Eugenol acetate

Details

• Internal ID: 9a57ac87-749d-45d9-bd54-119ae23d56ed
• Taxonomy: Benzenoids > Phenol esters
• IUPAC Name: (2-methoxy-4-prop-2-enylphenyl) acetate
• SMILES (Canonical): CC(=O)OC1=C(C=C(C=C1)CC=C)OC
• SMILES (Isomeric): CC(=O)OC1=C(C=C(C=C1)CC=C)OC
• InChI: InChI=1S/C12H14O3/c1-4-5-10-6-7-11(15-9(2)13)12(8-10)14-3/h4,6-8H,1,5H2,2-3H3
• InChI Key: SCCDQYPEOIRVGX-UHFFFAOYSA-N
• Popularity: 268 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₄O₃
• Molecular Weight: 206.24 g/mol
• Exact Mass: 206.094294304 g/mol
• Topological Polar Surface Area (TPSA): 35.50 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 2.35
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

• EUGENYL ACETATE
• Acetyleugenol
• 93-28-7
• Aceteugenol
• 4-Allyl-2-methoxyphenyl acetate
• Acetyl eugenol
• 1,3,4-Eugenol acetate
• 4-Allyl-2-methoxyphenol acetate
• Aceto eugenol
• 1-Acetoxy-2-methoxy-4-allylbenzene
• Phenol, 2-methoxy-4-(2-propenyl)-, acetate
• Phenol, 4-allyl-2-methoxy-, acetate
• FEMA No. 2469
• 2-Methoxy-4-(2-propenyl)phenyl acetate
• NSC 1242
• EINECS 202-235-6
• 2-Methoxy-4-(2-propen-1-yl)phenyl acetate
• UNII-V9OSB376X8
• BRN 1964745
• V9OSB376X8
• 1,4-Eugenol acetate
• (2-methoxy-4-prop-2-enylphenyl) acetate
• AI3-01780
• NSC-1242
• Phenol, 2-methoxy-4-(2-propen-1-yl)-, 1-acetate
• CHEMBL108299
• DTXSID5052624
• CHEBI:34522
• 3-06-00-05029 (Beilstein Handbook Reference)
• Acetic acid 4-allyl-2-methoxy-phenyl ester
• 2-methoxy-4-(prop-2-en-1-yl)phenyl acetate
• EUGENOLACETATE
• Acetat
• acetate phenol
• acet eugenol
• 4-allyl-2-methoxy-
• acetyl eugenol fg 25
• bmse010055
• 1-acetate AI3-01780
• BRN 1964745 Phenol
• 4-allyl-2-methoxyphenylacetat
• BIDD:ER0670
• EUGENYL ACETATE [FCC]
• SCHEMBL112232
• 2-methoxy-4-(2-propenyl)-
• EUGENOL ACETATE [FHFI]
• EUGENYL ACETATE [INCI]
• DTXCID9031197
• FEMA 2469
• WLN: 1VOR BO1 D2U1
• Eugenyl acetate, >=98%, FCC
• NSC1242
• Acetyleugenol, analytical standard
• 2-methoxy-4-(2-propen-1-yl)-
• 11EUA7501
• BDBM50240728
• MFCD00026191
• s9377
• 1-acetoxy-2-methoxy-4-allyl benzene
• 3-(4-acetoxy-3-methoxyphenyl)propene
• AKOS015837940
• Eugenyl acetate, >=98%, FCC, FG
• CCG-266622
• CS-W015328
• HY-W014612
• LS-2753
• CHEMBL108299 V9OSB376X8
• 4 - allyl - 2 - methoxyphenyl acetate
• AS-56614
• 1-(3-methoxy-4-acetoxyphenyl)-2-propene
• 1-Acetoxy-2-methoxy-4-allylbenzene Phenol
• acetate NSC 1242 UNII-V9OSB376X8
• E0210
• FT-0626370
• Eugenol acetate 1000 microg/mL in Acetonitrile
• A844505
• Fenol, 2-metoxi-4-(2-propen-1-il)-, 1-acetato
• acetate 2-methoxy-4-(prop-2-en-1-yl)phenyl acetate
• Q27116129
• Z28076598
• 2-Methoxy-4-(prop-2-enyl)phenyl Acetate (Acetyleugenol)
• CHEBI:34522 SCCDQYPEOIRVGX-UHFFFAOYSA-N (2-methoxy-4-prop-2-enylphenyl)
• InChI=1/C12H14O3/c1-4-5-10-6-7-11(15-9(2)13)12(8-10)14-3/h4,6-8H,1,5H2,2-3H

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9961	99.61%
Caco-2	+	0.7380	73.80%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.8711	87.11%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9039	90.39%
OATP1B3 inhibitior	+	0.9779	97.79%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.6322	63.22%
P-glycoprotein inhibitior	-	0.9447	94.47%
P-glycoprotein substrate	-	0.8197	81.97%
CYP3A4 substrate	-	0.5580	55.80%
CYP2C9 substrate	-	0.8108	81.08%
CYP2D6 substrate	-	0.8045	80.45%
CYP3A4 inhibition	-	0.7406	74.06%
CYP2C9 inhibition	-	0.8912	89.12%
CYP2C19 inhibition	-	0.5839	58.39%
CYP2D6 inhibition	-	0.9379	93.79%
CYP1A2 inhibition	-	0.5728	57.28%
CYP2C8 inhibition	+	0.6850	68.50%
CYP inhibitory promiscuity	+	0.5128	51.28%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.6964	69.64%
Carcinogenicity (trinary)	Non-required	0.6079	60.79%
Eye corrosion	+	0.6816	68.16%
Eye irritation	+	0.9259	92.59%
Skin irritation	+	0.5512	55.12%
Skin corrosion	-	0.9413	94.13%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4396	43.96%
Micronuclear	-	0.6316	63.16%
Hepatotoxicity	+	0.8875	88.75%
skin sensitisation	-	0.8601	86.01%
Respiratory toxicity	-	0.9333	93.33%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	-	0.9875	98.75%
Nephrotoxicity	-	0.6382	63.82%
Acute Oral Toxicity (c)	III	0.8552	85.52%
Estrogen receptor binding	-	0.4928	49.28%
Androgen receptor binding	-	0.8835	88.35%
Thyroid receptor binding	-	0.7914	79.14%
Glucocorticoid receptor binding	-	0.7803	78.03%
Aromatase binding	-	0.5701	57.01%
PPAR gamma	-	0.8327	83.27%
Honey bee toxicity	-	0.6519	65.19%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.5652	56.52%
Fish aquatic toxicity	+	0.9858	98.58%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL221	P23219	Cyclooxygenase-1	3000 nM	IC50	PMID: 16038536

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.34%	96.09%
CHEMBL2581	P07339	Cathepsin D	94.11%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.28%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.86%	94.45%
CHEMBL1255126	O15151	Protein Mdm4	90.73%	90.20%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.16%	86.33%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	86.76%	95.50%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.77%	96.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	84.23%	91.11%
CHEMBL4208	P20618	Proteasome component C5	82.36%	90.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.76%	95.56%
CHEMBL2535	P11166	Glucose transporter	81.29%	98.75%

Plants that contains it

• Aconitum sajanense
• Alpinia chinensis
• Alpinia galanga
• Artemisia jacutica
• Bersama abyssinica
• Cinnamomum impressinervium
• Cinnamomum verum
• Damnacanthus major
• Duguetia confinis
• Etlingera cevuga
• Heterostemma brownii
• Jasminum sambac
• Laurus nobilis
• Myristica fragrans
• Myrtus communis
• Nepeta racemosa
• Pimenta racemosa
• Piper attenuatum
• Piper sylvestre
• Rubus sanctus
• Senna santanderensis
• Stauntonia hexaphylla
• Strychnos trinervis
• Syzygium aromaticum
• Zingiber officinale

Cross-Links

• PubChem: 7136
• NPASS: NPC303522
• ChEMBL: CHEMBL108299
• LOTUS: LTS0197690
• wikiData: Q104943089