Compound Detail

CHEMBL1276127

INDIRUBIN

🧪 Phase II

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🧪 Phase II

O=C1Nc2ccccc2/C1=C1/Nc2ccccc2C1=O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL1276127
Name	INDIRUBIN
Phase	Phase II
Structure Type	MOL
InChI Key	CRDNMYFJWFXOCH-YPKPFQOOSA-N

Known Names

C.I. 75790 Couroupitine b Indirubin NSC-105327

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

262.3

MW (Da)

2.66

ALogP

HBA

HBD

58.2

PSA (Å²)

0.72

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Achiral

Flags

Natural Product

Extended Properties

Molecular Formula	C16H10N2O2
MW	262.27
Aromatic Rings	2
Heavy Atoms	20
NP-Likeness	0.47

Indications

Psoriasis Psoriasis

Activity Summary

IC50 57 meas. best 8.4

EC50 1 meas. best 9.7

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Aryl hydrocarbon receptor CHEMBL3201	EC50	9.7	9.7	0.2	1
Glycogen synthase kinase-3 beta CHEMBL262	IC50	8.4	7.64	4.0	3
NON-PROTEIN TARGET CHEMBL3879801	IC50	6.7	5.276	200.0	5
Glycogen synthase kinase-3 CHEMBL2095188	IC50	6.0	5.8667	1000.0	3
Glycogen synthase kinase-3 CHEMBL2366565	IC50	6.0	6.0	1000.0	1
Plasmodium falciparum CHEMBL364	IC50	5.96	5.96	1100.0	1
Cyclin-dependent kinase CHEMBL3559691	IC50	5.66	5.66	2200.0	1
LoVo CHEMBL614721	IC50	5.66	5.66	2200.0	1
CDK2/Cyclin A2 CHEMBL3038469	IC50	5.66	5.525	2200.0	4
Cyclin-dependent kinase 2 CHEMBL301	IC50	5.66	5.66	2200.0	2
Cyclin-dependent kinase 2/cyclin E1 CHEMBL1907605	IC50	5.66	5.39	2200.0	2
MCF7 CHEMBL387	IC50	5.4	5.19	4000.0	3
Cyclin-dependent kinase 5/CDK5 activator 1 CHEMBL1907600	IC50	5.3	5.1367	5000.0	6
RAW264.7 CHEMBL612557	IC50	5.21	5.21	6100.0	1
Cyclin-dependent kinase 1/cyclin B CHEMBL2094127	IC50	5.19	5.095	6500.0	2
DU-145 CHEMBL613508	IC50	5.17	5.17	6800.0	1
Unchecked CHEMBL612545	IC50	5.12	4.964	7500.0	5
Cyclin-dependent kinase 1/cyclin B1 CHEMBL1907602	IC50	5.0	4.85	10000.0	2
Cyclin-dependent kinase 1 CHEMBL308	IC50	5.0	5.0	10000.0	1
Cyclin-dependent kinase 4/cyclin D1 CHEMBL1907601	IC50	4.92	4.92	12000.0	3
U-118-MG CHEMBL1075602	IC50	4.9	4.9	12500.0	1
U-87 MG CHEMBL614247	IC50	4.9	4.9	12500.0	1
Proto-oncogene tyrosine-protein kinase Src CHEMBL267	IC50	4.75	4.75	18000.0	1
HCT-116 CHEMBL394	IC50	4.71	4.71	19520.0	1
Malate dehydrogenase CHEMBL4255	IC50	4.52	4.52	30000.0	1
A549 CHEMBL392	IC50	4.51	4.51	31000.0	1
HeLa CHEMBL399	IC50	4.4	4.4	40000.0	2
HT-1080 CHEMBL614580	IC50	4.38	4.38	42200.0	1
Chymotrypsinogen B CHEMBL4796	IC50	4.0	4.0	100000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	70.19	mL.min-1.kg-1	Homo sapiens
CL	15.99	mL.min-1.kg-1	Homo sapiens
T1/2	0.3807	hr	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Aryl hydrocarbon receptor	EC50	=	0.2	nM	9.7	Activation of human AhR expressed in Saccharomyces cerevisiae YCM3 coexpressing ...	36274276
Glycogen synthase kinase-3 beta	IC50	=	4.0	nM	8.4	Competitive inhibition of glycogen synthase kinase-3 beta (unknown origin) using...	26562543
Glycogen synthase kinase-3 beta	IC50	=	5.0	nM	8.3	Inhibition of GSK3beta (unknown origin) expressed in sf9 cells using GS-1 as sub...	27689729
NON-PROTEIN TARGET	IC50	=	200.0	nM	6.7	Antiproliferative activity against apoptosis sensitive mouse B16F10 cells after ...	26883150
Glycogen synthase kinase-3 beta	IC50	=	600.0	nM	6.22	Inhibition of recombinant GSK3beta (unknown origin) after 10 mins in presence of...	28557430
Glycogen synthase kinase-3	IC50	=	1000.0	nM	6.0	Inhibitory activity against GSK-3-alpha/beta from porcine brain	14761195
Glycogen synthase kinase-3	IC50	=	1000.0	nM	6.0	Inhibition of porcine brain GSK3alpha/beta	16854069
Glycogen synthase kinase-3	IC50	=	1000.0	nM	6.0	Inhibition of porcine brain GSK-3alpha/beta incubated for 30 mins in presence of...	34161865
Plasmodium falciparum	IC50	=	1100.0	nM	5.96	Antimalarial activity against chloroquine-resistant Plasmodium falciparum W2 ass...	20627564
Cyclin-dependent kinase 2	IC50	=	2200.0	nM	5.66	Inhibition of CDK2 (unknown origin)	30543440
LoVo	IC50	=	2200.0	nM	5.66	Cytotoxicity against human LoVo cells after 24 hrs by MTT assay	20627564
Cyclin-dependent kinase 2	IC50	=	2200.0	nM	5.66	Inhibition of Cyclin-dependent kinase 2 (CDK2)	12672248
Cyclin-dependent kinase 2/cyclin E1	IC50	=	2200.0	nM	5.66	Inhibition of CDK2/CyclinE (unknown origin)	28557430
CDK2/Cyclin A2	IC50	=	2200.0	nM	5.66	Inhibition of full length human C-terminal His6-tagged CDK2/N-terminal GST-tagge...	28557430
Cyclin-dependent kinase	IC50	=	2200.0	nM	5.66	Inhibition of recombinant human CDK expressed in baculovirus infected sf9 cells ...	28722414
CDK2/Cyclin A2	IC50	=	2200.0	nM	5.66	Inhibition of CDK2/Cyclin A (unknown origin)	35485642
CDK2/Cyclin A2	IC50	=	2200.0	nM	5.66	Inhibition of CDK2/cyclin A (unknown origin)	34161865
Glycogen synthase kinase-3	IC50	=	2500.0	nM	5.6	Inhibition of porcine GSK-3-alpha/beta kinase	15163202
MCF7	IC50	=	4000.0	nM	5.4	Antiproliferative activity against human MCF7 cells after 3 days by SRB assay	24326279
Cyclin-dependent kinase 5/CDK5 activator 1	IC50	=	5000.0	nM	5.3	Inhibition of Cyclin-dependent kinase 5-p35nck5a	15163202

Literature References

PubMed	DOI	Target Context	# Activities
18024584	10.1073/pnas.0709695104	H4	11
26883150	10.1016/j.bmcl.2016.02.015	NON-PROTEIN TARGET	5
-	10.6019/CHEMBL4495565	SARS-CoV-2	4
37801824	10.1016/j.ejmech.2023.115829	ADMET	3
34161865	10.1016/j.ejmech.2021.113652	U2OS	2
28557430	10.1021/acs.jmedchem.7b00324	Cyclin-dependent kinase 2/cyclin E1	2
18824607	10.1128/aac.00903-08	ADMET	2
34161865	10.1016/j.ejmech.2021.113652	Unchecked	2
-	10.6019/CHEMBL4651402	SARS-CoV-2	2
28557430	10.1021/acs.jmedchem.7b00324	Cyclin-dependent kinase 1/cyclin B1	2
29122482	10.1016/j.bmcl.2017.10.069	HT-22	2
-	10.6019/CHEMBL4495564	Replicase polyprotein 1ab	2
34161865	10.1016/j.ejmech.2021.113652	PC-3	2
12672248	10.1021/jm020427b	Beta-lactamase	2
28557430	10.1021/acs.jmedchem.7b00324	CDK2/Cyclin A2	2
-	10.6019/CHEMBL4808148	Histone deacetylase 6	2
34161865	10.1016/j.ejmech.2021.113652	Cyclin-dependent kinase 5/CDK5 activator 1	2
27726390	10.1021/acs.jnatprod.6b00285	KCL-22	2
15993584	10.1016/j.bmcl.2005.05.105	A549	1
12672248	10.1021/jm020427b	Malate dehydrogenase	1

Data from ChEMBL 36 via Core Engine