Nordihydroguaiaretic Acid

Representations & DB's id
ChEBI:	CHEBI:7625
ChEMBL:	CHEMBL52
PubChem:	4534
IUPAC:	4-[4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diol
Standard InChI:	InChI=1S/C18H22O4/c1-11(7-13-3-5-15(19)17(21)9-13)12(2)8-14-4-6-16(20)18(22)10-14/h3-6,9-12,19-22H,7-8H2,1-2H3
Standard InChI Key:	HCZKYJDFEPMADG-UHFFFAOYSA-N
SMILES:	CC(C(Cc1ccc(c(c1)O)O)C)Cc1ccc(c(c1)O)O

Molecular propeties
AlogP:	3.57
Hydrogen bonds acceptors:	4
Hydrogen bonds donors:	4
Rotatable bonds:	5
Number of rings:	2
Molecular Weight:	302.15
Topological polar surface area:	80.9
Number of aromatic rings:	2
Fsp3:	0.333
Number of carbons:	18

Plant sources

Part of plant	Plant name	Ref.
Fructus	Schisandra chinensis

In vitro data

Activity Type	Activity Value	Target Name	UniProt ID
IC50	130 nM	Arachidonate 5-lipoxygenase	P09917
Others	10 %	Cyclooxygenase-2	P35354
IC50	50000 nM	Cyclooxygenase-2	P35354
IC50	110 nM	Arachidonate 15-lipoxygenase	P16050
IC50	180 nM	Arachidonate 12-lipoxygenase	P18054
IC50	35000 nM	Arachidonate 5-lipoxygenase	P09917
IC50	11 nM	Cytochrome P450 19A1	P11511
IC50	5900 nM	Arachidonate 12-lipoxygenase	P18054
IC50	1100 nM	Arachidonate 15-lipoxygenase	P16050
IC50	110 nM	Arachidonate 5-lipoxygenase	P09917
Potency	7943.3 nM	Prelamin-A/C	P02545
Potency	7943.3 nM	Nuclear factor NF-kappa-B p105 subunit	P19838
Potency	2238.7 nM	ATP-dependent DNA helicase Q1	P46063
Potency	2818.4 nM	ATP-dependent DNA helicase Q1	P46063
Potency	2511.9 nM	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Q99714
Potency	2511.9 nM	ATP-dependent DNA helicase Q1	P46063
Potency	22387.2 nM	Lysine-specific demethylase 4D-like	B2RXH2
Potency	7943.3 nM	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Q99714
Potency	14125.4 nM	Lysine-specific demethylase 4D-like	B2RXH2
Potency	35481.3 nM	Lysine-specific demethylase 4D-like	B2RXH2
Potency	91999.7 nM	Ras-related protein Rab-9A	P51151
Potency	2818.4 nM	Tyrosyl-DNA phosphodiesterase 1	Q9NUW8
Potency	1258.9 nM	Arachidonate 15-lipoxygenase	P16050
Potency	6309.6 nM	Cytochrome P450 2C19	P33261
Potency	15848.9 nM	Cytochrome P450 2C19	P33261
Potency	25118.9 nM	Microtubule-associated protein tau	P10636
Potency	17782.8 nM	Microtubule-associated protein tau	P10636
IC50	50000 nM	14-3-3 protein gamma	P61981
Potency	10000 nM	Aldehyde dehydrogenase 1A1	P00352
Potency	5011.9 nM	Hypoxia-inducible factor 1 alpha	Q16665
Potency	7943.3 nM	Hypoxia-inducible factor 1 alpha	Q16665
Potency	28183.8 nM	Aldehyde dehydrogenase 1A1	P00352
Potency	158.5 nM	Aldehyde dehydrogenase 1A1	P00352
Potency	84921.4 nM	Peripheral myelin protein 22	Q01453
Potency	100 nM	Arachidonate 15-lipoxygenase	P16050
Potency	631 nM	Arachidonate 15-lipoxygenase	P16050
Potency	7943.3 nM	Hypoxia-inducible factor 1 alpha	Q16665
Potency	5011.9 nM	Hypoxia-inducible factor 1 alpha	Q16665
Potency	18492.7 nM	Serine/threonine-protein kinase mTOR	P42345
Potency	2818.4 nM	Arachidonate 12-lipoxygenase	P18054
Potency	14125.4 nM	Arachidonate 12-lipoxygenase	P18054
IC50	22193.67 nM	Estrogen receptor alpha	P03372
Potency	39810.7 nM	MAP kinase ERK2	P28482
Potency	12589.3 nM	MAP kinase ERK2	P28482
Potency	7943.3 nM	Nuclear factor NF-kappa-B p105 subunit	P19838
Potency	31622.8 nM	Ubiquitin carboxyl-terminal hydrolase 2	O75604
Potency	11220.2 nM	ATP-dependent DNA helicase Q1	P46063
Potency	22387.2 nM	Bloom syndrome protein	P54132
Potency	12589.3 nM	15-hydroxyprostaglandin dehydrogenase [NAD+]	P15428
Potency	14125.4 nM	15-hydroxyprostaglandin dehydrogenase [NAD+]	P15428
Potency	3162.3 nM	15-hydroxyprostaglandin dehydrogenase [NAD+]	P15428
Potency	5011.9 nM	Thrombopoietin	P40225
Potency	25118.9 nM	Cellular tumor antigen p53	P04637
Potency	125.9 nM	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Q99714
Potency	31622.8 nM	Cellular tumor antigen p53	P04637
Potency	11220.2 nM	Alpha-galactosidase A	P06280
Potency	19952.6 nM	Cellular tumor antigen p53	P04637
Potency	1000 nM	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Q99714
Potency	22387.2 nM	Bloom syndrome protein	P54132
Potency	100 nM	Cytochrome P450 3A4	P08684
Potency	12589.3 nM	Cytochrome P450 3A4	P08684
Potency	25118.9 nM	Cytochrome P450 2D6	P10635
Potency	39810.7 nM	Cytochrome P450 2D6	P10635
Potency	12589.3 nM	Cytochrome P450 3A4	P08684
Potency	1584.9 nM	Cytochrome P450 2C9	P11712
Potency	44668.4 nM	ATP-dependent DNA helicase Q1	P46063
Potency	7079.5 nM	Geminin	O75496
Potency	5011.9 nM	Thrombopoietin	P40225
Potency	12589.3 nM	Cytochrome P450 2C9	P11712
Potency	794.3 nM	DNA polymerase beta	P06746
Potency	100 nM	Cytochrome P450 3A4	P08684
Potency	3662.6 nM	Nuclear factor erythroid 2-related factor 2	Q16236
Potency	22387.2 nM	Lysine-specific demethylase 4A	O75164
Potency	1258.9 nM	Arachidonate 15-lipoxygenase, type II	O15296
Potency	28183.8 nM	Histone acetyltransferase GCN5	Q92830
Potency	23778.1 nM	M-phase phosphoprotein 8	Q99549
Potency	1835.5 nM	Dopamine D1 receptor	P21728
Potency	25118.9 nM	M-phase phosphoprotein 8	Q99549
Potency	794.3 nM	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Q96KQ7
Potency	3981.1 nM	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Q96KQ7
Potency	31622.8 nM	Chromobox protein homolog 1	P83916
Potency	3162.3 nM	Arachidonate 15-lipoxygenase, type II	O15296
Potency	1584.9 nM	Arachidonate 15-lipoxygenase, type II	O15296
Potency	2238.7 nM	Aldehyde dehydrogenase 1A1	P00352
Potency	30131.3 nM	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	Q13526
Potency	20587.8 nM	ATPase family AAA domain-containing protein 5	Q96QE3
Potency	15848.9 nM	Dopamine D1 receptor	P21728
Potency	751.9 nM	Flap endonuclease 1	P39748
IC50	5100 nM	Arachidonate 15-lipoxygenase	P16050
IC50	110 nM	Arachidonate 12-lipoxygenase	P18054
IC50	25 nM	Arachidonate 5-lipoxygenase	P09917
IC50	120 nM	Arachidonate 5-lipoxygenase	P09917
IC50	38800 nM	Androgen Receptor	P10275
IC50	10000 nM	Androgen Receptor	P10275
IC50	50000 nM	Androgen Receptor	P10275
Potency	6513.1 nM	Geminin	O75496
Potency	12589.3 nM	Glutaminase kidney isoform, mitochondrial	O94925
Potency	5623.4 nM	Glutaminase kidney isoform, mitochondrial	O94925
Potency	31622.8 nM	Ataxin-2	Q99700
Potency	366.3 nM	Geminin	O75496
Potency	39810.7 nM	Ataxin-2	Q99700
Potency	17782.8 nM	Werner syndrome ATP-dependent helicase	Q14191
Others	10 %	Arachidonate 15-lipoxygenase, type II	O15296
Others	0 %	Arachidonate 15-lipoxygenase	P16050
Others	0 %	Arachidonate 12-lipoxygenase	P18054
Others	0 %	Arachidonate 15-lipoxygenase, type II	O15296
Others	0 %	Arachidonate 15-lipoxygenase	P16050
Others	0 %	Arachidonate 12-lipoxygenase	P18054
Others	0 %	Arachidonate 5-lipoxygenase	P09917
Others	56.6 %	Arachidonate 5-lipoxygenase	P09917
IC50	110 nM	Arachidonate 15-lipoxygenase	P16050
Others	1.5 %	Arachidonate 12-lipoxygenase	P18054
Others	23.1 %	Arachidonate 15-lipoxygenase	P16050
EC50	8500 nM	Transthyretin	P02766
EC50	12600 nM	Transthyretin	P02766
Others	20 %	Transthyretin	P02766
EC50	7300 nM	Transthyretin	P02766

Nordihydroguaiaretic Acid

Representations & DB's id

Molecular propeties

Plant sources

In vitro data