tetra-O-methyl nordihydroguaiaretic acid

Details

• Internal ID: 9bd02252-a380-4ef6-b95b-b1ce81bb3544
• Taxonomy: Lignans, neolignans and related compounds > Dibenzylbutane lignans
• IUPAC Name: 4-[4-(3,4-dimethoxyphenyl)-2,3-dimethylbutyl]-1,2-dimethoxybenzene
• SMILES (Canonical): CC(CC1=CC(=C(C=C1)OC)OC)C(C)CC2=CC(=C(C=C2)OC)OC
• SMILES (Isomeric): CC(CC1=CC(=C(C=C1)OC)OC)C(C)CC2=CC(=C(C=C2)OC)OC
• InChI: InChI=1S/C22H30O4/c1-15(11-17-7-9-19(23-3)21(13-17)25-5)16(2)12-18-8-10-20(24-4)22(14-18)26-6/h7-10,13-16H,11-12H2,1-6H3
• InChI Key: ORQFDHFZSMXRLM-UHFFFAOYSA-N
• Popularity: 43 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₀O₄
• Molecular Weight: 358.50 g/mol
• Exact Mass: 358.21440943 g/mol
• Topological Polar Surface Area (TPSA): 36.90 Ų
• XlogP: 5.60
• Atomic LogP (AlogP): 4.78
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 9

Synonyms

• Tmndga
• tetra-O-methyl nordihydroguaiaretic acid
• FW 358.2
• 4-[4-(3,4-dimethoxyphenyl)-2,3-dimethylbutyl]-1,2-dimethoxybenzene
• Tetra-O-methyl-ndga
• EM-1421
• Tetramethoxynordihydroguaiaretic acid
• Tetra-O-methylnordihydroguaiaretic acid
• NSC 136955
• Dimethyldihydroguaiaretic acid
• EM1421
• 4,4'-(2,3-Dimethyl-1,4-butanediyl)bis-1,2-dimethoxybenzene
• 1,1'-(2,3-Dimethyl-1,4-butanediyl)bis(3,4-dimethoxybenzene)
• 1,1'-(2,3-dimethylbutane-1,4-diyl)bis(3,4-dimethoxybenzene)
• meso-1,4-Bis(3,4-dimethoxyphenyl)dimethylbutane
• CHEMBL492149
• SCHEMBL2356280
• DTXSID10972502
• ORQFDHFZSMXRLM-UHFFFAOYSA-N
• Benzene, 1,1'-(2,3-dimethyl-1,4-butanediyl)bis(3,4-dimethoxy-
• ZAA15024
• NSC136955
• AKOS040744917
• NSC-136955
• Tetra-O-methyl-nordihydroguaiaretic acid
• 1,4-dimethoxyphentl)-2,3-dimethylbutane
• Butane,4-bis(3,4-dimethoxyphenyl)-2,3-dimethyl-
• Benzene,1'-(2,3-dimethyl-1,4-butanediyl)bis[3,4-dimethoxy]
• NCGC00384872-01!4-[4-(3,4-dimethoxyphenyl)-2,3-dimethylbutyl]-1,2-dimethoxybenzene

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9952	99.52%
Caco-2	+	0.8801	88.01%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.8143	81.43%
Subcellular localzation	Mitochondria	0.8166	81.66%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9284	92.84%
OATP1B3 inhibitior	+	0.9353	93.53%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8846	88.46%
P-glycoprotein inhibitior	+	0.8997	89.97%
P-glycoprotein substrate	-	0.7429	74.29%
CYP3A4 substrate	-	0.6826	68.26%
CYP2C9 substrate	+	0.5890	58.90%
CYP2D6 substrate	+	0.4546	45.46%
CYP3A4 inhibition	+	0.5621	56.21%
CYP2C9 inhibition	-	0.7437	74.37%
CYP2C19 inhibition	+	0.7484	74.84%
CYP2D6 inhibition	-	0.6434	64.34%
CYP1A2 inhibition	+	0.7847	78.47%
CYP2C8 inhibition	-	0.6624	66.24%
CYP inhibitory promiscuity	+	0.6816	68.16%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7267	72.67%
Carcinogenicity (trinary)	Non-required	0.5536	55.36%
Eye corrosion	-	0.9654	96.54%
Eye irritation	-	0.7606	76.06%
Skin irritation	-	0.8570	85.70%
Skin corrosion	-	0.9778	97.78%
Ames mutagenesis	-	0.8700	87.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9468	94.68%
Micronuclear	-	0.7741	77.41%
Hepatotoxicity	+	0.5034	50.34%
skin sensitisation	-	0.8480	84.80%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	-	0.5111	51.11%
Mitochondrial toxicity	-	0.8625	86.25%
Nephrotoxicity	-	0.7416	74.16%
Acute Oral Toxicity (c)	III	0.7434	74.34%
Estrogen receptor binding	+	0.7675	76.75%
Androgen receptor binding	+	0.5890	58.90%
Thyroid receptor binding	+	0.6444	64.44%
Glucocorticoid receptor binding	+	0.5773	57.73%
Aromatase binding	+	0.6658	66.58%
PPAR gamma	+	0.6124	61.24%
Honey bee toxicity	-	0.9166	91.66%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.9965	99.65%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.51%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.05%	98.95%
CHEMBL1255126	O15151	Protein Mdm4	93.23%	90.20%
CHEMBL2535	P11166	Glucose transporter	89.27%	98.75%
CHEMBL3492	P49721	Proteasome Macropain subunit	87.91%	90.24%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.97%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.83%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.77%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.35%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.98%	94.45%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	82.60%	89.62%
CHEMBL4208	P20618	Proteasome component C5	82.45%	90.00%
CHEMBL5747	Q92793	CREB-binding protein	81.51%	95.12%

Plants that contains it

• Otoba novogranatensis
• Schisandra rubriflora

Cross-Links

• PubChem: 97616
• LOTUS: LTS0009327
• wikiData: Q72509556