Nordihydroguaiaretic acid

Details

• Internal ID: d7d36c89-7b73-42a4-a580-1a4009837caf
• Taxonomy: Lignans, neolignans and related compounds > Dibenzylbutane lignans
• IUPAC Name: 4-[4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diol
• SMILES (Canonical): CC(CC1=CC(=C(C=C1)O)O)C(C)CC2=CC(=C(C=C2)O)O
• SMILES (Isomeric): CC(CC1=CC(=C(C=C1)O)O)C(C)CC2=CC(=C(C=C2)O)O
• 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
• InChI Key: HCZKYJDFEPMADG-UHFFFAOYSA-N
• Popularity: 2,851 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₂O₄
• Molecular Weight: 302.40 g/mol
• Exact Mass: 302.15180918 g/mol
• Topological Polar Surface Area (TPSA): 80.90 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 3.57
• H-Bond Acceptor: 4
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

• 500-38-9
• NDGA
• Dihydronorguaiaretic acid
• Actinex
• 4-[4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diol
• Norhydroguaiaretic acid
• Norguaiaretic acid, dihydro-
• 1,2-Benzenediol, 4,4'-(2,3-dimethyl-1,4-butanediyl)bis-
• Dinorguaiaretic acid, dihydro-
• NSC 4291
• 4,4'-(2,3-Dimethyltetramethylene)dipyrocatechol
• 2,3-Bis(3,4-dihydroxyphenylmethyl)butane
• CCRIS 1399
• nordihydroguaretic acid
• Pyrocatechol, 4,4'-(2,3-dimethyltetramethylene)di-
• 4,4'-(2,3-Dimethyl-1,4-butanediyl)bis(pyrocatechol)
• CHEMBL52
• EINECS 207-903-0
• NordihydroGuaiareticAcid-d6
• Norguaiaretic acid, dihydro
• NSC 682984
• Butane, 1,4-bis(3,4-dihydroxyphenyl)-2,3-dimethyl-
• AI3-23059
• MLS000069451
• CHEBI:7625
• DTXSID5022437
• nordihydroguaiaretic acid (ndga)
• beta,gamma-Dimethyl-alpha,delta-bis(3,4-dihydroxyphenyl)butane
• NSC4291
• CHX 100; Masoprocol; meso-NDGA
• nordihydroguaiaretate
• 1,4-Bis(3,4-dihydroxyphenyl)-2,3-dimethylbutane
• 2,3-Dimethyl-1,4-bis(3,4-dihydroxyphenyl)butane
• NSC682984
• 4,4'-(2,3-dimethylbutane-1,4-diyl)dibenzene-1,2-diol
• 4,4'-(2,3-Dimethyl-1,4-butanediyl)bis(1,2-benzenediol)
• 4,4'-(2,3-dimethylbutane-1,4-diyl)bis(benzene-1,2-diol)
• SMR000059049
• 4,4'-(2,3-Dimethyl-1,4-butanediyl)bis-1,2-benzenediol
• Actinex (TN)
• nordihydroguiaretic acid
• Masoprocol (USAN/INN)
• TNP00263
• NDGA;Masoprocol
• NCGC00015741-06
• MFCD00002206
• LOX inhibitor, N/A
• N 5023
• Spectrum_001146
• nordihydroguajaretic acid
• Nordihydroguaiaretic Acid, (R*,S*)-Isomer
• Spectrum5_000735
• D0U3YB
• cid_4534
• Oprea1_368609
• KBioGR_002349
• KBioSS_001626
• KBioSS_002352
• MLS002153435
• MLS006011710
• DivK1c_000999
• SCHEMBL135976
• DTXCID702437
• GTPL4265
• rel-4,4'-((2R,3S)-2,3-Dimethylbutane-1,4-diyl)bis(benzene-1,2-diol)
• BDBM32020
• HCZKYJDFEPMADG-UHFFFAOYSA-
• HMS503G19
• KBio1_000999
• KBio2_001626
• KBio2_002349
• KBio2_004194
• KBio2_004917
• KBio2_006762
• KBio2_007485
• KBio3_002828
• NDGA (Nordihydroguaiaretic acid)
• cMAP_000026
• NINDS_000999
• BP_36
• HMS2232L16
• HMS3370G10
• HMS3649M15
• BCP08590
• HY-N0198
• Tox21_302171
• 4-[4-(3,4-dihydroxyphenyl)-2,3-dimethyl-butyl]benzene-1,2-diol
• s3984
• STL570288
• AKOS003367978
• CCG-207935
• CS-1431
• SDCCGSBI-0050852.P002
• IDI1_000999
• NDGA - CAS 500-38-9
• SMP2_000272
• 4,3-Dimethyltetramethylene)dipyrocatechol
• NCGC00015741-04
• NCGC00015741-05
• NCGC00015741-08
• NCGC00015741-09
• NCGC00015741-13
• NCGC00089785-02
• NCGC00089785-03
• NCGC00255380-01
• AC-24202
• AS-58406
• CAS-500-38-9
• NCI60_003992
• WLN: QR BQ D1Y1&Y1&1R CQ DQ
• XN163193
• LS-136429
• NORDIHYDROGUAIARETIC ACID--PROHIBITED
• D0800
• FT-0606781
• Nordihydroguaiaretic acid, >=97.0% (HPLC)
• .beta.,.delta.-bis(3,4-dihydroxyphenyl)butane
• 4,3-Dimethyl-1,4-butanediyl)bis(pyrocatechol)
• F17140
• N-8500
• 1, 4,4'-(2,3-dimethyl-1,4-butanediyl)bis-
• Pyrocatechol,4'-(2,3-dimethyltetramethylene)di-
• A913176
• Butane,4-bis(3,4-dihydroxyphenyl)-2,3-dimethyl-
• SR-01000003007
• Q7050774
• SR-01000003007-2
• 4, 4'- (2, 3- dimethyltetramethylene)dipyrocatechol
• Z2065671207
• 4,4'-(2,3 Dimethyl-1,4-butanediyl)bis(1,2-benzenediol)
• 4,4'-(2,3-Dimethylbutane-1,4-diyl)di(benzene-1,2-diol)
• PYROCATECHOL,4'- (2,3-DIEMTHYLTETRAMETHYLENE) DI-
• 4-[4-(3,4-dihydroxyphenyl)-2,3-dimethyl-butyl]pyrocatechol
• .beta.,.gamma.-Dimethyl-.alpha.,.delta.-bis(3,4-dihydroxyphenyl)butane
• 4-[4-[3,4-bis(oxidanyl)phenyl]-2,3-dimethyl-butyl]benzene-1,2-diol
• Nordihydroguaiaretic acid, >=90% (HPLC), from Larrea divaricata (creosote bush)
• InChI=1/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

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9578	95.78%
Caco-2	+	0.7519	75.19%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8535	85.35%
OATP2B1 inhibitior	-	0.7071	70.71%
OATP1B1 inhibitior	+	0.9493	94.93%
OATP1B3 inhibitior	+	0.9316	93.16%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.6765	67.65%
P-glycoprotein inhibitior	-	0.7833	78.33%
P-glycoprotein substrate	-	0.9637	96.37%
CYP3A4 substrate	-	0.7868	78.68%
CYP2C9 substrate	-	0.5629	56.29%
CYP2D6 substrate	+	0.3661	36.61%
CYP3A4 inhibition	-	0.5833	58.33%
CYP2C9 inhibition	+	0.8891	88.91%
CYP2C19 inhibition	+	0.8628	86.28%
CYP2D6 inhibition	+	0.8262	82.62%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	-	0.9506	95.06%
CYP inhibitory promiscuity	+	0.5322	53.22%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.6737	67.37%
Carcinogenicity (trinary)	Non-required	0.6290	62.90%
Eye corrosion	-	0.9663	96.63%
Eye irritation	+	0.8463	84.63%
Skin irritation	-	0.6844	68.44%
Skin corrosion	-	0.6927	69.27%
Ames mutagenesis	-	0.8700	87.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9060	90.60%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	+	0.9125	91.25%
skin sensitisation	+	0.5000	50.00%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	-	0.5803	58.03%
Mitochondrial toxicity	-	0.6875	68.75%
Nephrotoxicity	-	0.7894	78.94%
Acute Oral Toxicity (c)	III	0.8109	81.09%
Estrogen receptor binding	+	0.7988	79.88%
Androgen receptor binding	+	0.8697	86.97%
Thyroid receptor binding	+	0.6475	64.75%
Glucocorticoid receptor binding	+	0.8063	80.63%
Aromatase binding	+	0.8289	82.89%
PPAR gamma	+	0.7519	75.19%
Honey bee toxicity	-	0.9480	94.80%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	12589.3 nM; 14125.4 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	10000 nM; 28183.8 nM; 158.5 nM; 158.5 nM	Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via Super-PRED
CHEMBL2524	P06280	Alpha-galactosidase A	11220.2 nM	Potency	via CMAUP
CHEMBL1871	P10275	Androgen Receptor	38800 nM	IC50	PMID: 22047606
CHEMBL3687	P18054	Arachidonate 12-lipoxygenase	2600 nM; 110 nM; 5100 nM; 180 nM; 5000 nM; 110 nM; 5900 nM	IC50; IC50; IC50; IC50; IC50; IC50; IC50	PMID: 17869117; via Super-PRED; PMID: 12036375; PMID: 12608855; DOI: 10.1016/0960-894X(95)00565-B; PMID: 21739938; PMID: 19848434
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	100 nM; 250 nM; 110 nM; 110 nM; 631 nM; 110 nM; 110 nM; 1100 nM	Potency; IC50; IC50; IC50; Potency; IC50; IC50; IC50	via Super-PRED; PMID: 17869117; via Super-PRED; PMID: 12608855; via Super-PRED; PMID: 12036375; PMID: 24684213; PMID: 19848434
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	85 nM; 380 nM; 120 nM; 110 nM; 130 nM; 25 nM; 160 nM	IC50; IC50; IC50; IC50; IC50; IC50; IC50	PMID: 2542553; PMID: 18976930; PMID: 21958738; PMID: 19848434; PMID: 17378609; PMID: 21958737; PMID: 2157009
CHEMBL1293236	P46063	ATP-dependent DNA helicase Q1	2238.7 nM; 2511.9 nM; 2818.4 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP
CHEMBL1293237	P54132	Bloom syndrome protein	22387.2 nM; 22387.2 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4096	P04637	Cellular tumor antigen p53	25118.9 nM; 19952.6 nM; 31622.8 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP
CHEMBL1978	P11511	Cytochrome P450 19A1	11 nM; 11 nM	IC50; IC50	via Super-PRED; PMID: 20413308
CHEMBL3356	P05177	Cytochrome P450 1A2	25118.86 nM	AC50	via CMAUP
CHEMBL3622	P33261	Cytochrome P450 2C19	15848.9 nM; 6309.6 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL3397	P11712	Cytochrome P450 2C9	12589.3 nM; 1584.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL289	P10635	Cytochrome P450 2D6	39810.7 nM; 25118.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	12589.3 nM; 100 nM; 12589.3 nM; 100 nM	Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL2392	P06746	DNA polymerase beta	794.3 nM; 794.3 nM	Potency; Potency	via CMAUP; via Super-PRED
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	125.9 nM; 2511.9 nM; 1000 nM; 125.9 nM	Potency; Potency; Potency; Potency	via Super-PRED; via CMAUP; via CMAUP; via CMAUP
CHEMBL2789	P37059	Estradiol 17-beta-dehydrogenase 2	380 nM	IC50	via Super-PRED
CHEMBL206	P03372	Estrogen receptor alpha	22193.67 nM	IC50	via CMAUP
CHEMBL1293278	O75496	Geminin	7079.5 nM	Potency	via CMAUP
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	5011.9 nM; 7943.3 nM; 7943.3 nM; 5011.9 nM	Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL1957	P08069	Insulin-like growth factor I receptor	900 nM	IC50	PMID: 17502145
CHEMBL3911	Q15722	Leukotriene B4 receptor 1	85 nM	IC50	PMID: 1313879
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	14125.4 nM; 35481.3 nM; 22387.2 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	39810.7 nM; 12589.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	17782.8 nM; 25118.9 nM; 15848.9 nM; 11220.2 nM	Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	7943.3 nM; 7943.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	7943.3 nM	Potency	via CMAUP
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	18492.7 nM	Potency	via CMAUP
CHEMBL1293256	P40225	Thrombopoietin	5011.9 nM; 5011.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL2111421	P05412	Transcription factor AP1	7.9 nM	IC50	via Super-PRED
CHEMBL3194	P02766	Transthyretin	7300 nM; 8500 nM	EC50; EC50	PMID: 25314129; PMID: 25314129
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	2818.4 nM	Potency	via CMAUP
CHEMBL1293227	O75604	Ubiquitin carboxyl-terminal hydrolase 2	31622.8 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	95.84%	91.49%
CHEMBL2581	P07339	Cathepsin D	95.64%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.82%	91.11%
CHEMBL3492	P49721	Proteasome Macropain subunit	92.81%	90.24%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.76%	96.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.51%	99.15%
CHEMBL4208	P20618	Proteasome component C5	87.85%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.93%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	82.28%	94.73%
CHEMBL1907594	P30926	Neuronal acetylcholine receptor; alpha3/beta4	81.13%	97.23%

Plants that contains it

• Larrea cuneifolia
• Larrea tridentata
• Schisandra chinensis

Cross-Links

• PubChem: 4534
• NPASS: NPC228343
• ChEMBL: CHEMBL52
• LOTUS: LTS0102771
• wikiData: Q7050774