Butyl Cinnamate

Details

• Internal ID: b8ffb0a8-a765-4261-a5f4-7daea759a48f
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Cinnamic acid esters
• IUPAC Name: butyl (E)-3-phenylprop-2-enoate
• InChI: InChI=1S/C13H16O2/c1-2-3-11-15-13(14)10-9-12-7-5-4-6-8-12/h4-10H,2-3,11H2,1H3/b10-9+
• InChI Key: OHHIVLJVBNCSHV-MDZDMXLPSA-N
• Popularity: 97 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₆O₂
• Molecular Weight: 204.26 g/mol
• Exact Mass: 204.115029749 g/mol
• Topological Polar Surface Area (TPSA): 26.30 Ų
• XlogP: 3.90
• Atomic LogP (AlogP): 3.04
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 5

Synonyms

• n-Butyl cinnamate
• 538-65-8
• Eliminoxy
• Butyl (E)-cinnamate
• Cinnamic acid, butyl ester
• (E)-butyl cinnamate
• Cinnamic acid n-butyl ester
• n-Butyl phenylacrylate
• butyl (E)-3-phenylprop-2-enoate
• Butyl 3-phenyl-2-propenoate
• NSC 71966
• Cinnamate de n-butyle
• FEMA No. 2192
• 2-Propenoic acid, 3-phenyl-, butyl ester
• Butyl phenylacrylate
• Cinnamic acid butyl ester
• NSC-71966
• 52392-64-0
• Butyl 3-phenylpropenoate
• Butyl-beta-phenylacrylate
• 105581-25-7
• NSC71966
• 05Q793M6Z5
• Cinnamate de n-butyle [French]
• EINECS 208-699-6
• BRN 2328067
• 3-Phenyl-acrylic acid, butyl ester
• AI3-02025
• UNII-05Q793M6Z5
• butyl (2E)-3-phenylprop-2-enoate
• (E)-3-Phenyl-acrylic acid butyl ester
• (E)-n-butyl cinnamate
• 4-09-00-02008 (Beilstein Handbook Reference)
• SCHEMBL119510
• BUTYL CINNAMATE [FHFI]
• N-Butyl cinnamate, AldrichCPR
• butyl (E)-3-(phenyl)acrylate
• CHEMBL1911049
• BUTYL CINNAMATE [USP-RS]
• CHEBI:192913
• AKOS015965719
• AKOS040744567
• AC-20788
• BS-17544
• CINNAMIC ACID N-BUTYL ESTER [MI]
• CS-0090364
• trans-3-phenyl-prop-2-enoic acid butyl ester
• D82012
• W-204586
• Q27236133

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.9487	94.87%
Blood Brain Barrier	+	0.9000	90.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Plasma membrane	0.6210	62.10%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8957	89.57%
OATP1B3 inhibitior	+	0.9343	93.43%
MATE1 inhibitior	-	0.7000	70.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.6261	62.61%
P-glycoprotein inhibitior	-	0.9746	97.46%
P-glycoprotein substrate	-	0.9520	95.20%
CYP3A4 substrate	-	0.6113	61.13%
CYP2C9 substrate	+	0.5973	59.73%
CYP2D6 substrate	-	0.8720	87.20%
CYP3A4 inhibition	-	0.9192	91.92%
CYP2C9 inhibition	-	0.8793	87.93%
CYP2C19 inhibition	+	0.5676	56.76%
CYP2D6 inhibition	-	0.9111	91.11%
CYP1A2 inhibition	+	0.8583	85.83%
CYP2C8 inhibition	+	0.6326	63.26%
CYP inhibitory promiscuity	-	0.6060	60.60%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7400	74.00%
Carcinogenicity (trinary)	Non-required	0.5606	56.06%
Eye corrosion	+	0.5333	53.33%
Eye irritation	+	0.9579	95.79%
Skin irritation	+	0.8626	86.26%
Skin corrosion	-	0.9536	95.36%
Ames mutagenesis	-	0.8800	88.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6477	64.77%
Micronuclear	-	0.9900	99.00%
Hepatotoxicity	-	0.6000	60.00%
skin sensitisation	+	0.8634	86.34%
Respiratory toxicity	-	0.8778	87.78%
Reproductive toxicity	-	0.8667	86.67%
Mitochondrial toxicity	-	0.9875	98.75%
Nephrotoxicity	-	0.5751	57.51%
Acute Oral Toxicity (c)	III	0.9469	94.69%
Estrogen receptor binding	-	0.7564	75.64%
Androgen receptor binding	+	0.7654	76.54%
Thyroid receptor binding	-	0.6699	66.99%
Glucocorticoid receptor binding	-	0.8084	80.84%
Aromatase binding	+	0.6484	64.84%
PPAR gamma	-	0.7988	79.88%
Honey bee toxicity	-	0.9914	99.14%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9771	97.71%

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	97.63%	86.33%
CHEMBL221	P23219	Cyclooxygenase-1	96.03%	90.17%
CHEMBL2581	P07339	Cathepsin D	94.75%	98.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.14%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.73%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.78%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.64%	95.56%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	88.20%	94.62%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.83%	91.11%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	84.77%	91.71%
CHEMBL3359	P21462	Formyl peptide receptor 1	84.20%	93.56%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	82.20%	80.78%
CHEMBL5028	O14672	ADAM10	80.02%	97.50%

Plants that contains it

• Mandragora officinarum

Cross-Links

• PubChem: 5273465
• LOTUS: LTS0141543
• wikiData: Q27236133