Dihydroguaiaretic acid

Details

• Internal ID: f0d78b8f-995e-44e8-b894-50fa6775777e
• Taxonomy: Lignans, neolignans and related compounds > Dibenzylbutane lignans
• IUPAC Name: 4-[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): CC(CC1=CC(=C(C=C1)O)OC)C(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
• InChI Key: ADFOLUXMYYCTRR-UHFFFAOYSA-N
• Popularity: 51 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
• Atomic LogP (AlogP): 4.17
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 7

Synonyms

• 36469-60-0
• 4,4'-(2,3-dimethylbutane-1,4-diyl)bis(2-methoxyphenol)
• CCRIS 7923
• 4-[4-(4-hydroxy-3-methoxyphenyl)-2,3-dimethylbutyl]-2-methoxyphenol
• Phenol, 4,4'-(2,3-dimethyl-1,4-butanediyl)bis[2-methoxy-
• Dihydroguayaretic acid
• SCHEMBL9087980
• CHEMBL1976696
• ACon1_001505
• DTXSID30957790
• 4-butanediylDihydroguaiaretic acid
• ADFOLUXMYYCTRR-UHFFFAOYSA-N
• HMS3342F18
• BDBM50030892
• NSC705084
• AKOS032948494
• NSC-705084
• NCGC00180436-01
• NCI60_037533
• FT-0696052
• ( inverted exclamation markA)-Dihydroguaiaretic Acid
• BRD-A19129781-001-01-6
• Phenol,4'-(2,3-dimethyl-1,4-butanediyl)bis[2-methoxy-
• 4-[4-(4-hydroxy-3-methoxy-phenyl)-2,3-dimethyl-butyl]-2-methoxy-phenol
• 2,3-Dimethyl-1-(3'-methoxy-4'-hydroxyphenyl)-4-(3''-methoxy-4''hydroxyphenyl)butane

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9857	98.57%
Caco-2	+	0.8343	83.43%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.8389	83.89%
OATP2B1 inhibitior	-	0.8568	85.68%
OATP1B1 inhibitior	+	0.9255	92.55%
OATP1B3 inhibitior	+	0.8293	82.93%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.5625	56.25%
P-glycoprotein inhibitior	+	0.6992	69.92%
P-glycoprotein substrate	-	0.9105	91.05%
CYP3A4 substrate	-	0.6926	69.26%
CYP2C9 substrate	+	0.5965	59.65%
CYP2D6 substrate	+	0.4548	45.48%
CYP3A4 inhibition	-	0.6481	64.81%
CYP2C9 inhibition	-	0.5392	53.92%
CYP2C19 inhibition	+	0.7591	75.91%
CYP2D6 inhibition	+	0.5580	55.80%
CYP1A2 inhibition	+	0.6742	67.42%
CYP2C8 inhibition	+	0.4490	44.90%
CYP inhibitory promiscuity	+	0.5477	54.77%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.7367	73.67%
Carcinogenicity (trinary)	Non-required	0.6400	64.00%
Eye corrosion	-	0.9776	97.76%
Eye irritation	-	0.7303	73.03%
Skin irritation	-	0.8374	83.74%
Skin corrosion	-	0.9508	95.08%
Ames mutagenesis	-	0.8900	89.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9065	90.65%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	-	0.5000	50.00%
skin sensitisation	-	0.8027	80.27%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	-	0.5000	50.00%
Mitochondrial toxicity	-	0.7750	77.50%
Nephrotoxicity	-	0.8059	80.59%
Acute Oral Toxicity (c)	III	0.7506	75.06%
Estrogen receptor binding	+	0.7656	76.56%
Androgen receptor binding	+	0.6678	66.78%
Thyroid receptor binding	+	0.7050	70.50%
Glucocorticoid receptor binding	+	0.6735	67.35%
Aromatase binding	+	0.7571	75.71%
PPAR gamma	+	0.6780	67.80%
Honey bee toxicity	-	0.9435	94.35%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5351	53.51%
Fish aquatic toxicity	+	0.9953	99.53%

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
CHEMBL3194	P02766	Transthyretin	6300 nM	EC50	PMID: 25314129

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

• Cinnamomum philippinense
• Endiandra anthropophagorum
• Eupomatia laurina
• Kadsura angustifolia
• Kadsura heteroclita
• Larrea tridentata
• Leucas aspera
• Machilus edulis
• Machilus thunbergii
• Machilus wangchiana
• Magnolia ovata
• Myristica argentea
• Myristica fragrans
• Ocotea heterochroma
• Pycnanthus angolensis
• Saururus cernuus
• Saururus chinensis
• Schisandra lancifolia
• Schisandra rubriflora

Cross-Links

• PubChem: 161924
• NPASS: NPC165133
• ChEMBL: CHEMBL1976696
• LOTUS: LTS0231938
• wikiData: Q82938265