AC50 | 51510.0 | nM | None |
| None | NON-PROTEIN TARGET | AC50 | 70000.0 | nM | None |
| None | NON-PROTEIN TARGET | MIC | 250.0 | ug.mL-1 | 10.1016/j.ejmech.2016.10.034 |
| None | No relevant target | LogP | 1.55 | None | 10.1016/j.ejmech.2010.10.006 |
| None | Unchecked | AC50 | 1180.0 | nM | None |
| None | Unchecked | AC50 | 1530.0 | nM | None |
| None | Unchecked | AC50 | 1930.0 | nM | None |
| None | Unchecked | AC50 | 2370.0 | nM | None |
| None | Unchecked | AC50 | 2560.0 | nM | None |
| None | Unchecked | AC50 | 5310.0 | nM | None |
| None | Unchecked | AC50 | 5860.0 | nM | None |
| None | Unchecked | AC50 | 6210.0 | nM | None |
| None | Unchecked | AC50 | 7240.0 | nM | None |
| None | Unchecked | AC50 | 28400.0 | nM | None |
| None | Unchecked | AC50 | 70000.0 | nM | None |
| None | Unchecked | IC50 | 4200.0 | nM | 10.1016/j.bmcl.2021.128274 |
| None | Unchecked | IC50 | 11694.0 | nM | None |
| None | Unchecked | Inhibition | nan | % | 10.1016/j.ejmech.2014.06.070 |
| None | Unchecked | Potency | 891.3 | nM | None |
| None | Unchecked | Potency | 1122.0 | nM | None |
| None | Unchecked | Potency | 4256.9 | nM | None |
| None | Unchecked | Potency | 4466.8 | nM | None |
| None | Unchecked | Potency | 7079.5 | nM | None |
| None | Unchecked | Potency | 14581.0 | nM | None |
| None | Unchecked | Potency | 16360.1 | nM | None |
| None | Unchecked | Potency | 20596.2 | nM | None |
| None | Unchecked | Potency | 28183.8 | nM | None |
| None | Unchecked | Potency | 32642.7 | nM | None |
| None | Unchecked | Ratio IC50 | 15.0 | None | 10.1016/j.ejmech.2015.11.020 |