5-[(2S,3R)-4-(3,4-dimethoxyphenyl)-2,3-dimethyl-butyl]-2-methoxy-phenol

Details

• Internal ID: 35ef93b1-1ede-4af6-85b9-e0954b8934a7
• Taxonomy: Lignans, neolignans and related compounds > Dibenzylbutane lignans
• IUPAC Name: 5-[(2S,3R)-4-(3,4-dimethoxyphenyl)-2,3-dimethylbutyl]-2-methoxyphenol
• SMILES (Canonical): CC(CC1=CC(=C(C=C1)OC)O)C(C)CC2=CC(=C(C=C2)OC)OC
• SMILES (Isomeric): C[C@@H](CC1=CC(=C(C=C1)OC)O)[C@H](C)CC2=CC(=C(C=C2)OC)OC
• InChI: InChI=1S/C21H28O4/c1-14(10-16-6-8-19(23-3)18(22)12-16)15(2)11-17-7-9-20(24-4)21(13-17)25-5/h6-9,12-15,22H,10-11H2,1-5H3/t14-,15+/m0/s1
• InChI Key: LRXBLKKDUMOEFS-LSDHHAIUSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₈O₄
• Molecular Weight: 344.40 g/mol
• Exact Mass: 344.19875937 g/mol
• Topological Polar Surface Area (TPSA): 47.90 Ų
• XlogP: 5.30
• Atomic LogP (AlogP): 4.48
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 8

Synonyms

• (+/-)-5-[4-(3,4-Dimethoxyphenyl)-2,3-dimethylbutyl]-2-methoxyphenol
• 5-[(2S,3R)-4-(3,4-dimethoxyphenyl)-2,3-dimethyl-butyl]-2-methoxy-phenol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9819	98.19%
Caco-2	+	0.8472	84.72%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8464	84.64%
OATP2B1 inhibitior	-	0.8596	85.96%
OATP1B1 inhibitior	+	0.9118	91.18%
OATP1B3 inhibitior	+	0.9074	90.74%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7450	74.50%
P-glycoprotein inhibitior	+	0.7778	77.78%
P-glycoprotein substrate	-	0.7798	77.98%
CYP3A4 substrate	-	0.6265	62.65%
CYP2C9 substrate	+	0.5965	59.65%
CYP2D6 substrate	+	0.4548	45.48%
CYP3A4 inhibition	+	0.5908	59.08%
CYP2C9 inhibition	-	0.5743	57.43%
CYP2C19 inhibition	+	0.8204	82.04%
CYP2D6 inhibition	+	0.5817	58.17%
CYP1A2 inhibition	+	0.7057	70.57%
CYP2C8 inhibition	+	0.4493	44.93%
CYP inhibitory promiscuity	+	0.5792	57.92%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.6967	69.67%
Carcinogenicity (trinary)	Non-required	0.6365	63.65%
Eye corrosion	-	0.9767	97.67%
Eye irritation	-	0.6957	69.57%
Skin irritation	-	0.7898	78.98%
Skin corrosion	-	0.9404	94.04%
Ames mutagenesis	-	0.8700	87.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8999	89.99%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	-	0.5000	50.00%
skin sensitisation	-	0.8428	84.28%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	-	0.5667	56.67%
Mitochondrial toxicity	-	0.7875	78.75%
Nephrotoxicity	-	0.7520	75.20%
Acute Oral Toxicity (c)	III	0.6988	69.88%
Estrogen receptor binding	+	0.6503	65.03%
Androgen receptor binding	+	0.6040	60.40%
Thyroid receptor binding	+	0.6397	63.97%
Glucocorticoid receptor binding	-	0.4677	46.77%
Aromatase binding	+	0.6530	65.30%
PPAR gamma	+	0.6232	62.32%
Honey bee toxicity	-	0.9311	93.11%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5151	51.51%
Fish aquatic toxicity	+	0.9954	99.54%

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	97.57%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.61%	98.95%
CHEMBL1255126	O15151	Protein Mdm4	93.85%	90.20%
CHEMBL2535	P11166	Glucose transporter	90.97%	98.75%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.15%	99.17%
CHEMBL3492	P49721	Proteasome Macropain subunit	88.63%	90.24%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.19%	94.45%
CHEMBL4208	P20618	Proteasome component C5	87.67%	90.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.64%	91.11%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.26%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.83%	86.33%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	80.55%	92.68%

Plants that contains it

• Larrea tridentata

Cross-Links

• PubChem: 476860
• LOTUS: LTS0257166
• wikiData: Q105156368