Compound Detail

CHEMBL52

NORDIHYDROGUAIARETIC ACID

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CC(Cc1ccc(O)c(O)c1)C(C)Cc1ccc(O)c(O)c1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL52
Name	NORDIHYDROGUAIARETIC ACID
Phase	Preclinical
Structure Type	MOL
InChI Key	HCZKYJDFEPMADG-UHFFFAOYSA-N

Targets

158

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

302.4

MW (Da)

3.57

ALogP

HBA

HBD

80.9

PSA (Å²)

0.64

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	C18H22O4
MW	302.37
Aromatic Rings	2
Heavy Atoms	22
NP-Likeness	0.69

Activity Summary

IC50 145 meas. best 8.1

EC50 13 meas. best 5.63

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Transcription factor AP1 CHEMBL2111421	IC50	8.1	8.1	7.9	1
Polyunsaturated fatty acid 5-lipoxygenase CHEMBL312	IC50	8.0	6.5077	10.0	13
Aromatase CHEMBL1978	IC50	7.96	7.96	11.0	1
Polyunsaturated fatty acid 5-lipoxygenase CHEMBL215	IC50	7.6	6.4731	25.0	13
Leukotriene B4 receptor 1 CHEMBL3911	IC50	7.07	7.07	85.0	1
Rattus norvegicus CHEMBL376	IC50	7.0	7.0	100.0	1
Polyunsaturated fatty acid lipoxygenase ALOX15 CHEMBL4358	IC50	6.96	6.96	110.0	1
Polyunsaturated fatty acid lipoxygenase ALOX12 CHEMBL3687	IC50	6.96	5.8517	110.0	6
Polyunsaturated fatty acid lipoxygenase ALOX15 CHEMBL2903	IC50	6.96	6.15	110.0	9
Seed linoleate 13S-lipoxygenase-1 CHEMBL4586	IC50	6.75	5.612	180.0	5
Alpha-synuclein CHEMBL6152	IC50	6.68	6.67	210.0	2
Homo sapiens CHEMBL372	IC50	6.52	5.81	300.0	2
17-beta-hydroxysteroid dehydrogenase type 2 CHEMBL2789	IC50	6.42	6.42	380.0	1
Polyunsaturated fatty acid 5-lipoxygenase CHEMBL5211	IC50	6.4	6.4	400.0	1
Arachidonate 5-lipoxygenase CHEMBL2980	IC50	6.4	6.2	400.0	2
PMNL CHEMBL613706	IC50	6.4	6.4	400.0	1
Unchecked CHEMBL612545	IC50	6.35	5.071	450.0	29
Lipoxygenase CHEMBL1641359	IC50	6.3	4.946	500.0	5
Insulin-like growth factor 1 receptor CHEMBL1957	IC50	6.05	6.05	900.0	1
Liposome CHEMBL614676	IC50	5.7	5.7	2000.0	1
HL-60 CHEMBL383	IC50	5.64	5.275	2300.0	2
Heat shock factor protein 1 CHEMBL5313	EC50	5.63	5.63	2319.0	1
Psychosine receptor CHEMBL3714081	IC50	5.63	5.63	2334.3	1
Replicase polyprotein 1ab CHEMBL4523582	IC50	5.59	5.59	2590.0	1
Heat shock protein HSP90 CHEMBL2095165	IC50	5.58	5.58	2623.2	1
N-formyl peptide receptor 3 CHEMBL5646	IC50	5.52	5.52	3034.2	1
Glucose-dependent insulinotropic receptor CHEMBL5652	IC50	5.45	5.45	3545.3	1
G-protein coupled receptor 183 CHEMBL3259470	IC50	5.44	5.44	3634.8	1
Plasmodium falciparum CHEMBL364	IC50	5.4	5.0714	3981.1	7
Radical scavenging activity CHEMBL613712	IC50	5.38	5.2667	4200.0	3
NCI-H69 CHEMBL614805	IC50	5.36	5.36	4400.0	1
Transient receptor potential cation channel subfamily A member 1 CHEMBL6007	EC50	5.31	4.74	4900.0	3
17-beta-hydroxysteroid dehydrogenase type 1 CHEMBL3181	IC50	5.26	5.26	5500.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	5.22	4.7667	6000.0	3
Transthyretin CHEMBL3194	EC50	5.14	5.0367	7300.0	3
MCF7 CHEMBL387	IC50	5.07	4.84	8500.0	2
Zinc finger protein mex-5 CHEMBL1293319	EC50	5.06	5.06	8755.0	1
Unchecked CHEMBL612545	EC50	5.02	4.985	9480.0	2
Polyunsaturated fatty acid lipoxygenase ALOX15B CHEMBL2457	IC50	4.96	4.915	11000.0	2
Cyclooxygenase CHEMBL2096674	IC50	4.85	4.85	14000.0	1
L929 CHEMBL612267	EC50	4.72	4.635	19000.0	2
No relevant target CHEMBL2362975	IC50	4.68	4.68	20750.0	1
Estrogen receptor CHEMBL206	IC50	4.65	4.65	22193.7	1
RNA-binding protein pos-1 CHEMBL1293304	EC50	4.58	4.58	26111.0	1
Glucose-6-phosphate dehydrogenase-6-phosphogluconolactonase CHEMBL1741212	IC50	4.54	4.3233	29200.0	3
Plasmodium yoelii yoelii CHEMBL612328	IC50	4.52	4.52	30000.0	1
Cyclooxygenase CHEMBL2095157	IC50	4.52	4.52	30000.0	1
Androgen receptor CHEMBL1871	IC50	4.41	4.41	38800.0	1
MGC-803 CHEMBL3706566	IC50	4.34	4.34	45800.0	1
Fatty acid hydroperoxide lyase, chloroplastic CHEMBL4105968	IC50	4.3	4.3	50000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
T1/2	3.0	hr	-
T1/2	3.94	hr	-

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Transcription factor AP1	IC50	=	7.9	nM	8.1	Inhibition of Fos-Jun dimer formation (unknown origin)	24831826
Polyunsaturated fatty acid 5-lipoxygenase	IC50	=	10.0	nM	8.0	Inhibition of 5-lipoxygenase from rat basophilic leukemia(RBL-1) cells	-
Aromatase	IC50	=	11.0	nM	7.96	Inhibition of human placental microsome CYP19	20413308
Polyunsaturated fatty acid 5-lipoxygenase	IC50	=	25.0	nM	7.6	Inhibition of recombinant human 5-LOX in human PBML assessed as inhibition of A2...	21958737
Leukotriene B4 receptor 1	IC50	=	85.0	nM	7.07	The compound was tested for its inhibitory activity against LTB4 in human PMN	1313879
Polyunsaturated fatty acid 5-lipoxygenase	IC50	=	85.0	nM	7.07	Concentration required for 50 % inhibition of leukotriene B4 production in human...	2542553
Polyunsaturated fatty acid 5-lipoxygenase	IC50	=	97.0	nM	7.01	Inhibition of human 5-Lipoxygenase using H2DCFDA as substrate preincubated for 5...	32018096
Polyunsaturated fatty acid 5-lipoxygenase	IC50	=	100.0	nM	7.0	Inhibition of human 5-lipoxygenase using arachidonic acid as substrate pretreate...	30025348
Rattus norvegicus	IC50	=	100.0	nM	7.0	Inhibitory activity against peroxidation of rat cardiac membrane liposomes	-
Polyunsaturated fatty acid 5-lipoxygenase	IC50	=	100.0	nM	7.0	In vitro inhibition against 5-lipoxygenase in RBL-1 cells was determined	8254620
Polyunsaturated fatty acid lipoxygenase ALOX15	IC50	=	110.0	nM	6.96	Inhibition of human reticulocyte 12/15-lipoxygenase using arachidonic acid/linol...	24684213
Polyunsaturated fatty acid lipoxygenase ALOX12	IC50	=	110.0	nM	6.96	Inhibition of human platelet-type 12-lipoxygenase	21739938
Polyunsaturated fatty acid 5-lipoxygenase	IC50	=	110.0	nM	6.96	Inhibition of human N-terminal His6-tagged 5-lipoxygenase arachidonic acid by UV...	19848434
Polyunsaturated fatty acid lipoxygenase ALOX15	IC50	=	110.0	nM	6.96	Inhibition of His-tagged human reticulocyte 15-lipoxygenase	12608855
Polyunsaturated fatty acid lipoxygenase ALOX15	IC50	=	110.0	nM	6.96	Inhibitory concentration against isolated rabbit reticulocyte 15-lipoxygenase me...	15713402
Polyunsaturated fatty acid lipoxygenase ALOX15	IC50	=	110.0	nM	6.96	Inhibitory activity against human reticulocyte 15-lipoxygenase (15-HLO)	12036375
Polyunsaturated fatty acid 5-lipoxygenase	IC50	=	120.0	nM	6.92	Inhibition of human 5-LOX in human peripheral blood mononuclear leukocytes asses...	21958738
Polyunsaturated fatty acid 5-lipoxygenase	IC50	=	120.0	nM	6.92	Inhibition of 5-lipoxygenase by measuring 5-HETE levels in RBL-1 cell-free super...	8568814
Polyunsaturated fatty acid 5-lipoxygenase	IC50	=	130.0	nM	6.89	Inhibition of 5LOX in human PBMC by EIA assay	17378609
Polyunsaturated fatty acid 5-lipoxygenase	IC50	=	140.0	nM	6.85	In vitro inhibition of RBL-1 5-lipoxygenase	3681891

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL4689842	HEK-293T	346
-	10.6019/CHEMBL4689842	Fibroblast	345
-	10.6019/CHEMBL4689842	U2OS	344
16472241	10.2174/1570163043334794	Hepatotoxicity	18
26439661	10.1016/j.bmc.2015.09.039	No relevant target	9
19734910	10.1038/nchembio.215	Plasmodium falciparum	7
21106277	10.1016/j.ejmech.2010.10.035	No relevant target	6
25314129	10.1021/jm500997m	Transthyretin	6
-	10.6019/CHEMBL4495564	Replicase polyprotein 1ab	5
-	10.6019/CHEMBL5209801	Glucagon-like peptide 1 receptor	5
-	10.6019/CHEMBL5209801	Glucose-dependent insulinotropic receptor	5
-	10.6019/CHEMBL5209801	Beta-2 adrenergic receptor	5
-	10.6019/CHEMBL5209801	Adhesion G-protein coupled receptor F1	5
-	10.6019/CHEMBL5209801	CX3C chemokine receptor 1	5
-	10.6019/CHEMBL5209801	Sphingosine 1-phosphate receptor 1	5
19232783	10.1016/j.ejmech.2008.12.027	NON-PROTEIN TARGET	5
19615898	10.1016/j.bmcl.2009.06.063	A-375	5
30878828	10.1016/j.ejmech.2019.02.074	Transient receptor potential cation channel subfamily A member 1	5
17444626	10.1021/jm061173n	NON-PROTEIN TARGET	5
-	10.6019/CHEMBL5209801	Free fatty acid receptor 4	5

Data from ChEMBL 36 via Core Engine