Compound Detail

CHEMBL128000

BUTEIN

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O=C(/C=C/c1ccc(O)c(O)c1)c1ccc(O)cc1O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL128000
Name	BUTEIN
Phase	Preclinical
Structure Type	MOL
InChI Key	AYMYWHCQALZEGT-ORCRQEGFSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

272.3

MW (Da)

2.41

ALogP

HBA

HBD

98.0

PSA (Å²)

0.39

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	C15H12O5
MW	272.26
Aromatic Rings	2
Heavy Atoms	20
NP-Likeness	0.96

Activity Summary

IC50 32 meas. best 8.34

Ki 3 meas. best 7.85

Kd 1 meas. best 4.0

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Cyclooxygenase CHEMBL2095157	IC50	8.34	8.34	4.6	1
Polyunsaturated fatty acid 5-lipoxygenase CHEMBL312	IC50	8.34	8.34	4.6	2
Enoyl-acyl-carrier protein reductase CHEMBL4150	Ki	7.85	6.2133	14.0	3
Aldo-keto reductase family 1 member B1 CHEMBL2622	IC50	6.35	6.35	450.0	1
Angiotensin-converting enzyme CHEMBL4074	IC50	6.14	6.14	730.0	1
Xanthine dehydrogenase/oxidase CHEMBL3649	IC50	5.89	5.89	1300.0	1
Histone deacetylase 6 CHEMBL1865	IC50	5.67	5.67	2146.0	1
BV-2 CHEMBL614781	IC50	5.37	5.0967	4300.0	3
RAW264.7 CHEMBL612557	IC50	5.28	5.28	5300.0	1
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform CHEMBL4005	IC50	5.19	5.19	6400.0	1
17-beta-hydroxysteroid dehydrogenase type 2 CHEMBL2789	IC50	5.14	5.14	7300.0	1
Epidermal growth factor receptor CHEMBL203	IC50	5.1	4.95	8000.0	2
Unchecked CHEMBL612545	IC50	5.0	4.6267	10000.0	3
Enoyl-acyl-carrier protein reductase CHEMBL4150	IC50	4.9	4.9	12500.0	1
ADMET CHEMBL612558	IC50	4.8	4.8	16000.0	1
Human immunodeficiency virus type 1 integrase CHEMBL3471	IC50	4.7	4.7	19952.6	2
Enoyl-[acyl-carrier-protein] reductase [NADH] FabI CHEMBL1857	IC50	4.52	4.52	30000.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	4.46	4.46	35100.0	1
Nuclear factor NF-kappa-B complex CHEMBL2094258	IC50	4.42	4.42	38000.0	1
Proto-oncogene tyrosine-protein kinase Src CHEMBL267	IC50	4.19	4.19	65000.0	2
Leishmania donovani CHEMBL367	IC50	4.18	4.18	66000.0	1
Cyclin-dependent kinase 2 CHEMBL301	Kd	4.0	4.0	100000.0	1
Arginase-1 CHEMBL1075060	IC50	2.81	2.81	1551000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	6.7	ng.hr.mL-1	Mus musculus
AUC	251.0	ng.hr.mL-1	Mus musculus
AUC	141.0	ng.hr.mL-1	Mus musculus
Cmax	150.59	nM	Mus musculus
Cmax	2207.45	nM	Mus musculus
Cmax	304.86	nM	Mus musculus
F	37.0	%	Mus musculus
F	15.0	%	Mus musculus
Tmax	0.1	hr	Mus musculus
Tmax	0.3	hr	Mus musculus
Tmax	0.3	hr	Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Cyclooxygenase	IC50	=	4.6	nM	8.34	Inhibition of cyclooxygenase in rat RBL1 cells	-
Polyunsaturated fatty acid 5-lipoxygenase	IC50	=	4.6	nM	8.34	Inhibition of 5-lipoxygenase in rat RBL1 cells	-
Polyunsaturated fatty acid 5-lipoxygenase	IC50	=	4.6	nM	8.34	In vitro inhibition against 5-lipoxygenase in RBL-1 cells was determined	8254620
Enoyl-acyl-carrier protein reductase	Ki	=	14.0	nM	7.85	Inhibition of Plasmodium falciparum ENR in presence of triclosan	17263522
Aldo-keto reductase family 1 member B1	IC50	=	450.0	nM	6.35	Inhibition of Rattus norvegicus (rat) lens aldose reductase	-
Angiotensin-converting enzyme	IC50	=	730.0	nM	6.14	Inhibition of ACE in rabbit lung assessed as decrease in dansylglycine concentra...	20167484
Xanthine dehydrogenase/oxidase	IC50	=	1300.0	nM	5.89	Inhibition of bovine xanthine oxidase assessed as conversion of xanthine to uric...	26762836
Histone deacetylase 6	IC50	=	2146.0	nM	5.67	Determination of IC50 values for inhibition of enzymatic assay of human HDAC6 wi...	-
Enoyl-acyl-carrier protein reductase	Ki	=	2970.0	nM	5.53	Inhibition of Plasmodium falciparum ENR using crotonyl-CoA substrate	17263522
BV-2	IC50	=	4300.0	nM	5.37	Inhibition of LPS-induced NO production in mouse BV2 cells by Griess assay	27287369
RAW264.7	IC50	=	5300.0	nM	5.28	Inhibition of LPS-induced NO production in mouse RAW264.7 cells by Griess assay	27287369
Enoyl-acyl-carrier protein reductase	Ki	=	5500.0	nM	5.26	Inhibition of Plasmodium falciparum ENR using NADH substrate	17263522
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform	IC50	=	6400.0	nM	5.19	Inhibition of PI3Kalpha (unknown origin) by ADP-Glo kinase assay	35489224
17-beta-hydroxysteroid dehydrogenase type 2	IC50	=	7300.0	nM	5.14	Inhibition of human 17beta-HSD2 expressed in HEK293 cell lysates incubated for 1...	28319389
Epidermal growth factor receptor	IC50	=	8000.0	nM	5.1	Inhibition of EGFR	16441060
Unchecked	IC50	=	10000.0	nM	5.0	Inhibition of His-tagged Escherichia coli ANS1 FabG using acetoacetyl-CoA as sub...	37659218
BV-2	IC50	=	10900.0	nM	4.96	Antiinflammatory activity in mouse BV2 cells assessed as inhibition of LPS-induc...	28923363
BV-2	IC50	=	10900.0	nM	4.96	Antiinflammatory activity in mouse BV-2 cells assessed as reduction in LPS-induc...	37683361
Enoyl-acyl-carrier protein reductase	IC50	=	12500.0	nM	4.9	Inhibition of Plasmodium falciparum ENR	17263522
Epidermal growth factor receptor	IC50	=	16000.0	nM	4.8	Inhibition of EGFR	18680271

Literature References

PubMed	DOI	Target Context	# Activities
32361286	10.1016/j.ejmech.2020.112280	ADMET	15
32361286	10.1016/j.ejmech.2020.112280	Mus musculus	10
21493073	10.1016/j.bmc.2011.03.040	3T3-L1	5
37659218	10.1016/j.bmc.2023.117454	Unchecked	4
-	10.6019/CHEMBL4808148	Histone deacetylase 6	4
17263522	10.1021/jm061154d	Enoyl-acyl-carrier protein reductase	4
27815122	10.1016/j.bmcl.2016.10.072	HT-22	3
37659218	10.1016/j.bmc.2023.117454	Mycobacterium tuberculosis variant bovis	3
22743086	10.1016/j.bmc.2012.05.062	MDCK	3
32361286	10.1016/j.ejmech.2020.112280	No relevant target	3
19944611	10.1016/j.bmc.2009.11.015	No relevant target	3
31682126	10.1021/acs.jnatprod.9b00735	PANC-1	2
-	10.6019/CHEMBL4651402	SARS-CoV-2	2
18680271	10.1021/jm8002813	Unchecked	2
33412152	10.1016/j.bmcl.2021.127775	C2C12	2
-	10.6019/CHEMBL4495565	SARS-CoV-2	2
32361286	10.1016/j.ejmech.2020.112280	Unchecked	2
27815122	10.1016/j.bmcl.2016.10.072	Unchecked	2
38157838	10.1016/j.bmc.2023.117561	Unchecked	1
9822551	10.1021/jm980410m	Leishmania donovani	1

Data from ChEMBL 36 via Core Engine