Indigotin
AlkaPlorer ID: AK302429
Synonym: Δ2,2'-Biindoline-3,3'-dione, Δ2,2'-Bipseudoindoxyl, Diindogen, Indigo, Indigo blue, C.I. Natural Blue 1, C.I. Vat Blue 1, C.I. 75780
IUPAC Name: 2-(3-hydroxy-1H-indol-2-yl)indol-3-one
Structure
SMILES: O=C1/C(=C2\NC3=C(C=CC=C3)C2=O)NC2=CC=CC=C12
InChI: InChI=1S/C16H10N2O2/c19-15-9-5-1-3-7-11(9)17-13(15)14-16(20)10-6-2-4-8-12(10)18-14/h1-8,17-18H/b14-13+
InChIKey: COHYTHOBJLSHDF-BUHFOSPRSA-N
Source
Properties Information
Molecule Weight: 262.26800000000003
TPSA？: 58.2
MolLogP？: 2.8148
Number of H-Donors: 2
Number of H-Acceptors: 4
RingCount: 4
Activities Information
| Organism | Target Name | Standard Type | Standard Value | Standard Units | doi |
|---|---|---|---|---|---|
| Escherichia coli K-12 | Beta-lactamase AmpC | Change in IC50 | 50.0 | fold | 10.1021/jm020427b |
| Homo sapiens | A549 | Activity | nan | None | 10.1021/np3002833 |
| Homo sapiens | Aldehyde dehydrogenase 1A1 | Potency | 3162.3 | nM | None |
| Homo sapiens | Aryl hydrocarbon receptor | EC50 | 5.0 | nM | 10.1016/j.ejmech.2022.114845 |
| Homo sapiens | Aryl hydrocarbon receptor | EC50 | 1700.0 | nM | 10.1016/j.bmc.2009.12.036 |
| Homo sapiens | Bel-7402 | Activity | nan | None | 10.1021/np3002833 |
| Homo sapiens | Beta-chymotrypsin | IC50 | 90000.0 | nM | 10.1021/jm020427b |
| Homo sapiens | BGC-823 | Activity | nan | None | 10.1021/np3002833 |
| Homo sapiens | Cyclin-dependent kinase 1/cyclin B | IC50 | 100000.0 | nM | 10.1021/jm030561b |
| Homo sapiens | Cyclin-dependent kinase 2 | IC50 | 70000.0 | nM | 10.1021/jm020427b |
| Homo sapiens | Cyclin-dependent kinase 2/cyclin E1 | IC50 | 1000.0 | nM | 10.1016/j.ejmech.2015.11.047 |
| Homo sapiens | Cyclin-dependent kinase 5/CDK5 activator 1 | IC50 | 100000.0 | nM | 10.1021/jm030561b |
| Homo sapiens | DNA-(apurinic or apyrimidinic site) lyase | Potency | 7943.3 | nM | None |
| Homo sapiens | Glycogen synthase kinase-3 | IC50 | 100000.0 | nM | 10.1021/jm030561b |
| Homo sapiens | HCT-8 | Activity | nan | None | 10.1021/np3002833 |
| Homo sapiens | Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 | Potency | 5011.9 | nM | None |
| Homo sapiens | KETR3 | Activity | nan | None | 10.1021/np3002833 |
| Homo sapiens | MCF7 | Activity | nan | None | 10.1021/np3002833 |
| Homo sapiens | Tyrosine-protein kinase SRC | IC50 | 28000.0 | nM | 10.1021/jm020427b |
| Homo sapiens | Tyrosyl-DNA phosphodiesterase 1 | Potency | 3548.1 | nM | None |
| Homo sapiens | Tyrosyl-DNA phosphodiesterase 1 | Potency | 39810.7 | nM | None |
| Homo sapiens | Ubiquitin carboxyl-terminal hydrolase 1 | Potency | 63095.7 | nM | None |
| Human alphaherpesvirus 1 | Human alphaherpesvirus 1 | Activity | nan | None | 10.1021/np3002833 |
| Human immunodeficiency virus 1 | Human immunodeficiency virus 1 | Activity | nan | None | 10.1021/np3002833 |
| Mycobacterium tuberculosis | Mycobacterium tuberculosis | MIC | 32000.0 | nM | 10.1016/j.bmcl.2013.11.024 |
| Photinus pyralis | Luciferin 4-monooxygenase | Potency | 12817.8 | nM | None |
| Plasmodium falciparum | Plasmodium falciparum | Potency | 9528.3 | nM | None |
| Rattus norvegicus | Inositol monophosphatase 1 | Potency | 3162.3 | nM | None |
| Thermus thermophilus | Malate dehydrogenase | IC50 | 60000.0 | nM | 10.1021/jm020427b |
| Trypanosoma brucei | 6-phospho-1-fructokinase | Potency | 7943.3 | nM | None |
| None | Unchecked | Ac50 | 15.85 | uM | None |
| None | Unchecked | Ac50 | 25.12 | uM | None |
| None | Unchecked | AC50 | 15848.9 | nM | None |
| None | Unchecked | AC50 | 25118.9 | nM | None |
| None | Unchecked | IC50 | 30000.0 | nM | 10.1021/jm020427b |
| None | Unchecked | IC50 | 200000.0 | nM | 10.1016/S0960-894X(00)80378-9 |
| None | Unchecked | Potency | 22387.2 | nM | None |