Allyl cinnamate

Details

• Internal ID: a6c5cbca-2cb0-4c92-90f7-5874413da117
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Cinnamic acid esters
• IUPAC Name: prop-2-enyl (E)-3-phenylprop-2-enoate
• SMILES (Canonical): C=CCOC(=O)C=CC1=CC=CC=C1
• SMILES (Isomeric): C=CCOC(=O)/C=C/C1=CC=CC=C1
• InChI: InChI=1S/C12H12O2/c1-2-10-14-12(13)9-8-11-6-4-3-5-7-11/h2-9H,1,10H2/b9-8+
• InChI Key: KCMITHMNVLRGJU-CMDGGOBGSA-N
• Popularity: 20 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₂O₂
• Molecular Weight: 188.22 g/mol
• Exact Mass: 188.083729621 g/mol
• Topological Polar Surface Area (TPSA): 26.30 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 2.43
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

• 1866-31-5
• Propenyl cinnamate
• Vinyl carbinyl cinnamate
• CINNAMIC ACID, ALLYL ESTER
• 2-Propenoic acid, 3-phenyl-, 2-propenyl ester
• Allyl beta-phenylacrylate
• FEMA No. 2022
• 2-Propen-1-yl 3-phenyl-2-propenoate
• prop-2-enyl (E)-3-phenylprop-2-enoate
• 2-Propenoic acid, 3-phenyl-, 2-propen-1-yl ester
• NSC-20972
• N8149Z51V9
• DTXSID8047509
• prop-2-en-1-yl (2Z)-3-phenylprop-2-enoate
• RefChem:554853
• DTXCID6027509
• 217-477-8
• Allyl 3-phenylacrylate
• Cinnamic Acid Allyl Ester
• Allyl 3-phenyl-2-propenoate
• Allylester kyseliny skoricove
• MFCD00026105
• NSC 20972
• Allyl (E)-3-phenylprop-2-enoate
• 56289-56-6
• trans-Allyl cinnamate
• 2-Propenyl 3-phenyl-2-propenoate
• EINECS 217-477-8
• Allylester kyseliny skoricove [Czech]
• AI3-02313
• UNII-N8149Z51V9
• trans-Allylcinnamate
• Allyl cinnamate, >=99%
• SCHEMBL45456
• WLN: 1U2OV1U1R
• ALLYL CINNAMATE [FHFI]
• trans-cinnamic acid allyl ester
• CHEMBL2268886
• CHEBI:191535
• DTXSID301021113
• ALLYL .BETA.-PHENYLACRYLATE
• NSC20972
• Allyl cinnamate, analytical standard
• AKOS015894422
• Allyl Cinnamate (stabilized with TBC)
• (E)-3-phenyl-acrylic acid allyl ester
• CS-W016797
• DS-6431
• LS-14063
• NS00011939
• F240978
• Q27284688
• 2-aPropenoic acid, 3-aphenyl-a, 2-apropen-a1-ayl ester, (2E)a-
• InChI=1/C12H12O2/c1-2-10-14-12(13)9-8-11-6-4-3-5-7-11/h2-9H,1,10H2/b9-8

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9974	99.74%
Caco-2	+	0.9066	90.66%
Blood Brain Barrier	+	0.9250	92.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.5744	57.44%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9306	93.06%
OATP1B3 inhibitior	+	0.9620	96.20%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.5555	55.55%
P-glycoprotein inhibitior	-	0.9762	97.62%
P-glycoprotein substrate	-	0.9866	98.66%
CYP3A4 substrate	-	0.6609	66.09%
CYP2C9 substrate	-	0.6000	60.00%
CYP2D6 substrate	-	0.8653	86.53%
CYP3A4 inhibition	-	0.9127	91.27%
CYP2C9 inhibition	-	0.9031	90.31%
CYP2C19 inhibition	-	0.6943	69.43%
CYP2D6 inhibition	-	0.9442	94.42%
CYP1A2 inhibition	+	0.5875	58.75%
CYP2C8 inhibition	+	0.6496	64.96%
CYP inhibitory promiscuity	-	0.6561	65.61%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.5184	51.84%
Carcinogenicity (trinary)	Non-required	0.6972	69.72%
Eye corrosion	+	0.8810	88.10%
Eye irritation	+	0.9798	97.98%
Skin irritation	+	0.8886	88.86%
Skin corrosion	-	0.7924	79.24%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6172	61.72%
Micronuclear	-	0.9141	91.41%
Hepatotoxicity	-	0.5322	53.22%
skin sensitisation	+	0.9414	94.14%
Respiratory toxicity	-	0.8667	86.67%
Reproductive toxicity	-	0.8333	83.33%
Mitochondrial toxicity	-	0.9625	96.25%
Nephrotoxicity	+	0.4535	45.35%
Acute Oral Toxicity (c)	III	0.8614	86.14%
Estrogen receptor binding	-	0.6912	69.12%
Androgen receptor binding	+	0.6450	64.50%
Thyroid receptor binding	-	0.7355	73.55%
Glucocorticoid receptor binding	-	0.7154	71.54%
Aromatase binding	+	0.7404	74.04%
PPAR gamma	-	0.6343	63.43%
Honey bee toxicity	-	0.9034	90.34%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6151	61.51%
Fish aquatic toxicity	+	0.9793	97.93%

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	95.80%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.07%	91.11%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.97%	96.00%
CHEMBL221	P23219	Cyclooxygenase-1	91.21%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.71%	95.56%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	89.26%	94.62%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.68%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.15%	99.17%
CHEMBL5028	O14672	ADAM10	80.64%	97.50%
CHEMBL3401	O75469	Pregnane X receptor	80.07%	94.73%

Plants that contains it

• Styrax benzoin

Cross-Links

• PubChem: 641423
• NPASS: NPC176228