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Indirubin

AlkaPlorer ID: AK319833

Synonym: None

IUPAC Name: 2-(2-hydroxy-1H-indol-3-yl)indol-3-one

Structure

SMILES: O=C1/C(=C2/C(O)=NC3=CC=CC=C23)NC2=CC=CC=C12

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InChI: InChI=1S/C16H10N2O2/c19-15-10-6-2-4-8-12(10)17-14(15)13-9-5-1-3-7-11(9)18-16(13)20/h1-8,17H,(H,18,20)/b14-13-

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InChIKey: CRDNMYFJWFXOCH-YPKPFQOOSA-N

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Properties Information

Molecule Weight: 262.26800000000003

TPSA？: 61.69

MolLogP？: 3.3077000000000014

Number of H-Donors: 2

Number of H-Acceptors: 3

RingCount: 4

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Chlamydia pneumoniae Chlamydia pneumoniae Inhibition 2.0 % 10.1021/acs.jnatprod.6b01052
Danio rerio Danio rerio IC50 100.0 nM None
Electrophorus electricus Acetylcholinesterase Inhibition 7.97 % 10.1016/j.bmc.2012.09.040
Equus caballus Cholinesterase Inhibition 13.7 % 10.1016/j.bmc.2012.09.040
Escherichia coli K-12 Beta-lactamase AmpC Change in IC50 4.0 fold 10.1021/jm020427b
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 A549 IC50 10000.0 nM 10.1021/acs.jmedchem.1c01311
Homo sapiens A549 IC50 31000.0 nM 10.1016/j.bmcl.2005.05.105
Homo sapiens A549 IC50 100000.0 nM 10.1016/j.bmcl.2016.02.015
Homo sapiens Aryl hydrocarbon receptor EC50 0.2 nM 10.1016/j.ejmech.2022.114845
Homo sapiens Bel-7402 Activity nan None 10.1021/np3002833
Homo sapiens Beta-chymotrypsin IC50 100000.0 nM 10.1021/jm020427b
Homo sapiens BGC-823 Activity nan None 10.1021/np3002833
Homo sapiens CDK2/Cyclin A2 IC50 2200.0 nM 10.1016/j.ejmech.2021.113652
Homo sapiens CDK2/Cyclin A2 IC50 2200.0 nM 10.1021/acs.jmedchem.1c02064
Homo sapiens CDK2/Cyclin A2 IC50 2200.0 nM 10.1021/acs.jmedchem.7b00324
Homo sapiens CDK2/Cyclin A2 IC50 7500.0 nM 10.1021/acs.jmedchem.7b00324
Homo sapiens CDK2/Cyclin A2 Inhibition 8.5 % 10.1021/acs.jmedchem.1c01311
Homo sapiens CDK4/Cyclin D3 Inhibition 1.0 % 10.1021/acs.jmedchem.1c01311
Homo sapiens CDK6/cyclin D3 IC50 nan None 10.1021/acs.jmedchem.7b00324
Homo sapiens CDK6/cyclin D3 Inhibition 25.1 % 10.1021/acs.jmedchem.1c01311
Homo sapiens Cyclin-dependent kinase IC50 2200.0 nM 10.1021/acs.jnatprod.7b00390
Homo sapiens Cyclin-dependent kinase 1 IC50 10000.0 nM 10.1016/j.ejmech.2010.08.004
Homo sapiens Cyclin-dependent kinase 1/cyclin B IC50 6500.0 nM 10.1021/jm030561b
Homo sapiens Cyclin-dependent kinase 1/cyclin B IC50 10000.0 nM 10.1021/jm031016d
Homo sapiens Cyclin-dependent kinase 1/cyclin B1 IC50 10000.0 nM 10.1021/acs.jmedchem.7b00324
Homo sapiens Cyclin-dependent kinase 1/cyclin B1 IC50 20000.0 nM 10.1021/acs.jmedchem.7b00324
Homo sapiens Cyclin-dependent kinase 2 IC50 2200.0 nM 10.1021/acs.jmedchem.8b01469
Homo sapiens Cyclin-dependent kinase 2 IC50 2200.0 nM 10.1021/jm020427b
Homo sapiens Cyclin-dependent kinase 2/cyclin E1 IC50 2200.0 nM 10.1021/acs.jmedchem.7b00324
Homo sapiens Cyclin-dependent kinase 2/cyclin E1 IC50 7500.0 nM 10.1021/acs.jmedchem.7b00324
Homo sapiens Cyclin-dependent kinase 4/cyclin D1 IC50 12000.0 nM 10.1016/j.ejmech.2021.113652
Homo sapiens Cyclin-dependent kinase 4/cyclin D1 IC50 12000.0 nM 10.1021/acs.jmedchem.1c02064
Homo sapiens Cyclin-dependent kinase 4/cyclin D1 IC50 12000.0 nM 10.1021/acs.jmedchem.7b00324
Homo sapiens Cyclin-dependent kinase 5/CDK5 activator 1 IC50 5000.0 nM 10.1021/jm030561b
Homo sapiens Cyclin-dependent kinase 5/CDK5 activator 1 IC50 5500.0 nM 10.1016/j.ejmech.2021.113652
Homo sapiens Cyclin-dependent kinase 5/CDK5 activator 1 IC50 5500.0 nM 10.1021/acs.jmedchem.7b00324
Homo sapiens Cyclin-dependent kinase 5/CDK5 activator 1 IC50 10000.0 nM 10.1016/j.ejmech.2021.113652
Homo sapiens Cyclin-dependent kinase 5/CDK5 activator 1 IC50 10000.0 nM 10.1021/jm031016d
Homo sapiens Cyclin-dependent kinase 5/CDK5 activator 1 IC50 10000.0 nM 10.1021/jm060314i
Homo sapiens DNA polymerase iota Potency 100000.0 nM None
Homo sapiens DU-145 IC50 6800.0 nM 10.1016/j.bmcl.2010.05.039
Homo sapiens Geminin Potency 125.9 nM None
Homo sapiens Glycogen synthase kinase-3 IC50 1000.0 nM 10.1021/jm031016d
Homo sapiens Glycogen synthase kinase-3 IC50 1000.0 nM 10.1021/jm060314i
Homo sapiens Glycogen synthase kinase-3 IC50 2500.0 nM 10.1021/jm030561b
Homo sapiens Glycogen synthase kinase-3 beta IC50 4.0 nM 10.1016/j.ejmech.2015.10.018
Homo sapiens Glycogen synthase kinase-3 beta IC50 5.0 nM 10.1016/j.ejmech.2016.09.058
Homo sapiens Glycogen synthase kinase-3 beta IC50 600.0 nM 10.1021/acs.jmedchem.7b00324
Homo sapiens H4 Activity 35.1 % 10.1073/pnas.0709695104
Homo sapiens H4 Activity 59.18 % 10.1073/pnas.0709695104
Homo sapiens H4 Activity 73.16 % 10.1073/pnas.0709695104
Homo sapiens H4 Activity 94.5 % 10.1073/pnas.0709695104
Homo sapiens H4 Activity 95.3 % 10.1073/pnas.0709695104
Homo sapiens H4 Activity 100.5 % 10.1073/pnas.0709695104
Homo sapiens H4 Activity 101.26 % 10.1073/pnas.0709695104
Homo sapiens H4 Activity 105.91 % 10.1073/pnas.0709695104
Homo sapiens H4 Activity 149.7 % 10.1073/pnas.0709695104
Homo sapiens H4 Activity 158.69 % 10.1073/pnas.0709695104
Homo sapiens H4 Activity 172.28 % 10.1073/pnas.0709695104
Homo sapiens HCT-8 Activity nan None 10.1021/np3002833
Homo sapiens HeLa IC50 10000.0 nM 10.1021/acs.jmedchem.1c01311
Homo sapiens HeLa IC50 40000.0 nM 10.1016/j.ejmech.2021.113652
Homo sapiens HepG2 IC50 10000.0 nM 10.1021/acs.jmedchem.1c01311
Homo sapiens HepG2 IC50 100000.0 nM 10.1016/j.bmc.2017.07.009
Homo sapiens HepG2 IC50 nan None 10.1016/j.bmcl.2015.02.053
Homo sapiens Histone deacetylase Inhibition 17.2 % 10.1021/acs.jmedchem.1c01311
Homo sapiens HL Activity 92.5 % 10.1021/acs.jnatprod.6b01052
Homo sapiens HL-60 IC50 100000.0 nM 10.1016/j.bmcl.2005.05.105
Homo sapiens HL-60 LC50 98.1 ug.mL-1 10.1016/j.ejmech.2021.113652
Homo sapiens HT-1080 IC50 42200.0 nM 10.1016/j.bmcl.2005.05.105
Homo sapiens HUVEC Activity nan None 10.1016/j.bmcl.2011.07.011
Homo sapiens Importin subunit beta-1/Snurportin-1 Potency 89125.1 nM None
Homo sapiens IMR-32 Activity nan None 10.1016/j.bmcl.2011.07.011
Homo sapiens Insulin-like growth factor I receptor IC50 1000000.0 nM 10.1021/acs.jmedchem.7b00324
Homo sapiens K562 IC50 10000.0 nM 10.1021/acs.jmedchem.1c01311
Homo sapiens K562 IC50 100000.0 nM 10.1016/j.bmcl.2018.04.019
Homo sapiens K562/VCR IC50 100000.0 nM 10.1016/j.bmcl.2018.04.019
Homo sapiens KCL-22 Activity nan None 10.1021/acs.jnatprod.6b00285
Homo sapiens KETR3 Activity nan None 10.1021/np3002833
Homo sapiens LoVo IC50 2200.0 nM 10.1016/j.bmcl.2010.05.039
Homo sapiens LoVo IC50 100000.0 nM 10.1016/j.bmcl.2016.02.015
Homo sapiens MAP kinase ERK2 Potency 31622.8 nM None
Homo sapiens MCF7 Activity nan None 10.1021/np3002833
Homo sapiens MCF7 IC50 4000.0 nM 10.1016/j.bmc.2013.11.031
Homo sapiens MCF7 IC50 6700.0 nM 10.1016/j.bmcl.2010.05.039
Homo sapiens MCF7 IC50 9910.0 nM 10.1021/acs.jmedchem.7b00324
Homo sapiens MCF7 IC50 10000.0 nM 10.1021/acs.jmedchem.1c01311
Homo sapiens MCF7 IC50 100000.0 nM 10.1016/j.bmcl.2016.02.015
Homo sapiens Menin/Histone-lysine N-methyltransferase MLL Potency 1122.0 nM None
Homo sapiens Microtubule-associated protein tau Potency 89.1 nM None
Homo sapiens Microtubule-associated protein tau Potency 100.0 nM None
Homo sapiens Microtubule-associated protein tau Potency 141.3 nM None
Homo sapiens Microtubule-associated protein tau Potency 199.5 nM None
Homo sapiens Microtubule-associated protein tau Potency 251.2 nM None
Homo sapiens Microtubule-associated protein tau Potency 398.1 nM None
Homo sapiens MV4-11 IC50 10000.0 nM 10.1016/j.bmcl.2010.01.039
Homo sapiens NHDF Activity nan None 10.1016/j.bmcl.2011.07.011
Homo sapiens PC-3 Activity 77.1 % 10.1016/j.ejmech.2021.113652
Homo sapiens PC-3 Activity 91.3 % 10.1016/j.ejmech.2021.113652
Homo sapiens Protein-glutamine gamma-glutamyltransferase IC50 100000.0 nM 10.1016/j.bmcl.2010.12.037
Homo sapiens Ras-related protein Rab-9A Potency 5623.4 nM None
Homo sapiens Regulator of G-protein signaling 4 Potency 50118.7 nM None
Homo sapiens Serine/threonine-protein kinase 17B IC50 10000.0 nM 10.1016/j.bmcl.2016.03.111
Homo sapiens SH-SY5Y Survival 104.0 % 10.1021/jm060314i
Homo sapiens SK-MEL-28 IC50 100000.0 nM 10.1016/j.bmcl.2016.02.015
Homo sapiens SK-N-SH Activity nan None 10.1016/j.bmcl.2011.07.011
Homo sapiens Survival motor neuron protein Potency 19952.6 nM None
Homo sapiens Tyrosine-protein kinase receptor FLT3 IC50 10000.0 nM 10.1016/j.bmcl.2010.01.039
Homo sapiens Tyrosine-protein kinase SRC IC50 18000.0 nM 10.1021/jm020427b
Homo sapiens U-118-MG IC50 12500.0 nM 10.1016/j.ejmech.2021.113652
Homo sapiens U2OS Activity 38.0 % 10.1016/j.ejmech.2021.113652
Homo sapiens U2OS Activity 40.0 % 10.1016/j.ejmech.2021.113652
Homo sapiens U-87 MG IC50 12500.0 nM 10.1016/j.ejmech.2021.113652
Homo sapiens Vitamin D receptor Potency 39810.7 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
Leishmania mexicana Pyruvate kinase Potency 17782.8 nM None
Mus musculus HT-22 Activity nan None 10.1016/j.bmcl.2017.10.069
Mus musculus RAW264.7 IC50 6100.0 nM 10.1016/j.bmcl.2010.05.039
Mycobacterium tuberculosis Mycobacterium tuberculosis MIC 32000.0 nM 10.1016/j.bmcl.2013.11.024
Plasmodium falciparum Plasmodium falciparum IC50 1100.0 nM 10.1016/j.bmcl.2010.05.039
Rattus norvegicus Inositol monophosphatase 1 Potency 3548.1 nM None
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition -1.301 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition -0.12 % 10.6019/CHEMBL4495565
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 2.15 % 10.21203/rs.3.rs-23951/v1
Sus scrofa Glycogen synthase kinase-3 IC50 1000.0 nM 10.1016/j.ejmech.2021.113652
Thermus thermophilus Malate dehydrogenase IC50 30000.0 nM 10.1021/jm020427b
Toxoplasma gondii Toxoplasma gondii ID50 500.0 uM 10.1128/aac.00903-08
None ADMET TD50 500.0 uM 10.1128/aac.00903-08
None ADMET TI nan None 10.1128/aac.00903-08
None Molecular identity unknown FC 2.04 None 10.1016/j.bmcl.2009.02.083
None NON-PROTEIN TARGET Activity nan None 10.1016/j.bmcl.2011.07.011
None NON-PROTEIN TARGET IC50 200.0 nM 10.1016/j.bmcl.2016.02.015
None NON-PROTEIN TARGET IC50 6900.0 nM 10.1016/j.bmcl.2010.05.039
None NON-PROTEIN TARGET IC50 9900.0 nM 10.1016/j.bmc.2013.11.031
None NON-PROTEIN TARGET IC50 10000.0 nM 10.1016/j.bmc.2010.04.066
None NON-PROTEIN TARGET IC50 10000.0 nM 10.1016/j.bmcl.2010.01.039
None NON-PROTEIN TARGET IC50 30500.0 nM 10.1016/j.bmcl.2016.02.015
None NON-PROTEIN TARGET IC50 100000.0 nM 10.1016/j.bmcl.2016.02.015
None No relevant target Solubility 1.0 ug.mL-1 10.1016/j.bmc.2011.03.069
None Unchecked IC50 7500.0 nM 10.1016/j.ejmech.2021.113652
None Unchecked IC50 10000.0 nM 10.1016/j.ejmech.2021.113652
None Unchecked IC50 10000.0 nM 10.1021/acs.jmedchem.1c02064
None Unchecked IC50 10000.0 nM 10.1021/jm060314i
None Unchecked IC50 20000.0 nM 10.1021/jm020427b
None Unchecked IC50 100000.0 nM 10.1016/j.bmcl.2005.05.105
None Unchecked INH 2.0 uM 10.1016/j.bmc.2010.04.066
None Unchecked Potency 501.2 nM None

Metabolism Information