Compound Detail

CHEMBL418068

RHEIN

Enter ChEMBL ID:

Free Research Context This compound will appear in recent viewed items on the research home for this browser.

O=C(O)c1cc(O)c2c(c1)C(=O)c1cccc(O)c1C2=O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL418068
Name	RHEIN
Phase	Preclinical
Structure Type	MOL
InChI Key	FCDLCPWAQCPTKC-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

284.2

MW (Da)

1.57

ALogP

HBA

HBD

111.9

PSA (Å²)

0.62

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula	C15H8O6
MW	284.22
Aromatic Rings	2
Heavy Atoms	21
NP-Likeness	1.06

Activity Summary

IC50 53 meas. best 6.2

EC50 4 meas. best 5.29

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Acetylcholinesterase CHEMBL4078	IC50	6.2	6.2	637.0	1
Alpha-ketoglutarate-dependent dioxygenase FTO CHEMBL2331065	IC50	5.66	4.93	2180.0	4
Heat shock protein HSP90 CHEMBL2095165	IC50	5.48	5.48	3339.3	1
Unchecked CHEMBL612545	EC50	5.29	4.995	5190.0	2
Alpha-ketoglutarate-dependent dioxygenase alkB homolog 3 CHEMBL3112376	IC50	5.28	5.28	5300.0	1
Unchecked CHEMBL612545	IC50	5.25	4.8933	5680.0	3
RNA demethylase ALKBH5 CHEMBL3621037	IC50	5.05	5.025	9000.0	2
DNA oxidative demethylase ALKBH2 CHEMBL5169164	IC50	5.04	5.04	9100.0	1
Transthyretin CHEMBL3194	IC50	4.92	4.92	12000.0	1
HepG2 CHEMBL395	IC50	4.91	4.52	12300.0	2
Alpha-ketoglutarate-dependent dioxygenase AlkB CHEMBL5291506	IC50	4.9	4.9	12700.0	1
HCT-116 CHEMBL394	IC50	4.89	4.89	13000.0	1
Cholinesterase CHEMBL1914	IC50	4.77	4.77	17000.0	2
Tyrosine-protein phosphatase non-receptor type 7 CHEMBL2219	IC50	4.71	4.71	19620.0	1
Zinc finger protein mex-5 CHEMBL1293319	EC50	4.67	4.67	21569.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	4.55	4.375	28310.0	2
RNA-binding protein pos-1 CHEMBL1293304	EC50	4.54	4.54	29176.0	1
Tissue alpha-L-fucosidase CHEMBL3545	IC50	4.5	4.5	32000.0	1
Plectin CHEMBL1293240	IC50	4.49	4.49	32104.8	1
MDA-MB-231 CHEMBL400	IC50	4.38	4.38	41800.0	1
SCC-4 CHEMBL1075570	IC50	4.24	4.24	58000.0	1
SK-OV-3 CHEMBL614925	IC50	4.15	4.15	71500.0	1
A549 CHEMBL392	IC50	4.1	4.06	80000.0	2
CNE CHEMBL613824	IC50	4.09	4.09	81700.0	1
Thioredoxin reductase 1, cytoplasmic CHEMBL6035	IC50	4.08	4.08	84000.0	1
HUVEC CHEMBL613979	IC50	4.05	4.05	89740.0	1
HeLa CHEMBL399	IC50	4.04	4.04	92200.0	1
HL-60 CHEMBL383	IC50	4.0	4.0	100000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	1178.0	ng.hr.mL-1	Rattus norvegicus
AUC	1394.0	ng.hr.mL-1	Rattus norvegicus
AUC	1166.0	ng.hr.mL-1	Rattus norvegicus
AUC	1379.0	ng.hr.mL-1	Rattus norvegicus
Cmax	1023.85	nM	Rattus norvegicus
Cmax	1519.95	nM	Rattus norvegicus
MRT	4.291	hr	Rattus norvegicus
MRT	5.699	hr	Rattus norvegicus
MRT	2.918	hr	Rattus norvegicus
MRT	3.782	hr	Rattus norvegicus
T1/2	2.771	hr	Rattus norvegicus
T1/2	1.239	hr	Rattus norvegicus
Tmax	2.917	hr	Rattus norvegicus
Tmax	2.035	hr	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Acetylcholinesterase	IC50	=	637.0	nM	6.2	Inhibition Assay: AChE inhibitory activity of compounds (Ia)-(Ie) and (-)-(Ib) a...	-
Alpha-ketoglutarate-dependent dioxygenase FTO	IC50	=	2180.0	nM	5.66	Inhibition of FTO (unknown origin) demethylation activity using m6A7-Broccoli RN...	34792334
Heat shock protein HSP90	IC50	=	3339.3	nM	5.48	PUBCHEM_BIOASSAY: Tumor Hsp90 Inhibitors Dose Response Confirmation. (Class of a...	-
Unchecked	EC50	=	5190.0	nM	5.29	PUBCHEM_BIOASSAY: Fluorescent HTS Cytotoxicity/Cell viability assay (HPDE-C7K ce...	-
Alpha-ketoglutarate-dependent dioxygenase alkB homolog 3	IC50	=	5300.0	nM	5.28	Inhibition of human ALKBH3 by HPLC analysis	34792334
Unchecked	IC50	=	5680.0	nM	5.25	Inhibition of Saccharomyces cerevisiae alpha-glucosidase using maltose as substr...	31927314
RNA demethylase ALKBH5	IC50	=	9000.0	nM	5.05	Inhibition of ALKBH5 (unknown origin) expressed in Escherichia coli BL21 (DE3) u...	38805939
DNA oxidative demethylase ALKBH2	IC50	=	9100.0	nM	5.04	Inhibition of human ALKBH2 by HPLC analysis	34792334
RNA demethylase ALKBH5	IC50	=	9960.0	nM	5.0	Inhibition of ALKBH5 (unknown origin)	34792334
Transthyretin	IC50	=	12000.0	nM	4.92	Inhibition of acid-mediated aggregation of TTR V30M mutant (unknown origin) expr...	34225167
HepG2	IC50	=	12300.0	nM	4.91	Cytotoxicity against MDR1 Pgp overexpressing human HepG2 cells after 24 hrs by M...	17949858
Alpha-ketoglutarate-dependent dioxygenase AlkB	IC50	=	12700.0	nM	4.9	Inhibition of Escherichia coli AlkB by HPLC analysis	34792334
HCT-116	IC50	=	13000.0	nM	4.89	Cytotoxicity against MDR1 Pgp under-expressing human HCT116 cells after 24 hrs b...	17949858
Unchecked	IC50	=	14000.0	nM	4.85	Inhibition of Trypanosoma cruzi trans-sialidase containing catalytic domain (N58...	20097567
Cholinesterase	IC50	=	17000.0	nM	4.77	Inhibition of human serum BChE using butyrylthiocholine iodide as substrate prei...	24568372
Cholinesterase	IC50	=	17000.0	nM	4.77	Inhibition Assay: BChE inhibitory activity determinations were carried out simil...	-
Tyrosine-protein phosphatase non-receptor type 7	IC50	=	19620.0	nM	4.71	PUBCHEM_BIOASSAY: HTS Discovery of Chemical Inhibitors of HePTP, a Leukemia Targ...	-
Alpha-ketoglutarate-dependent dioxygenase FTO	IC50	=	20000.0	nM	4.7	Inhibition of FTO (unknown origin)	38805939
Unchecked	EC50	=	19800.0	nM	4.7	PUBCHEM_BIOASSAY: Fluorescent HTS Cytotoxicity/Cell viability assay (HPDE-C7 cel...	-
Alpha-ketoglutarate-dependent dioxygenase FTO	IC50	=	21000.0	nM	4.68	Displacement of ssDNA with ATTGTCA (m6A) CAGCAGA-FAM from human FTO measured aft...	34792334

Literature References

PubMed	DOI	Target Context	# Activities
22901311	10.1016/j.ejmech.2012.07.053	Rattus norvegicus	14
35963130	10.1016/j.ejmech.2022.114651	ADMET	10
23961115	10.1016/j.sjbs.2010.12.009	Helicoverpa armigera	9
23961115	10.1016/j.sjbs.2010.12.009	Spodoptera litura	9
26094120	10.1016/j.bmcl.2015.05.090	Macrophage scavenger receptor types I and II	5
-	10.6019/CHEMBL4495565	SARS-CoV-2	4
37593578	10.1039/d3md00116d	Staphylococcus epidermidis	4
31097991	10.1021/acsmedchemlett.8b00624	SMMC-7721	3
2213033	10.1021/np50069a014	NON-PROTEIN TARGET	3
-	10.1039/C6MD00252H	Bel-7402	3
11459643	10.1016/s0960-894x(01)00318-3	Estrogen receptor	3
23683594	10.1016/j.bmcl.2013.04.059	Molecular identity unknown	2
24568372	10.1021/jm401824w	Acetylcholinesterase	2
17220400	10.1128/aac.00999-06	Streptococcus mutans	2
-	10.1039/C6MD00252H	MCF7	2
27541260	10.1016/j.ejmech.2016.08.004	Unchecked	2
24568372	10.1021/jm401824w	Amyloid-beta precursor protein	2
20097567	10.1016/j.bmc.2009.12.062	Unchecked	2
-	10.1039/C6MD00252H	HepG2	2
-	10.6019/CHEMBL4495564	Replicase polyprotein 1ab	2

Data from ChEMBL 36 via Core Engine