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Compound Detail

CHEMBL446452

ARUNDINE
🧪 Phase III
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🧪 Phase III
c1ccc2c(Cc3c[nH]c4ccccc34)c[nH]c2c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL446452
Name ARUNDINE
Phase Phase III
Structure Type MOL
InChI Key VFTRKSBEFQDZKX-UHFFFAOYSA-N

Known Names

1,1-bis(3'-indolyl)methane 3,3'-diindolylmethane 3,3-diindolylmethane Arundine Diindolylmethane
9
Targets
37
Activities
3
Assay Types
0
PK Parameters
20
Publications
5
Known Names
3
Indications

Molecular Properties

246.3
MW (Da)
4.24
ALogP
0
HBA
2
HBD
31.6
PSA (Ų)
0.53
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral

Flags

Natural Product

Extended Properties

Molecular Formula C17H14N2
MW 246.31
Aromatic Rings 4
Heavy Atoms 19
NP-Likeness -0.01

Indications

Uterine Cervical Neoplasms Breast Neoplasms Prostatic Neoplasms

Activity Summary

EC50 20 meas. best 6.6
Kd 10 meas. best 8.01
IC50 7 meas. best 5.9

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 Kd 8.01 6.575 9.7 4
Aryl hydrocarbon receptor
CHEMBL3201
 Kd 7.05 7.05 90.0 1
Aryl hydrocarbon receptor
CHEMBL6099
 Kd 7.05 7.05 90.0 1
G-protein coupled receptor 84
CHEMBL3714079
 EC50 6.6 5.7457 252.0 14
Leishmania donovani
CHEMBL367
 IC50 5.9 5.9 1250.0 1
G-protein coupled receptor 84
CHEMBL4523386
 EC50 5.37 5.37 4270.0 1
MCF7
CHEMBL387
 IC50 5.26 4.78 5500.0 2
MDA-MB-231
CHEMBL400
 IC50 5.0 5.0 10000.0 1
Aryl hydrocarbon receptor
CHEMBL3201
 EC50 4.11 4.11 78000.0 1
Aryl hydrocarbon receptor
CHEMBL6099
 EC50 4.11 4.11 78000.0 1
Unchecked
CHEMBL612545
 EC50 3.64 3.5 230000.0 2
U-251
CHEMBL615022
 EC50 3.55 3.55 280000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Kd = 9.7 nM 8.01 Binding affinity to recombinant wild type Leishmania donovani AG83 topoisomerase... 19332675
Unchecked Kd = 50.0 nM 7.3 Binding affinity to Leishmania donovani small subunit of topoisomerase 1b 19332675
Aryl hydrocarbon receptor Kd = 90.0 nM 7.05 Displacement of 2-azido-3-[125I]7,8-dibromodibenzo-pdioxin from C57BL/6J mouse l... 31727470
Aryl hydrocarbon receptor Kd = 90.0 nM 7.05 Binding affinity to AhR (unknown origin) assessed as dissociation constant 36274276
G-protein coupled receptor 84 EC50 = 252.0 nM 6.6 Agonist activity at Gi coupled human GPR84 expressed in CHO cells assessed as in... 28406627
G-protein coupled receptor 84 EC50 = 368.0 nM 6.43 Positive allosteric modulation of recombinant human GPR84 expressed in CHO cell ... 31721581
Unchecked Kd = 428.0 nM 6.37 Binding affinity to Leishmania donovani large subunit of topoisomerase 1b 19332675
G-protein coupled receptor 84 EC50 = 500.0 nM 6.3 Agonist activity at human N-terminal FLAG-tagged GPR84 receptor stably expressed... 31721581
G-protein coupled receptor 84 EC50 = 700.0 nM 6.16 Agonist activity at human N-terminal FLAG-tagged GPR84 receptor stably expressed... 31721581
G-protein coupled receptor 84 EC50 = 1000.0 nM 6.0 Agonist activity at recombinant human N-terminal epitope tagged/C-terminal eYFP-... 31721581
G-protein coupled receptor 84 EC50 = 1110.0 nM 5.96 Agonist activity at recombinant human HA-tagged GPR84 stably expressed in HEK293... 31721581
G-protein coupled receptor 84 EC50 = 1260.0 nM 5.9 Agonist activity at recombinant human N-terminal epitope tagged/C-terminal eYFP-... 31721581
Leishmania donovani IC50 = 1250.0 nM 5.9 Antimicrobial activity against wild type Leishmania donovani AG83 assessed as in... 19332675
G-protein coupled receptor 84 EC50 = 1640.0 nM 5.79 Agonist activity at human GPR84 expressed in CHO cells assessed as beta-arrestin... 28406627
G-protein coupled receptor 84 EC50 = 2880.0 nM 5.54 Positive allosteric modulation of Gi coupled human GPR84 expressed in CHO cells ... 28406627
G-protein coupled receptor 84 EC50 = 4270.0 nM 5.37 Agonist activity at mouse Galphai2-coupled GPR84 expressed in human Flp-In-T-REx... 33267584
G-protein coupled receptor 84 EC50 = 5120.0 nM 5.29 Positive allosteric modulation of Gi coupled human GPR84 expressed in CHO cells ... 28406627
MCF7 IC50 = 5500.0 nM 5.26 Antitumor activity against MCF7 cells 17602463
G-protein coupled receptor 84 EC50 = 5900.0 nM 5.23 Agonist activity at human Gi1alpha-coupled GPR84 expressed in baculovirus infect... 31721581
G-protein coupled receptor 84 EC50 = 6280.0 nM 5.2 Positive allosteric modulation of Gi coupled human GPR84 expressed in CHO cells ... 28406627

Literature References

PubMed DOI Target Context # Activities
19332675 10.1128/aac.01648-08 Unchecked 17
19332675 10.1128/aac.01648-08 Leishmania donovani 13
17583501 10.1016/j.bmcl.2007.06.025 Oryza sativa 12
28406627 10.1021/acs.jmedchem.6b01593 G-protein coupled receptor 84 12
31721581 10.1021/acs.jmedchem.9b01339 G-protein coupled receptor 84 11
28406627 10.1021/acs.jmedchem.6b01593 No relevant target 6
19332675 10.1128/aac.01648-08 DNA topoisomerase I 5
28256372 10.1016/j.bmcl.2017.02.033 Unchecked 4
37154394 10.1021/acs.jmedchem.3c00287 Unchecked 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
19332675 10.1128/aac.01648-08 DNA topoisomerase type IB small subunit 4
37154394 10.1021/acs.jmedchem.3c00287 Mus musculus 3
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
31727470 10.1016/j.ejmech.2019.111842 Aryl hydrocarbon receptor 2
36274276 10.1016/j.ejmech.2022.114845 Aryl hydrocarbon receptor 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
19540023 10.1016/j.ejmech.2009.05.011 NON-PROTEIN TARGET 2
28406627 10.1021/acs.jmedchem.6b01593 Free fatty acid receptor 4 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
- 10.1007/s00044-013-0737-7 NON-PROTEIN TARGET 2

Data from ChEMBL 36 via Core Engine