Dihydroguaiaretic acid, meso-

Details

• Internal ID: 859dc357-80f7-4a1a-ba6b-e11eee6006bd
• Taxonomy: Lignans, neolignans and related compounds > Dibenzylbutane lignans
• IUPAC Name: 4-[(2S,3R)-4-(4-hydroxy-3-methoxyphenyl)-2,3-dimethylbutyl]-2-methoxyphenol
• SMILES (Canonical): CC(CC1=CC(=C(C=C1)O)OC)C(C)CC2=CC(=C(C=C2)O)OC
• SMILES (Isomeric): C[C@H](CC1=CC(=C(C=C1)O)OC)[C@@H](C)CC2=CC(=C(C=C2)O)OC
• InChI: InChI=1S/C20H26O4/c1-13(9-15-5-7-17(21)19(11-15)23-3)14(2)10-16-6-8-18(22)20(12-16)24-4/h5-8,11-14,21-22H,9-10H2,1-4H3/t13-,14+
• InChI Key: ADFOLUXMYYCTRR-OKILXGFUSA-N
• Popularity: 63 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆O₄
• Molecular Weight: 330.40 g/mol
• Exact Mass: 330.18310931 g/mol
• Topological Polar Surface Area (TPSA): 58.90 Ų
• XlogP: 5.00

Synonyms

• Dihydroguaiaretic acid
• 66322-34-7
• Dihydroguaiaretic acid, meso-
• S81Z40PSJ4
• CHEBI:68169
• UNII-S81Z40PSJ4
• DTXSID301019954
• 4-[(2S,3R)-4-(4-hydroxy-3-methoxyphenyl)-2,3-dimethylbutyl]-2-methoxyphenol
• 4,4'-dihydroxy-3,3'-dimethoxylignan
• Guaiacol, 4,4'-(2,3-dimethyltetramethylene)di-, meso-
• Phenol, 4,4'-(2,3-dimethyl-1,4-butanediyl)bis(2-methoxy-, (R*,S*)-
• Phenol, 4,4'-(2,3-dimethyl-1,4-butanediyl)bis[2-methoxy-, (R*,S*)-
• REL-4,4'-((2R,3S)-2,3-dimethyl-1,4-butanediyl)bis(2-methoxyphenol)
• Phenol, 4,4'-((2R,3S)-2,3-dimethyl-1,4-butanediyl)bis(2-methoxy-, rel-
• 4,4'-((2R,3S)-2,3-Dimethylbutane-1,4-diyl)bis(2-methoxyphenol)
• 4,4'-[(2R,3S)-2,3-dimethylbutane-1,4-diyl]bis(2-methoxyphenol)
• Dihydroguaiareticacid
• Meso-Dihyroguaiareticacid
• Mesodihydroguaiaretic Acid
• MLS002473306
• SCHEMBL974725
• CHEMBL430464
• DTXCID201477814
• HMS2202B04
• HY-N6087
• MS-24966
• SMR001397390
• CS-0032514
• F82185
• Q27136661
• meso-1,4-Bis-(4-hydroxy-3-methoxyphenyl)-2,3-dimethylbutane
• 2,2'-Dimethoxy-4,4'-[rel-(2R,3S)-2,3-dimethylbutane- 1,4-diyl]diphenol
• 4-[(2r,3s)-3-[(4-hydroxy-3-methoxyphenyl)methyl]-2-methylbutyl]-2-methoxyphenol
• 4-[(2S,3R)-4-(4-hydroxy-3-methoxy-phenyl)-2,3-dimethyl-butyl]-2-methoxy-phenol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2789	P37059	Estradiol 17-beta-dehydrogenase 2	940 nM	IC50	via Super-PRED
CHEMBL2111421	P05412	Transcription factor AP1	210 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.02%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.13%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.69%	98.95%
CHEMBL3492	P49721	Proteasome Macropain subunit	91.22%	90.24%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.01%	99.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.71%	99.15%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.61%	94.45%
CHEMBL1255126	O15151	Protein Mdm4	89.52%	90.20%
CHEMBL2535	P11166	Glucose transporter	88.70%	98.75%
CHEMBL4208	P20618	Proteasome component C5	86.26%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.12%	86.33%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	83.11%	89.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.76%	95.89%

Plants that contains it

• Catalpa bignonioides
• Cirsium arvense var. integrifolium
• Entada phaseoloides
• Erymophyllum tenellum
• Esenbeckia nesiotica
• Hyptis tomentosa
• Ipomoea cristulata
• Kadsura angustifolia
• Kadsura heteroclita
• Larrea tridentata
• Leucas aspera
• Machilus edulis
• Machilus robusta
• Machilus thunbergii
• Machilus wangchiana
• Murraya koenigii
• Myristica argentea
• Myristica fragrans
• Nothofagus menziesii
• Ocotea heterochroma
• Pancratium trianthum
• Piper pedicellosum
• Rhodotypos scandens
• Saururus chinensis
• Schisandra chinensis
• Schisandra glaucescens
• Schisandra lancifolia
• Schisandra propinqua
• Schisandra rubriflora
• Xanthostemon oppositifolius

Cross-Links

• PubChem: 476856
• NPASS: NPC232316
• ChEMBL: CHEMBL430464
• LOTUS: LTS0242513
• wikiData: Q27136661