methyl (E)-3-[4-hydroxy-3,5-bis(3-methylbut-2-enyl)phenyl]prop-2-enoate

Details

• Internal ID: 01573018-8f55-4b56-9d26-5222308e00dc
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acid esters > Coumaric acid esters
• IUPAC Name: methyl (E)-3-[4-hydroxy-3,5-bis(3-methylbut-2-enyl)phenyl]prop-2-enoate
• SMILES (Canonical): CC(=CCC1=CC(=CC(=C1O)CC=C(C)C)C=CC(=O)OC)C
• SMILES (Isomeric): CC(=CCC1=CC(=CC(=C1O)CC=C(C)C)/C=C/C(=O)OC)C
• InChI: InChI=1S/C20H26O3/c1-14(2)6-9-17-12-16(8-11-19(21)23-5)13-18(20(17)22)10-7-15(3)4/h6-8,11-13,22H,9-10H2,1-5H3/b11-8+
• InChI Key: DKDGLQSOIBOYQO-DHZHZOJOSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆O₃
• Molecular Weight: 314.40 g/mol
• Exact Mass: 314.18819469 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 5.70
• Atomic LogP (AlogP): 4.60
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.8638	86.38%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.9161	91.61%
OATP2B1 inhibitior	-	0.7124	71.24%
OATP1B1 inhibitior	+	0.8812	88.12%
OATP1B3 inhibitior	+	0.9329	93.29%
MATE1 inhibitior	-	0.5600	56.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.9234	92.34%
P-glycoprotein inhibitior	-	0.6365	63.65%
P-glycoprotein substrate	-	0.8878	88.78%
CYP3A4 substrate	-	0.5716	57.16%
CYP2C9 substrate	+	0.5976	59.76%
CYP2D6 substrate	-	0.8619	86.19%
CYP3A4 inhibition	-	0.8850	88.50%
CYP2C9 inhibition	-	0.6274	62.74%
CYP2C19 inhibition	+	0.5397	53.97%
CYP2D6 inhibition	-	0.8834	88.34%
CYP1A2 inhibition	-	0.6604	66.04%
CYP2C8 inhibition	-	0.7745	77.45%
CYP inhibitory promiscuity	-	0.5335	53.35%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.6708	67.08%
Carcinogenicity (trinary)	Non-required	0.7451	74.51%
Eye corrosion	-	0.9512	95.12%
Eye irritation	+	0.8810	88.10%
Skin irritation	-	0.6106	61.06%
Skin corrosion	-	0.9691	96.91%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5356	53.56%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.6968	69.68%
skin sensitisation	-	0.6485	64.85%
Respiratory toxicity	-	0.6444	64.44%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	-	0.7500	75.00%
Nephrotoxicity	-	0.5784	57.84%
Acute Oral Toxicity (c)	III	0.7894	78.94%
Estrogen receptor binding	+	0.8782	87.82%
Androgen receptor binding	+	0.7048	70.48%
Thyroid receptor binding	+	0.6085	60.85%
Glucocorticoid receptor binding	+	0.7193	71.93%
Aromatase binding	+	0.7123	71.23%
PPAR gamma	+	0.8544	85.44%
Honey bee toxicity	-	0.9055	90.55%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.7000	70.00%
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
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.02%	91.11%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.83%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	92.73%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.19%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.99%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.65%	94.45%
CHEMBL2581	P07339	Cathepsin D	89.54%	98.95%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	87.54%	89.34%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.34%	99.17%
CHEMBL221	P23219	Cyclooxygenase-1	85.24%	90.17%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.74%	94.33%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.45%	96.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.56%	95.56%

Plants that contains it

• Flourensia heterolepis

Cross-Links

• PubChem: 11109821
• LOTUS: LTS0050002
• wikiData: Q104983042