3-methoxy-6-[(E)-2-(3,4,5-trimethoxyphenyl)ethenyl]benzene-1,2-diol

Details

• Internal ID: 5becf8be-bb1d-441d-b1be-f222bc8e57e7
• Taxonomy: Phenylpropanoids and polyketides > Stilbenes
• IUPAC Name: 3-methoxy-6-[(E)-2-(3,4,5-trimethoxyphenyl)ethenyl]benzene-1,2-diol
• SMILES (Canonical): COC1=C(C(=C(C=C1)C=CC2=CC(=C(C(=C2)OC)OC)OC)O)O
• SMILES (Isomeric): COC1=C(C(=C(C=C1)/C=C/C2=CC(=C(C(=C2)OC)OC)OC)O)O
• InChI: InChI=1S/C18H20O6/c1-21-13-8-7-12(16(19)17(13)20)6-5-11-9-14(22-2)18(24-4)15(10-11)23-3/h5-10,19-20H,1-4H3/b6-5+
• InChI Key: YUSYSJSHVJULID-AATRIKPKSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₀O₆
• Molecular Weight: 332.30 g/mol
• Exact Mass: 332.12598835 g/mol
• Topological Polar Surface Area (TPSA): 77.40 Ų
• XlogP: 3.40
• Atomic LogP (AlogP): 3.30
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

• CHEMBL520204
• Q5150953

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9739	97.39%
Caco-2	+	0.8528	85.28%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7063	70.63%
OATP2B1 inhibitior	-	0.8621	86.21%
OATP1B1 inhibitior	+	0.9181	91.81%
OATP1B3 inhibitior	+	0.9604	96.04%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.7069	70.69%
P-glycoprotein inhibitior	-	0.5615	56.15%
P-glycoprotein substrate	-	0.9424	94.24%
CYP3A4 substrate	-	0.5581	55.81%
CYP2C9 substrate	-	0.5969	59.69%
CYP2D6 substrate	-	0.6932	69.32%
CYP3A4 inhibition	-	0.6303	63.03%
CYP2C9 inhibition	-	0.8719	87.19%
CYP2C19 inhibition	-	0.7454	74.54%
CYP2D6 inhibition	-	0.8788	87.88%
CYP1A2 inhibition	+	0.7491	74.91%
CYP2C8 inhibition	+	0.8289	82.89%
CYP inhibitory promiscuity	+	0.6245	62.45%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.7894	78.94%
Carcinogenicity (trinary)	Non-required	0.5746	57.46%
Eye corrosion	-	0.9783	97.83%
Eye irritation	-	0.5870	58.70%
Skin irritation	-	0.7694	76.94%
Skin corrosion	-	0.9042	90.42%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4354	43.54%
Micronuclear	+	0.6100	61.00%
Hepatotoxicity	-	0.6305	63.05%
skin sensitisation	-	0.6935	69.35%
Respiratory toxicity	-	0.8778	87.78%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	-	0.7875	78.75%
Nephrotoxicity	-	0.7270	72.70%
Acute Oral Toxicity (c)	III	0.6637	66.37%
Estrogen receptor binding	+	0.8154	81.54%
Androgen receptor binding	+	0.7655	76.55%
Thyroid receptor binding	+	0.8399	83.99%
Glucocorticoid receptor binding	+	0.6914	69.14%
Aromatase binding	+	0.6888	68.88%
PPAR gamma	-	0.5131	51.31%
Honey bee toxicity	-	0.9035	90.35%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.6200	62.00%
Fish aquatic toxicity	+	0.9836	98.36%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.97%	96.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.07%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.05%	86.33%
CHEMBL3194	P02766	Transthyretin	94.04%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.71%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.60%	96.09%
CHEMBL1255126	O15151	Protein Mdm4	86.67%	90.20%
CHEMBL2487	P05067	Beta amyloid A4 protein	85.62%	96.74%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.43%	89.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	84.99%	89.62%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	84.93%	83.57%
CHEMBL3401	O75469	Pregnane X receptor	84.22%	94.73%
CHEMBL4355	O14976	Serine/threonine-protein kinase GAK	82.93%	89.32%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.56%	94.45%

Plants that contains it

• Combretum caffrum
• Combretum kraussii

Cross-Links

• PubChem: 6078282
• LOTUS: LTS0064835
• wikiData: Q5150953