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[(2S,3S,4R,5R)-4-acetyloxy-2-(acetyloxymethyl)-2-[(2R,3R,4S,5S,6R)-6-(acetyloxymethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-5-(hydroxymethyl)oxolan-3-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate

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 415bab76-92d7-44a7-b9d2-3a9ce0575fea
Taxonomy Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acid esters > Coumaric acid esters
IUPAC Name [(2S,3S,4R,5R)-4-acetyloxy-2-(acetyloxymethyl)-2-[(2R,3R,4S,5S,6R)-6-(acetyloxymethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-5-(hydroxymethyl)oxolan-3-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
SMILES (Canonical)
SMILES (Isomeric)
InChI InChI=1S/C27H34O16/c1-13(29)37-11-19-21(34)22(35)23(36)26(40-19)43-27(12-38-14(2)30)25(24(39-15(3)31)18(10-28)42-27)41-20(33)9-6-16-4-7-17(32)8-5-16/h4-9,18-19,21-26,28,32,34-36H,10-12H2,1-3H3/b9-6+/t18-,19-,21-,22+,23-,24-,25+,26-,27+/m1/s1
InChI Key JKZKIQWFVBPCHT-BTUCETIBSA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C27H34O16
Molecular Weight 614.50 g/mol
Exact Mass 614.18468499 g/mol
Topological Polar Surface Area (TPSA) 234.00 Ų
XlogP -1.50
Atomic LogP (AlogP) -1.71
H-Bond Acceptor 16
H-Bond Donor 5
Rotatable Bonds 11

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(2S,3S,4R,5R)-4-acetyloxy-2-(acetyloxymethyl)-2-[(2R,3R,4S,5S,6R)-6-(acetyloxymethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-5-(hydroxymethyl)oxolan-3-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption - 0.7141 71.41%
Caco-2 - 0.8863 88.63%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.8714 87.14%
Subcellular localzation Mitochondria 0.7883 78.83%
OATP2B1 inhibitior - 0.8637 86.37%
OATP1B1 inhibitior + 0.8269 82.69%
OATP1B3 inhibitior + 0.9219 92.19%
MATE1 inhibitior - 0.8800 88.00%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior + 0.9412 94.12%
P-glycoprotein inhibitior + 0.6890 68.90%
P-glycoprotein substrate - 0.7357 73.57%
CYP3A4 substrate + 0.6674 66.74%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8792 87.92%
CYP3A4 inhibition - 0.8472 84.72%
CYP2C9 inhibition - 0.8943 89.43%
CYP2C19 inhibition - 0.9008 90.08%
CYP2D6 inhibition - 0.9359 93.59%
CYP1A2 inhibition - 0.8990 89.90%
CYP2C8 inhibition + 0.7469 74.69%
CYP inhibitory promiscuity - 0.7794 77.94%
UGT catelyzed - 0.8000 80.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.6698 66.98%
Eye corrosion - 0.9910 99.10%
Eye irritation - 0.9317 93.17%
Skin irritation - 0.8186 81.86%
Skin corrosion - 0.9554 95.54%
Ames mutagenesis - 0.6600 66.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4140 41.40%
Micronuclear - 0.6526 65.26%
Hepatotoxicity - 0.8375 83.75%
skin sensitisation - 0.8640 86.40%
Respiratory toxicity - 0.5333 53.33%
Reproductive toxicity + 0.6222 62.22%
Mitochondrial toxicity + 0.5750 57.50%
Nephrotoxicity - 0.6877 68.77%
Acute Oral Toxicity (c) III 0.6006 60.06%
Estrogen receptor binding + 0.8570 85.70%
Androgen receptor binding + 0.6273 62.73%
Thyroid receptor binding - 0.5000 50.00%
Glucocorticoid receptor binding + 0.6751 67.51%
Aromatase binding + 0.5717 57.17%
PPAR gamma + 0.6847 68.47%
Honey bee toxicity - 0.6834 68.34%
Biodegradation - 0.7000 70.00%
Crustacea aquatic toxicity - 0.6700 67.00%
Fish aquatic toxicity + 0.9533 95.33%

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 98.75% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.58% 96.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 94.56% 86.33%
CHEMBL3401 O75469 Pregnane X receptor 94.24% 94.73%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 91.21% 96.00%
CHEMBL4040 P28482 MAP kinase ERK2 90.68% 83.82%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.31% 95.56%
CHEMBL226 P30542 Adenosine A1 receptor 89.14% 95.93%
CHEMBL1806 P11388 DNA topoisomerase II alpha 89.10% 89.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 88.27% 97.09%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 87.78% 85.14%
CHEMBL2581 P07339 Cathepsin D 85.88% 98.95%
CHEMBL3060 Q9Y345 Glycine transporter 2 84.05% 99.17%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 84.01% 94.45%
CHEMBL4208 P20618 Proteasome component C5 83.83% 90.00%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 83.42% 94.62%
CHEMBL1951 P21397 Monoamine oxidase A 82.99% 91.49%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 82.72% 95.50%
CHEMBL5852 Q96P65 Pyroglutamylated RFamide peptide receptor 81.95% 85.00%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 81.78% 86.92%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 81.32% 94.33%
CHEMBL5255 O00206 Toll-like receptor 4 80.88% 92.50%
CHEMBL4481 P35228 Nitric oxide synthase, inducible 80.51% 94.80%
CHEMBL2107 P61073 C-X-C chemokine receptor type 4 80.24% 93.10%
CHEMBL2563 Q9UQL6 Histone deacetylase 5 80.19% 89.67%

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.
Prunus tomentosa

Cross-Links

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PubChem 90676539
NPASS NPC471881
ChEMBL CHEMBL3262769
LOTUS LTS0102837
wikiData Q105130584