4-Hydroxy-2-methoxy-3-(3-methylbut-2-enyl)-6-(2-phenylethyl)benzoic acid

Details

• Internal ID: eea688a6-894c-4d81-ac4c-c411817db422
• Taxonomy: Phenylpropanoids and polyketides > Stilbenes
• IUPAC Name: 4-hydroxy-2-methoxy-3-(3-methylbut-2-enyl)-6-(2-phenylethyl)benzoic acid
• SMILES (Canonical): CC(=CCC1=C(C=C(C(=C1OC)C(=O)O)CCC2=CC=CC=C2)O)C
• SMILES (Isomeric): CC(=CCC1=C(C=C(C(=C1OC)C(=O)O)CCC2=CC=CC=C2)O)C
• InChI: InChI=1S/C21H24O4/c1-14(2)9-12-17-18(22)13-16(19(21(23)24)20(17)25-3)11-10-15-7-5-4-6-8-15/h4-9,13,22H,10-12H2,1-3H3,(H,23,24)
• InChI Key: LWTSBJAZSUSNIF-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₄O₄
• Molecular Weight: 340.40 g/mol
• Exact Mass: 340.16745924 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 5.20
• Atomic LogP (AlogP): 4.39
• H-Bond Acceptor: 3
• 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	+	0.9863	98.63%
Caco-2	+	0.6262	62.62%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.8826	88.26%
OATP2B1 inhibitior	-	0.8539	85.39%
OATP1B1 inhibitior	+	0.8936	89.36%
OATP1B3 inhibitior	+	0.8409	84.09%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8710	87.10%
P-glycoprotein inhibitior	+	0.7310	73.10%
P-glycoprotein substrate	-	0.7346	73.46%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.6107	61.07%
CYP2D6 substrate	-	0.8739	87.39%
CYP3A4 inhibition	-	0.8444	84.44%
CYP2C9 inhibition	+	0.8071	80.71%
CYP2C19 inhibition	+	0.8562	85.62%
CYP2D6 inhibition	-	0.7059	70.59%
CYP1A2 inhibition	+	0.7448	74.48%
CYP2C8 inhibition	+	0.6458	64.58%
CYP inhibitory promiscuity	+	0.7826	78.26%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7425	74.25%
Carcinogenicity (trinary)	Non-required	0.7143	71.43%
Eye corrosion	-	0.9927	99.27%
Eye irritation	+	0.6160	61.60%
Skin irritation	-	0.7908	79.08%
Skin corrosion	-	0.9570	95.70%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6846	68.46%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	+	0.5750	57.50%
skin sensitisation	-	0.7770	77.70%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.6358	63.58%
Acute Oral Toxicity (c)	III	0.5715	57.15%
Estrogen receptor binding	+	0.8670	86.70%
Androgen receptor binding	+	0.6535	65.35%
Thyroid receptor binding	+	0.5633	56.33%
Glucocorticoid receptor binding	+	0.7850	78.50%
Aromatase binding	+	0.5477	54.77%
PPAR gamma	+	0.9111	91.11%
Honey bee toxicity	-	0.8588	85.88%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.38%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.28%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.58%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	92.68%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.28%	96.09%
CHEMBL2535	P11166	Glucose transporter	91.43%	98.75%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.73%	99.17%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	90.62%	96.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.65%	95.56%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	89.59%	95.50%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	87.14%	94.62%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.73%	94.45%
CHEMBL1255126	O15151	Protein Mdm4	82.61%	90.20%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.97%	96.00%

Plants that contains it

• Amorpha fruticosa

Cross-Links

• PubChem: 25135578
• NPASS: NPC225173
• ChEMBL: CHEMBL491821
• LOTUS: LTS0184441
• wikiData: Q105158592