4-[(2R,3S)-4-(3-hydroxy-4-methoxyphenyl)-2,3-dimethylbutyl]-2-methoxyphenol

Details

• Internal ID: 9318e370-dfba-4f18-8565-23fc8073191f
• Taxonomy: Lignans, neolignans and related compounds > Dibenzylbutane lignans
• IUPAC Name: 4-[(2R,3S)-4-(3-hydroxy-4-methoxyphenyl)-2,3-dimethylbutyl]-2-methoxyphenol
• SMILES (Canonical): CC(CC1=CC(=C(C=C1)OC)O)C(C)CC2=CC(=C(C=C2)O)OC
• SMILES (Isomeric): C[C@@H](CC1=CC(=C(C=C1)OC)O)[C@H](C)CC2=CC(=C(C=C2)O)OC
• InChI: InChI=1S/C20H26O4/c1-13(9-15-6-8-19(23-3)18(22)11-15)14(2)10-16-5-7-17(21)20(12-16)24-4/h5-8,11-14,21-22H,9-10H2,1-4H3/t13-,14+/m0/s1
• InChI Key: XFEICBDAXKWVBZ-UONOGXRCSA-N
• Popularity: 0 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

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9709	97.09%
Caco-2	+	0.8301	83.01%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8392	83.92%
OATP2B1 inhibitior	-	0.8550	85.50%
OATP1B1 inhibitior	+	0.9218	92.18%
OATP1B3 inhibitior	+	0.8615	86.15%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.5539	55.39%
P-glycoprotein inhibitior	+	0.6732	67.32%
P-glycoprotein substrate	-	0.8710	87.10%
CYP3A4 substrate	-	0.6352	63.52%
CYP2C9 substrate	+	0.5965	59.65%
CYP2D6 substrate	+	0.4548	45.48%
CYP3A4 inhibition	-	0.5166	51.66%
CYP2C9 inhibition	+	0.6201	62.01%
CYP2C19 inhibition	+	0.8636	86.36%
CYP2D6 inhibition	+	0.7078	70.78%
CYP1A2 inhibition	+	0.7507	75.07%
CYP2C8 inhibition	+	0.5196	51.96%
CYP inhibitory promiscuity	+	0.6541	65.41%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.6967	69.67%
Carcinogenicity (trinary)	Non-required	0.6425	64.25%
Eye corrosion	-	0.9798	97.98%
Eye irritation	-	0.6164	61.64%
Skin irritation	-	0.8091	80.91%
Skin corrosion	-	0.9356	93.56%
Ames mutagenesis	-	0.8400	84.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9217	92.17%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	-	0.5500	55.00%
skin sensitisation	-	0.8326	83.26%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	-	0.5556	55.56%
Mitochondrial toxicity	-	0.7125	71.25%
Nephrotoxicity	-	0.7552	75.52%
Acute Oral Toxicity (c)	III	0.7061	70.61%
Estrogen receptor binding	+	0.6665	66.65%
Androgen receptor binding	+	0.6818	68.18%
Thyroid receptor binding	+	0.6758	67.58%
Glucocorticoid receptor binding	-	0.4697	46.97%
Aromatase binding	+	0.7510	75.10%
PPAR gamma	+	0.6652	66.52%
Honey bee toxicity	-	0.9278	92.78%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5351	53.51%
Fish aquatic toxicity	+	0.9957	99.57%

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	97.66%	96.09%
CHEMBL2581	P07339	Cathepsin D	94.00%	98.95%
CHEMBL1255126	O15151	Protein Mdm4	93.70%	90.20%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.45%	91.11%
CHEMBL3492	P49721	Proteasome Macropain subunit	91.38%	90.24%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.36%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.23%	99.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.09%	99.15%
CHEMBL2535	P11166	Glucose transporter	88.98%	98.75%
CHEMBL4208	P20618	Proteasome component C5	87.50%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.44%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.06%	95.89%
CHEMBL1951	P21397	Monoamine oxidase A	83.35%	91.49%

Plants that contains it

• Larrea tridentata

Cross-Links

• PubChem: 10711507
• LOTUS: LTS0193749
• wikiData: Q105326969