methyl (2R)-3-(3,4-dihydroxyphenyl)-2-[(E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoyl]oxypropanoate

Details

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Internal ID 41e8732a-c7b8-4e07-a35f-427f102714b3
Taxonomy Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
IUPAC Name methyl (2R)-3-(3,4-dihydroxyphenyl)-2-[(E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoyl]oxypropanoate
SMILES (Canonical) COC1=C(C=C(C=C1)C=CC(=O)OC(CC2=CC(=C(C=C2)O)O)C(=O)OC)O
SMILES (Isomeric) COC1=C(C=C(C=C1)/C=C/C(=O)O[C@H](CC2=CC(=C(C=C2)O)O)C(=O)OC)O
InChI InChI=1S/C20H20O8/c1-26-17-7-4-12(9-16(17)23)5-8-19(24)28-18(20(25)27-2)11-13-3-6-14(21)15(22)10-13/h3-10,18,21-23H,11H2,1-2H3/b8-5+/t18-/m1/s1
InChI Key TUYFFOLCPXHZKL-KRZKXXONSA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C20H20O8
Molecular Weight 388.40 g/mol
Exact Mass 388.11581759 g/mol
Topological Polar Surface Area (TPSA) 123.00 Ų
XlogP 3.00
Atomic LogP (AlogP) 2.15
H-Bond Acceptor 8
H-Bond Donor 3
Rotatable Bonds 7

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of methyl (2R)-3-(3,4-dihydroxyphenyl)-2-[(E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoyl]oxypropanoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8769 87.69%
Caco-2 - 0.5864 58.64%
Blood Brain Barrier - 0.6500 65.00%
Human oral bioavailability - 0.7429 74.29%
Subcellular localzation Mitochondria 0.8459 84.59%
OATP2B1 inhibitior - 0.8576 85.76%
OATP1B1 inhibitior + 0.9342 93.42%
OATP1B3 inhibitior + 0.9214 92.14%
MATE1 inhibitior + 0.6600 66.00%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior + 0.8601 86.01%
P-glycoprotein inhibitior - 0.5507 55.07%
P-glycoprotein substrate - 0.6893 68.93%
CYP3A4 substrate + 0.5552 55.52%
CYP2C9 substrate - 0.7923 79.23%
CYP2D6 substrate - 0.8228 82.28%
CYP3A4 inhibition - 0.6894 68.94%
CYP2C9 inhibition + 0.5000 50.00%
CYP2C19 inhibition - 0.5461 54.61%
CYP2D6 inhibition - 0.7137 71.37%
CYP1A2 inhibition + 0.5410 54.10%
CYP2C8 inhibition + 0.7350 73.50%
CYP inhibitory promiscuity - 0.6462 64.62%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.7747 77.47%
Carcinogenicity (trinary) Non-required 0.6682 66.82%
Eye corrosion - 0.9902 99.02%
Eye irritation - 0.8684 86.84%
Skin irritation - 0.8078 80.78%
Skin corrosion - 0.9472 94.72%
Ames mutagenesis - 0.5800 58.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7406 74.06%
Micronuclear + 0.6559 65.59%
Hepatotoxicity - 0.5750 57.50%
skin sensitisation - 0.8386 83.86%
Respiratory toxicity - 0.5333 53.33%
Reproductive toxicity + 0.5889 58.89%
Mitochondrial toxicity - 0.6375 63.75%
Nephrotoxicity - 0.8517 85.17%
Acute Oral Toxicity (c) III 0.7104 71.04%
Estrogen receptor binding + 0.8698 86.98%
Androgen receptor binding + 0.8018 80.18%
Thyroid receptor binding + 0.5766 57.66%
Glucocorticoid receptor binding + 0.7890 78.90%
Aromatase binding + 0.5490 54.90%
PPAR gamma + 0.5415 54.15%
Honey bee toxicity - 0.7554 75.54%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity + 0.5300 53.00%
Fish aquatic toxicity + 0.9919 99.19%

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 98.98% 91.49%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.40% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.82% 96.09%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 96.31% 96.00%
CHEMBL3060 Q9Y345 Glycine transporter 2 94.81% 99.17%
CHEMBL1293249 Q13887 Kruppel-like factor 5 94.60% 86.33%
CHEMBL1255126 O15151 Protein Mdm4 92.48% 90.20%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.01% 95.56%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 89.31% 94.45%
CHEMBL2581 P07339 Cathepsin D 89.16% 98.95%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 88.55% 95.50%
CHEMBL2535 P11166 Glucose transporter 87.64% 98.75%
CHEMBL3194 P02766 Transthyretin 86.55% 90.71%
CHEMBL1907591 P30926 Neuronal acetylcholine receptor; alpha4/beta4 82.58% 100.00%
CHEMBL4208 P20618 Proteasome component C5 82.20% 90.00%
CHEMBL340 P08684 Cytochrome P450 3A4 80.98% 91.19%
CHEMBL1806 P11388 DNA topoisomerase II alpha 80.73% 89.00%

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.
Glechoma hederacea

Cross-Links

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PubChem 53248747
LOTUS LTS0274549
wikiData Q105265115