4-Hydroxy-3-methoxycinnamic Acid Ethyl Ester

Details

• Internal ID: ba8206f1-fa22-4a52-9f05-59ae23ad328a
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: ethyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• SMILES (Canonical): CCOC(=O)C=CC1=CC(=C(C=C1)O)OC
• SMILES (Isomeric): CCOC(=O)C=CC1=CC(=C(C=C1)O)OC
• InChI: InChI=1S/C12H14O4/c1-3-16-12(14)7-5-9-4-6-10(13)11(8-9)15-2/h4-8,13H,3H2,1-2H3
• InChI Key: ATJVZXXHKSYELS-UHFFFAOYSA-N
• Popularity: 49 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₄O₄
• Molecular Weight: 222.24 g/mol
• Exact Mass: 222.08920892 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 1.98
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

• Ethyl (E)-ferulate
• MFCD00009190
• 3-Methoxy-4-hydroxycinnamic acid ethyl ester
• SCHEMBL73132
• ATJVZXXHKSYELS-UHFFFAOYSA-N
• DTXSID001021502
• SY019188
• E0739
• FT-0602358

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9921	99.21%
Caco-2	+	0.8630	86.30%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.9085	90.85%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9472	94.72%
OATP1B3 inhibitior	+	0.9788	97.88%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.5553	55.53%
P-glycoprotein inhibitior	-	0.9864	98.64%
P-glycoprotein substrate	-	0.9705	97.05%
CYP3A4 substrate	-	0.5666	56.66%
CYP2C9 substrate	-	0.7983	79.83%
CYP2D6 substrate	-	0.8558	85.58%
CYP3A4 inhibition	-	0.8163	81.63%
CYP2C9 inhibition	-	0.6592	65.92%
CYP2C19 inhibition	-	0.8177	81.77%
CYP2D6 inhibition	-	0.9153	91.53%
CYP1A2 inhibition	-	0.8186	81.86%
CYP2C8 inhibition	+	0.7411	74.11%
CYP inhibitory promiscuity	-	0.6512	65.12%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.7200	72.00%
Carcinogenicity (trinary)	Non-required	0.7219	72.19%
Eye corrosion	-	0.9305	93.05%
Eye irritation	+	0.9259	92.59%
Skin irritation	-	0.5247	52.47%
Skin corrosion	-	0.9683	96.83%
Ames mutagenesis	-	0.8100	81.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6191	61.91%
Micronuclear	-	0.6046	60.46%
Hepatotoxicity	-	0.7844	78.44%
skin sensitisation	-	0.6233	62.33%
Respiratory toxicity	-	0.9222	92.22%
Reproductive toxicity	+	0.5667	56.67%
Mitochondrial toxicity	-	0.9000	90.00%
Nephrotoxicity	-	0.7892	78.92%
Acute Oral Toxicity (c)	III	0.7711	77.11%
Estrogen receptor binding	+	0.8906	89.06%
Androgen receptor binding	+	0.6359	63.59%
Thyroid receptor binding	-	0.7291	72.91%
Glucocorticoid receptor binding	-	0.7945	79.45%
Aromatase binding	+	0.6401	64.01%
PPAR gamma	-	0.6621	66.21%
Honey bee toxicity	-	0.9441	94.41%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.5555	55.55%
Fish aquatic toxicity	+	0.9681	96.81%

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	96.74%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.79%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.96%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.71%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.43%	95.56%
CHEMBL3194	P02766	Transthyretin	90.20%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.07%	99.17%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	90.02%	89.62%
CHEMBL3401	O75469	Pregnane X receptor	86.68%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.20%	89.00%
CHEMBL4208	P20618	Proteasome component C5	84.44%	90.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.23%	96.95%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	82.31%	97.21%
CHEMBL2535	P11166	Glucose transporter	80.72%	98.75%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.13%	95.50%

Plants that contains it

• Acacia linarioides
• Achillea millefolium
• Alcea nudiflora
• Alocasia macrorrhizos
• Anadenanthera colubrina
• Anaphalis margaritacea
• Angelica sinensis
• Aquilegia viridiflora
• Astragalus kabadianus
• Boronia lanceolata
• Brombya platynema
• Campanula pendula
• Carissa spinarum
• Cerbera odollam
• Chloranthus holostegius
• Cichorium endivia
• Clerodendrum infortunatum
• Clinopodium gracile
• Coelogyne prolifera
• Corydalis crystallina
• Daphne arisanensis
• Denhamia disperma
• Eucalyptus campanulata
• Euphorbia cattimandoo
• Guadua angustifolia
• Hedychium coronarium
• Hemiphragma heterophyllum
• Ipomoea nil
• Jaborosa leucotricha
• Kiggelaria africana
• Lasianthus attenuatus var. attenuatus
• Lippia abyssinica
• Lomandra hastilis
• Lupinus luteus
• Mercurialis leiocarpa
• Micrandropsis scleroxylon
• Morinda morindoides
• Morisonia scabrida
• Murraya paniculata
• Neolitsea sericea
• Ochradenus baccatus
• Perymenium jelskii
• Phenax angustifolius
• Plantago ovata
• Podocarpus sellowii
• Podophyllum pleianthum
• Potentilla candicans
• Primula denticulata
• Prunus mahaleb
• Rhamnus cathartica
• Rhamnus formosana
• Rubus niveus
• Senecio ruwenzoriensis
• Senna didymobotrya
• Solanum nigrum
• Spinacia oleracea
• Spiraea formosana
• Strychnos elaeocarpa
• Strychnos wallichiana
• Teucrium cossonii
• Thujopsis dolabrata
• Tinadendron noumeanum
• Tocoyena formosa
• Trichilia havanensis
• Tripterospermum lanceolatum
• Turnera ulmifolia
• Vachellia leucophloea
• Veronica liwanensis
• Viburnum betulifolium

Cross-Links

• PubChem: 65133
• NPASS: NPC273965
• LOTUS: LTS0166819
• wikiData: Q104918468