Compound Detail

CHEMBL25948

SHOGAOL

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CCCCC/C=C/C(=O)CCc1ccc(O)c(OC)c1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL25948
Name	SHOGAOL
Phase	Preclinical
Structure Type	MOL
InChI Key	OQWKEEOHDMUXEO-BQYQJAHWSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

276.4

MW (Da)

4.04

ALogP

HBA

HBD

46.5

PSA (Å²)

0.55

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	C17H24O3
MW	276.38
Aromatic Rings	1
Heavy Atoms	20
NP-Likeness	1.54

Activity Summary

IC50 29 meas. best 6.54

EC50 2 meas. best 6.5

Ki 2 meas. best 4.97

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Transient receptor potential cation channel subfamily V member 1 CHEMBL4794	IC50	6.54	6.54	290.0	1
Transient receptor potential cation channel subfamily V member 1 CHEMBL4794	EC50	6.5	6.5	320.0	1
Cytochrome P450 1A2 CHEMBL3356	IC50	5.6	5.14	2500.0	2
Cytochrome P450 2C8 CHEMBL3721	IC50	5.54	5.54	2900.0	1
Cytochrome P450 2C9 CHEMBL3397	IC50	5.48	5.01	3300.0	2
Cytochrome P450 3A4 CHEMBL340	IC50	5.4	4.695	4000.0	4
BV-2 CHEMBL614781	IC50	5.25	5.25	5590.0	1
Cytochrome P450 2B6 CHEMBL4729	IC50	5.24	5.24	5800.0	1
Polyunsaturated fatty acid 5-lipoxygenase CHEMBL215	IC50	5.13	5.13	7400.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	5.1	4.8825	8000.0	4
No relevant target CHEMBL2362975	IC50	5.1	5.1	8000.0	1
Unchecked CHEMBL612545	IC50	5.1	5.1	7900.0	1
Unchecked CHEMBL612545	Ki	4.97	4.97	10780.0	1
Leukotriene A-4 hydrolase CHEMBL4618	IC50	4.9	4.755	12540.0	2
Transient receptor potential cation channel subfamily A member 1 CHEMBL5160	EC50	4.8	4.8	16000.0	1
Transient receptor potential cation channel subfamily A member 1 CHEMBL5160	IC50	4.78	4.78	16700.0	1
5-hydroxytryptamine receptor 1A CHEMBL214	Ki	4.74	4.74	18020.0	1
Cytochrome P450 2C19 CHEMBL3622	IC50	4.73	4.73	18800.0	1
Cytochrome P450 2E1 CHEMBL5281	IC50	4.12	4.06	76100.0	2
Cytochrome P450 2A6 CHEMBL5282	IC50	4.08	4.08	83300.0	1
HepG2 CHEMBL395	IC50	4.06	4.06	88000.0	1
Cytochrome P450 2D6 CHEMBL289	IC50	4.06	4.06	87000.0	1
ADMET CHEMBL612558	IC50	4.04	4.04	90400.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Transient receptor potential cation channel subfamily V member 1	IC50	=	290.0	nM	6.54	Antagonist activity at human TRPV1 ion channel expressed in HEK293 cells assesse...	22257892
Transient receptor potential cation channel subfamily V member 1	EC50	=	320.0	nM	6.5	Agonist activity at human TRPV1 ion channel expressed in HEK293 cells assessed a...	22257892
Cytochrome P450 1A2	IC50	=	2500.0	nM	5.6	Inhibition of CYP1A2 in human liver microsomes using phenacetin as substrate pre...	28274629
Cytochrome P450 2C8	IC50	=	2900.0	nM	5.54	Inhibition of CYP2C8 in human liver microsomes using amodiaquin as substrate pre...	28274629
Cytochrome P450 2C9	IC50	=	3300.0	nM	5.48	Inhibition of CYP2C9 in human liver microsomes using diclofenac as substrate pre...	28274629
Cytochrome P450 3A4	IC50	=	4000.0	nM	5.4	Inhibition of recombinant human CYP3A4 expressed in baculosomes using Vivid BOMR...	28274629
BV-2	IC50	=	5590.0	nM	5.25	Anti-inflammatory activity in mouse BV2 cells assessed as inhibition of LPS-indu...	30472026
Cytochrome P450 2B6	IC50	=	5800.0	nM	5.24	Inhibition of CYP2B6 in human liver microsomes using bupropion as substrate prei...	28274629
Polyunsaturated fatty acid 5-lipoxygenase	IC50	=	7400.0	nM	5.13	Inhibition of 5LOX	18976930
No relevant target	IC50	=	8000.0	nM	5.1	Antioxidant activity assessed as DPPH radical scavenging activity	22246389
NON-PROTEIN TARGET	IC50	=	8000.0	nM	5.1	Cytotoxicity against human H1299 cells assessed as growth inhibition after 24 hr...	22246389
Unchecked	IC50	=	7900.0	nM	5.1	Inhibition of AKT (unknown origin)	38295689
Cytochrome P450 3A4	IC50	=	8300.0	nM	5.08	Inhibition of CYP3A4 in human liver microsomes using testosterone as substrate p...	28274629
Unchecked	Ki	=	10780.0	nM	4.97	Inhibition of Brugia malayi thymidylate kinase using dTMP substrate by spectroph...	25659753
Leukotriene A-4 hydrolase	IC50	=	12540.0	nM	4.9	Inhibition of recombinant C-terminal His-tagged human LTA4H aminopeptidase activ...	28065501
NON-PROTEIN TARGET	IC50	=	12870.0	nM	4.89	Cytotoxicity against human HCT116 cells assessed as reduction in cell viability ...	28065501
NON-PROTEIN TARGET	IC50	=	15600.0	nM	4.81	Cytotoxicity in human OC2 cells assessed as decrease in cell viability after 24 ...	20669930
Transient receptor potential cation channel subfamily A member 1	EC50	=	16000.0	nM	4.8	Agonist activity at rat TRPA1 ion channel expressed in HEK293 cells assessed as ...	22257892
Transient receptor potential cation channel subfamily A member 1	IC50	=	16700.0	nM	4.78	Antagonist activity at rat TRPA1 ion channel expressed in HEK293 cells assessed ...	22257892
5-hydroxytryptamine receptor 1A	Ki	=	18020.0	nM	4.74	Displacement of [3H]8-OH-DPAT from 5HT1A receptor expressed in HEK293 cells afte...	20363635

Literature References

PubMed	DOI	Target Context	# Activities
22246389	10.1124/dmd.111.043331	ADMET	23
19271742	10.1021/np800555y	RBL-2H3	10
20669930	10.1021/np100213a	Unchecked	10
28110870	10.1016/j.bmcl.2016.12.042	SNU-182	7
22246389	10.1124/dmd.111.043331	Plasma	4
20363635	10.1016/j.bmc.2010.02.062	5-hydroxytryptamine receptor 1A	4
28065501	10.1016/j.bmc.2016.12.048	NON-PROTEIN TARGET	3
28274629	10.1016/j.bmcl.2017.02.047	Cytochrome P450 3A4	3
25156301	10.1016/j.bmc.2014.07.053	No relevant target	3
22257892	10.1016/j.bmcl.2011.12.113	Transient receptor potential cation channel subfamily A member 1	3
22257892	10.1016/j.bmcl.2011.12.113	Transient receptor potential cation channel subfamily V member 1	3
22246389	10.1124/dmd.111.043331	HCT-116	2
26706168	10.1016/j.bmcl.2015.12.004	C6	2
26988298	10.1016/j.bmcl.2016.03.023	C6	2
22246389	10.1124/dmd.111.043331	HT-29	2
20669930	10.1021/np100213a	NON-PROTEIN TARGET	2
19271742	10.1021/np800555y	ADMET	2
22246389	10.1124/dmd.111.043331	NCI-H1299	2
28065501	10.1016/j.bmc.2016.12.048	Leukotriene A-4 hydrolase	2
27700070	10.1021/acs.jnatprod.6b00582	C6	2

Data from ChEMBL 36 via Core Engine