Methyl 3-[4-acetyloxy-3-(4-hydroxy-3-methylbut-2-enyl)phenyl]prop-2-enoate

Details

• Internal ID: 0f04e463-47e5-4cdf-91cb-1a3fe5386704
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Cinnamic acid esters
• IUPAC Name: methyl 3-[4-acetyloxy-3-(4-hydroxy-3-methylbut-2-enyl)phenyl]prop-2-enoate
• SMILES (Canonical): CC(=CCC1=C(C=CC(=C1)C=CC(=O)OC)OC(=O)C)CO
• SMILES (Isomeric): CC(=CCC1=C(C=CC(=C1)C=CC(=O)OC)OC(=O)C)CO
• InChI: InChI=1S/C17H20O5/c1-12(11-18)4-7-15-10-14(6-9-17(20)21-3)5-8-16(15)22-13(2)19/h4-6,8-10,18H,7,11H2,1-3H3
• InChI Key: DJSPAYAVADGYBF-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₀O₅
• Molecular Weight: 304.34 g/mol
• Exact Mass: 304.13107373 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.28
• H-Bond Acceptor: 5
• 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	+	0.9865	98.65%
Caco-2	+	0.8497	84.97%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.8864	88.64%
OATP2B1 inhibitior	-	0.8568	85.68%
OATP1B1 inhibitior	+	0.9269	92.69%
OATP1B3 inhibitior	+	0.9329	93.29%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.6478	64.78%
P-glycoprotein inhibitior	-	0.8044	80.44%
P-glycoprotein substrate	-	0.7249	72.49%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.7979	79.79%
CYP2D6 substrate	-	0.8735	87.35%
CYP3A4 inhibition	+	0.5591	55.91%
CYP2C9 inhibition	-	0.6110	61.10%
CYP2C19 inhibition	+	0.5619	56.19%
CYP2D6 inhibition	-	0.7538	75.38%
CYP1A2 inhibition	+	0.6940	69.40%
CYP2C8 inhibition	+	0.5088	50.88%
CYP inhibitory promiscuity	-	0.6581	65.81%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.6611	66.11%
Carcinogenicity (trinary)	Non-required	0.7349	73.49%
Eye corrosion	-	0.9862	98.62%
Eye irritation	-	0.7778	77.78%
Skin irritation	-	0.7761	77.61%
Skin corrosion	-	0.9761	97.61%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6995	69.95%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	-	0.6125	61.25%
skin sensitisation	-	0.7453	74.53%
Respiratory toxicity	-	0.6222	62.22%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	-	0.6875	68.75%
Nephrotoxicity	-	0.5641	56.41%
Acute Oral Toxicity (c)	III	0.5213	52.13%
Estrogen receptor binding	+	0.7587	75.87%
Androgen receptor binding	+	0.6526	65.26%
Thyroid receptor binding	-	0.5920	59.20%
Glucocorticoid receptor binding	+	0.6201	62.01%
Aromatase binding	+	0.7144	71.44%
PPAR gamma	-	0.5568	55.68%
Honey bee toxicity	-	0.8480	84.80%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9973	99.73%

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	96.09%	96.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.01%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.44%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.62%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.60%	99.17%
CHEMBL2581	P07339	Cathepsin D	90.53%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	86.64%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.08%	94.45%
CHEMBL1951	P21397	Monoamine oxidase A	85.29%	91.49%
CHEMBL1255126	O15151	Protein Mdm4	83.66%	90.20%
CHEMBL2535	P11166	Glucose transporter	83.02%	98.75%
CHEMBL4208	P20618	Proteasome component C5	82.62%	90.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.31%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.43%	89.00%

Plants that contains it

• Artemisia xanthochroa

Cross-Links

• PubChem: 162904104
• LOTUS: LTS0057955
• wikiData: Q104982775