2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, ethyl ester

Details

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Internal ID 87bd496f-e2cd-4ec3-8c28-0811c9310b54
Taxonomy Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
IUPAC Name ethyl 3-(3,4-dihydroxyphenyl)prop-2-enoate
SMILES (Canonical) CCOC(=O)C=CC1=CC(=C(C=C1)O)O
SMILES (Isomeric) CCOC(=O)C=CC1=CC(=C(C=C1)O)O
InChI InChI=1S/C11H12O4/c1-2-15-11(14)6-4-8-3-5-9(12)10(13)7-8/h3-7,12-13H,2H2,1H3
InChI Key WDKYDMULARNCIS-UHFFFAOYSA-N
Popularity 30 references in papers

Physical and Chemical Properties

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Molecular Formula C11H12O4
Molecular Weight 208.21 g/mol
Exact Mass 208.07355886 g/mol
Topological Polar Surface Area (TPSA) 66.80 Ų
XlogP 2.60
Atomic LogP (AlogP) 1.67
H-Bond Acceptor 4
H-Bond Donor 2
Rotatable Bonds 3

Synonyms

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3-(3,4-Dihydroxy-phenyl)-acrylic acid ethyl ester
WDKYDMULARNCIS-UHFFFAOYSA-N
FT-0641085
FT-0776724
ethyl 3-(3',4'-dihydroxyphenyl)-2-propenoate

2D Structure

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2D Structure of 2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, ethyl ester

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9828 98.28%
Caco-2 + 0.7048 70.48%
Blood Brain Barrier - 0.6000 60.00%
Human oral bioavailability - 0.5571 55.71%
Subcellular localzation Mitochondria 0.9129 91.29%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9588 95.88%
OATP1B3 inhibitior + 0.9746 97.46%
MATE1 inhibitior + 0.5400 54.00%
OCT2 inhibitior - 0.9750 97.50%
BSEP inhibitior - 0.6972 69.72%
P-glycoprotein inhibitior - 0.9901 99.01%
P-glycoprotein substrate - 0.9872 98.72%
CYP3A4 substrate - 0.6079 60.79%
CYP2C9 substrate - 0.7914 79.14%
CYP2D6 substrate - 0.8741 87.41%
CYP3A4 inhibition - 0.9104 91.04%
CYP2C9 inhibition - 0.5692 56.92%
CYP2C19 inhibition - 0.7503 75.03%
CYP2D6 inhibition - 0.9239 92.39%
CYP1A2 inhibition - 0.5610 56.10%
CYP2C8 inhibition + 0.4765 47.65%
CYP inhibitory promiscuity - 0.7118 71.18%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.7270 72.70%
Carcinogenicity (trinary) Non-required 0.6630 66.30%
Eye corrosion - 0.9613 96.13%
Eye irritation + 0.9758 97.58%
Skin irritation + 0.4945 49.45%
Skin corrosion - 0.8907 89.07%
Ames mutagenesis - 0.7800 78.00%
Human Ether-a-go-go-Related Gene inhibition - 0.7182 71.82%
Micronuclear + 0.5788 57.88%
Hepatotoxicity - 0.5822 58.22%
skin sensitisation + 0.6555 65.55%
Respiratory toxicity - 0.8222 82.22%
Reproductive toxicity - 0.5333 53.33%
Mitochondrial toxicity - 0.7875 78.75%
Nephrotoxicity - 0.7569 75.69%
Acute Oral Toxicity (c) III 0.7910 79.10%
Estrogen receptor binding + 0.7547 75.47%
Androgen receptor binding + 0.8179 81.79%
Thyroid receptor binding - 0.6121 61.21%
Glucocorticoid receptor binding - 0.7251 72.51%
Aromatase binding - 0.5556 55.56%
PPAR gamma + 0.5904 59.04%
Honey bee toxicity - 0.9396 93.96%
Biodegradation - 0.5000 50.00%
Crustacea aquatic toxicity - 0.6455 64.55%
Fish aquatic toxicity + 0.9853 98.53%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL1951 P21397 Monoamine oxidase A 97.11% 91.49%
CHEMBL1293249 Q13887 Kruppel-like factor 5 95.51% 86.33%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 94.94% 91.11%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 92.22% 96.00%
CHEMBL3401 O75469 Pregnane X receptor 91.25% 94.73%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 90.87% 95.56%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 90.21% 96.09%
CHEMBL3194 P02766 Transthyretin 87.10% 90.71%
CHEMBL3060 Q9Y345 Glycine transporter 2 86.70% 99.17%
CHEMBL1806 P11388 DNA topoisomerase II alpha 85.22% 89.00%
CHEMBL4208 P20618 Proteasome component C5 83.89% 90.00%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 83.48% 96.95%
CHEMBL2581 P07339 Cathepsin D 83.29% 98.95%
CHEMBL2288 Q13526 Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 82.39% 91.71%
CHEMBL2085 P14174 Macrophage migration inhibitory factor 80.32% 80.78%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.
Achillea nana
Aconitum kongboense
Aconitum napellus
Adenocaulon himalaicum
Angelica ursina
Ardisia macrocarpa
Astragalus bisulcatus
Atractylodes macrocephala
Baccharoides lasiopus
Bidens pilosa
Boenninghausenia albiflora
Bothriocline ripensis
Brachyglottis bidwillii
Bulbophyllum crabro
Calea lantanoides
Cenchrus americanus
Chlorophytum malayense
Chromolaena odorata
Cibotium barometz
Cichorium endivia
Cichorium pumilum
Clausena indica
Coronilla cretica
Cyrtocymura scorpioides
Dioscorea gracillima
Drosera indica
Drummondita hassellii
Dysoxylum densiflorum
Echium rubrum
Empetrum nigrum
Entada africana
Entada polystachya
Ephedra distachya
Ephedra lomatolepis
Euonymus maackii
Flindersia xanthoxyla
Fumaria indica
Galium mollugo
Gardenia imperialis
Gentiana olivieri
Gomesa radicans
Grindelia scorzonerifolia
Helichrysum arenarium
Iberis sempervirens
Incarvillea delavayi
Incarvillea mairei
Ipomoea nil
Isodon eriocalyx
Jateorhiza palmata
Lepidium graminifolium
Lespedeza bicolor
Ligularia nelumbifolia
Ligularia veitchiana
Lindera umbellata
Lonchocarpus atropurpureus
Morus notabilis
Nicotiana gossei
Orthosiphon aristatus var. aristatus
Picradeniopsis oppositifolia
Pinus flexilis
Pinus halepensis
Pinus thunbergii
Plantago major
Plectranthus verticillatus
Pontederia crassipes
Pseuduvaria trimera
Psilotum nudum
Pteris spinescens
Pterocaulon rugosum
Rauvolfia tetraphylla
Roemeria carica
Rydingia limbata
Salvia prionitis
Satureja montana
Saussurea laniceps
Saussurea triangulata
Schumanniophyton magnificum
Senecio grandiflorus
Senegalia mellifera
Smilax china
Solanum campaniforme
Solanum melongena
Solanum nigrum
Stephania succifera
Stevia salicifolia
Tetraria capillaris
Teucrium alyssifolium
Tillandsia recurvata
Tocoyena formosa
Typha latifolia
Uncaria sterrophylla
Vernonanthura serratuloides
Vicia amoena
Vitex limonifolia
Zephyranthes carinata
Ziziphora clinopodioides

Cross-Links

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PubChem 66883
NPASS NPC294555
LOTUS LTS0196241
wikiData Q105302494