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methyl (1S,2R,3R,5S,7R)-7-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxymethyl]-2-hydroxy-3-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy-6,8-dioxabicyclo[3.2.1]octane-5-carboxylate

Table of Contents

Details
Physical and Chemical Properties
Synonyms
2D Structure
3D Structure
ADMET Properties
Targets (proven and/or predicted)
Plants that contains it
Cross-Links

Details

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Internal ID bf35d097-665a-453d-9176-38a47e7284e4
Taxonomy Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
IUPAC Name methyl (1S,2R,3R,5S,7R)-7-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxymethyl]-2-hydroxy-3-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy-6,8-dioxabicyclo[3.2.1]octane-5-carboxylate
SMILES (Canonical) COC1=C(C=CC(=C1)C=CC(=O)OC2CC3(OC(C(C2O)O3)COC(=O)C=CC4=CC(=C(C=C4)O)O)C(=O)OC)O
SMILES (Isomeric) COC1=C(C=CC(=C1)/C=C/C(=O)O[C@@H]2C[C@@]3(O[C@@H]([C@H]([C@@H]2O)O3)COC(=O)/C=C/C4=CC(=C(C=C4)O)O)C(=O)OC)O
InChI InChI=1S/C28H28O13/c1-36-20-12-16(4-8-18(20)30)6-10-24(33)39-21-13-28(27(35)37-2)40-22(26(41-28)25(21)34)14-38-23(32)9-5-15-3-7-17(29)19(31)11-15/h3-12,21-22,25-26,29-31,34H,13-14H2,1-2H3/b9-5+,10-6+/t21-,22-,25-,26-,28+/m1/s1
InChI Key YEMWKQFIGUCZFS-PBYGLRBLSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C28H28O13
Molecular Weight 572.50 g/mol
Exact Mass 572.15299094 g/mol
Topological Polar Surface Area (TPSA) 188.00 Ų
XlogP 2.10
Atomic LogP (AlogP) 1.41
H-Bond Acceptor 13
H-Bond Donor 4
Rotatable Bonds 9

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of methyl (1S,2R,3R,5S,7R)-7-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxymethyl]-2-hydroxy-3-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy-6,8-dioxabicyclo[3.2.1]octane-5-carboxylate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.5530 55.30%
Caco-2 - 0.8649 86.49%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.7714 77.14%
Subcellular localzation Mitochondria 0.7952 79.52%
OATP2B1 inhibitior - 0.8605 86.05%
OATP1B1 inhibitior + 0.9065 90.65%
OATP1B3 inhibitior + 0.8925 89.25%
MATE1 inhibitior - 0.7000 70.00%
OCT2 inhibitior - 0.7500 75.00%
BSEP inhibitior + 0.9448 94.48%
P-glycoprotein inhibitior + 0.7527 75.27%
P-glycoprotein substrate - 0.5763 57.63%
CYP3A4 substrate + 0.6571 65.71%
CYP2C9 substrate - 0.8028 80.28%
CYP2D6 substrate - 0.8407 84.07%
CYP3A4 inhibition - 0.7661 76.61%
CYP2C9 inhibition - 0.7088 70.88%
CYP2C19 inhibition - 0.6104 61.04%
CYP2D6 inhibition - 0.9130 91.30%
CYP1A2 inhibition - 0.8156 81.56%
CYP2C8 inhibition + 0.7246 72.46%
CYP inhibitory promiscuity - 0.8266 82.66%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9600 96.00%
Carcinogenicity (trinary) Non-required 0.6105 61.05%
Eye corrosion - 0.9895 98.95%
Eye irritation - 0.9281 92.81%
Skin irritation - 0.8224 82.24%
Skin corrosion - 0.9440 94.40%
Ames mutagenesis - 0.7100 71.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4089 40.89%
Micronuclear + 0.5559 55.59%
Hepatotoxicity - 0.6125 61.25%
skin sensitisation - 0.7987 79.87%
Respiratory toxicity + 0.6111 61.11%
Reproductive toxicity + 0.8444 84.44%
Mitochondrial toxicity + 0.7000 70.00%
Nephrotoxicity - 0.9171 91.71%
Acute Oral Toxicity (c) III 0.3873 38.73%
Estrogen receptor binding + 0.8430 84.30%
Androgen receptor binding + 0.7717 77.17%
Thyroid receptor binding + 0.6456 64.56%
Glucocorticoid receptor binding + 0.7980 79.80%
Aromatase binding + 0.5191 51.91%
PPAR gamma + 0.6886 68.86%
Honey bee toxicity - 0.7720 77.20%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity + 0.5400 54.00%
Fish aquatic toxicity + 0.9809 98.09%

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
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 99.90% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.98% 96.09%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 96.99% 96.00%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 94.23% 85.14%
CHEMBL1293249 Q13887 Kruppel-like factor 5 93.94% 86.33%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 92.28% 95.56%
CHEMBL1951 P21397 Monoamine oxidase A 90.72% 91.49%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 89.94% 94.45%
CHEMBL1806 P11388 DNA topoisomerase II alpha 89.27% 89.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 87.54% 97.09%
CHEMBL3060 Q9Y345 Glycine transporter 2 86.89% 99.17%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 86.04% 92.62%
CHEMBL3401 O75469 Pregnane X receptor 85.99% 94.73%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 85.84% 89.62%
CHEMBL2535 P11166 Glucose transporter 85.10% 98.75%
CHEMBL5608 Q16288 NT-3 growth factor receptor 83.69% 95.89%
CHEMBL3194 P02766 Transthyretin 83.60% 90.71%
CHEMBL221 P23219 Cyclooxygenase-1 83.47% 90.17%
CHEMBL4208 P20618 Proteasome component C5 82.69% 90.00%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 81.31% 97.14%
CHEMBL5469 Q14289 Protein tyrosine kinase 2 beta 81.14% 91.03%
CHEMBL340 P08684 Cytochrome P450 3A4 80.52% 91.19%

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.
Erigeron canadensis

Cross-Links

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PubChem 46184565
NPASS NPC44730
LOTUS LTS0141191
wikiData Q105347313