Butyl sinapate

Details

• Internal ID: e5e95666-c221-4a8c-9583-61347185f55a
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: butyl (E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate
• SMILES (Canonical): CCCCOC(=O)C=CC1=CC(=C(C(=C1)OC)O)OC
• SMILES (Isomeric): CCCCOC(=O)/C=C/C1=CC(=C(C(=C1)OC)O)OC
• InChI: InChI=1S/C15H20O5/c1-4-5-8-20-14(16)7-6-11-9-12(18-2)15(17)13(10-11)19-3/h6-7,9-10,17H,4-5,8H2,1-3H3/b7-6+
• InChI Key: ADHXGGDIBVABLZ-VOTSOKGWSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₅
• Molecular Weight: 280.32 g/mol
• Exact Mass: 280.13107373 g/mol
• Topological Polar Surface Area (TPSA): 65.00 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 2.77
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 7

Synonyms

• 3,5-Dimethoxy-4-hydroxy-trans-cinnamic acid butyl ester

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9931	99.31%
Caco-2	+	0.8448	84.48%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.8386	83.86%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8552	85.52%
OATP1B3 inhibitior	+	0.9476	94.76%
MATE1 inhibitior	-	0.6800	68.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.5673	56.73%
P-glycoprotein inhibitior	-	0.9152	91.52%
P-glycoprotein substrate	-	0.7841	78.41%
CYP3A4 substrate	-	0.5199	51.99%
CYP2C9 substrate	-	0.6021	60.21%
CYP2D6 substrate	-	0.8411	84.11%
CYP3A4 inhibition	-	0.7439	74.39%
CYP2C9 inhibition	-	0.8417	84.17%
CYP2C19 inhibition	-	0.7243	72.43%
CYP2D6 inhibition	-	0.9071	90.71%
CYP1A2 inhibition	+	0.5087	50.87%
CYP2C8 inhibition	+	0.7327	73.27%
CYP inhibitory promiscuity	-	0.8373	83.73%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.7343	73.43%
Carcinogenicity (trinary)	Non-required	0.6872	68.72%
Eye corrosion	-	0.9836	98.36%
Eye irritation	+	0.7013	70.13%
Skin irritation	-	0.8020	80.20%
Skin corrosion	-	0.9785	97.85%
Ames mutagenesis	-	0.8700	87.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7469	74.69%
Micronuclear	-	0.8526	85.26%
Hepatotoxicity	-	0.6125	61.25%
skin sensitisation	-	0.5905	59.05%
Respiratory toxicity	-	0.8667	86.67%
Reproductive toxicity	-	0.5667	56.67%
Mitochondrial toxicity	-	0.9375	93.75%
Nephrotoxicity	-	0.7067	70.67%
Acute Oral Toxicity (c)	III	0.7443	74.43%
Estrogen receptor binding	+	0.8790	87.90%
Androgen receptor binding	+	0.6982	69.82%
Thyroid receptor binding	+	0.7140	71.40%
Glucocorticoid receptor binding	-	0.5997	59.97%
Aromatase binding	+	0.5734	57.34%
PPAR gamma	-	0.5145	51.45%
Honey bee toxicity	-	0.9744	97.44%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.9698	96.98%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.78%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.62%	96.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.94%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.93%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.99%	99.17%
CHEMBL2581	P07339	Cathepsin D	89.70%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.91%	95.56%
CHEMBL3194	P02766	Transthyretin	85.62%	90.71%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	84.72%	80.78%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	83.54%	97.21%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.81%	89.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.70%	90.71%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.56%	96.95%

Plants that contains it

• Tetradium ruticarpum

Cross-Links

• PubChem: 11808091
• NPASS: NPC302754