Methyl 4-prenyloxycinnamate

Details

• Internal ID: f15105da-fd78-43fa-b719-b32f18ac01f5
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Cinnamic acid esters
• IUPAC Name: methyl (E)-3-[4-(3-methylbut-2-enoxy)phenyl]prop-2-enoate
• SMILES (Canonical): CC(=CCOC1=CC=C(C=C1)C=CC(=O)OC)C
• SMILES (Isomeric): CC(=CCOC1=CC=C(C=C1)/C=C/C(=O)OC)C
• InChI: InChI=1S/C15H18O3/c1-12(2)10-11-18-14-7-4-13(5-8-14)6-9-15(16)17-3/h4-10H,11H2,1-3H3/b9-6+
• InChI Key: DBMLKNYVORYESN-RMKNXTFCSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₃
• Molecular Weight: 246.30 g/mol
• Exact Mass: 246.125594432 g/mol
• Topological Polar Surface Area (TPSA): 35.50 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 3.22
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 5

Synonyms

• 81053-49-8
• methyl (E)-3-[4-(3-methylbut-2-enoxy)phenyl]prop-2-enoate
• Methyl (E)-3-(4-((3-methylbut-2-en-1-yl)oxy)phenyl)acrylate
• CHEMBL2376526
• AKOS040762045

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.9257	92.57%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.9033	90.33%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9559	95.59%
OATP1B3 inhibitior	+	0.9456	94.56%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.7618	76.18%
P-glycoprotein inhibitior	-	0.9099	90.99%
P-glycoprotein substrate	-	0.9256	92.56%
CYP3A4 substrate	-	0.5258	52.58%
CYP2C9 substrate	-	0.7982	79.82%
CYP2D6 substrate	-	0.8644	86.44%
CYP3A4 inhibition	-	0.8998	89.98%
CYP2C9 inhibition	-	0.8902	89.02%
CYP2C19 inhibition	-	0.6544	65.44%
CYP2D6 inhibition	-	0.9062	90.62%
CYP1A2 inhibition	+	0.6911	69.11%
CYP2C8 inhibition	-	0.6846	68.46%
CYP inhibitory promiscuity	+	0.5319	53.19%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.6355	63.55%
Carcinogenicity (trinary)	Non-required	0.6739	67.39%
Eye corrosion	-	0.9514	95.14%
Eye irritation	+	0.7211	72.11%
Skin irritation	-	0.7017	70.17%
Skin corrosion	-	0.9900	99.00%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6895	68.95%
Micronuclear	-	0.7826	78.26%
Hepatotoxicity	-	0.6625	66.25%
skin sensitisation	-	0.6028	60.28%
Respiratory toxicity	-	0.6556	65.56%
Reproductive toxicity	-	0.5000	50.00%
Mitochondrial toxicity	-	0.8625	86.25%
Nephrotoxicity	+	0.5355	53.55%
Acute Oral Toxicity (c)	III	0.6991	69.91%
Estrogen receptor binding	+	0.6461	64.61%
Androgen receptor binding	+	0.7246	72.46%
Thyroid receptor binding	-	0.5937	59.37%
Glucocorticoid receptor binding	-	0.7316	73.16%
Aromatase binding	+	0.8152	81.52%
PPAR gamma	-	0.6965	69.65%
Honey bee toxicity	-	0.9303	93.03%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	+	0.9851	98.51%

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	95.85%	96.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.63%	91.11%
CHEMBL4208	P20618	Proteasome component C5	93.34%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.28%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.17%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.08%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	91.22%	90.17%
CHEMBL3401	O75469	Pregnane X receptor	87.75%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.51%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.75%	95.56%

Plants that contains it

• Cotula australis
• Eriostemon australasius
• Hemizonia congesta
• Lithospermum erythrorhizon
• Zanthoxylum wutaiense

Cross-Links

• PubChem: 14414116
• NPASS: NPC176971
• LOTUS: LTS0203780
• wikiData: Q104974584