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[(2S,3S,4R,5R)-2-[(2R,3R,4R,5S,6R)-5-acetyloxy-6-(acetyloxymethyl)-3,4-dihydroxyoxan-2-yl]oxy-2-(acetyloxymethyl)-4-hydroxy-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 287c437b-b4d5-4500-8cd9-4790aab30c72
Taxonomy Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acid esters > Coumaric acid esters
IUPAC Name [(2S,3S,4R,5R)-2-[(2R,3R,4R,5S,6R)-5-acetyloxy-6-(acetyloxymethyl)-3,4-dihydroxyoxan-2-yl]oxy-2-(acetyloxymethyl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
SMILES (Canonical)
SMILES (Isomeric)
InChI InChI=1S/C27H34O16/c1-13(29)37-11-19-24(39-15(3)31)22(35)23(36)26(40-19)43-27(12-38-14(2)30)25(21(34)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 RXPCAYUGVCVMEX-FWAKUVGUSA-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 -1.00
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)-2-[(2R,3R,4R,5S,6R)-5-acetyloxy-6-(acetyloxymethyl)-3,4-dihydroxyoxan-2-yl]oxy-2-(acetyloxymethyl)-4-hydroxy-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 - 0.8763 87.63%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.9000 90.00%
Subcellular localzation Mitochondria 0.7883 78.83%
OATP2B1 inhibitior - 0.8614 86.14%
OATP1B1 inhibitior + 0.8444 84.44%
OATP1B3 inhibitior + 0.9219 92.19%
MATE1 inhibitior - 0.8800 88.00%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior + 0.8499 84.99%
P-glycoprotein inhibitior + 0.6435 64.35%
P-glycoprotein substrate - 0.6825 68.25%
CYP3A4 substrate + 0.6657 66.57%
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 + 0.7219 72.19%
CYP inhibitory promiscuity - 0.7794 77.94%
UGT catelyzed - 0.7000 70.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.6698 66.98%
Eye corrosion - 0.9910 99.10%
Eye irritation - 0.9242 92.42%
Skin irritation - 0.8186 81.86%
Skin corrosion - 0.9554 95.54%
Ames mutagenesis - 0.6000 60.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4146 41.46%
Micronuclear - 0.6526 65.26%
Hepatotoxicity - 0.8375 83.75%
skin sensitisation - 0.8640 86.40%
Respiratory toxicity - 0.5889 58.89%
Reproductive toxicity + 0.6222 62.22%
Mitochondrial toxicity + 0.5750 57.50%
Nephrotoxicity - 0.5951 59.51%
Acute Oral Toxicity (c) III 0.6006 60.06%
Estrogen receptor binding + 0.8326 83.26%
Androgen receptor binding + 0.6432 64.32%
Thyroid receptor binding + 0.5209 52.09%
Glucocorticoid receptor binding + 0.5783 57.83%
Aromatase binding + 0.6068 60.68%
PPAR gamma + 0.6918 69.18%
Honey bee toxicity - 0.6764 67.64%
Biodegradation - 0.7250 72.50%
Crustacea aquatic toxicity - 0.6400 64.00%
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 98.23% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.92% 96.09%
CHEMBL3401 O75469 Pregnane X receptor 93.73% 94.73%
CHEMBL1293249 Q13887 Kruppel-like factor 5 93.20% 86.33%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 91.10% 96.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 89.24% 89.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 88.79% 95.56%
CHEMBL4481 P35228 Nitric oxide synthase, inducible 86.48% 94.80%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 86.43% 94.45%
CHEMBL3137262 O60341 LSD1/CoREST complex 85.74% 97.09%
CHEMBL2581 P07339 Cathepsin D 84.88% 98.95%
CHEMBL2107 P61073 C-X-C chemokine receptor type 4 84.72% 93.10%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 84.66% 85.14%
CHEMBL3060 Q9Y345 Glycine transporter 2 84.56% 99.17%
CHEMBL226 P30542 Adenosine A1 receptor 83.27% 95.93%
CHEMBL340 P08684 Cytochrome P450 3A4 83.22% 91.19%
CHEMBL2563 Q9UQL6 Histone deacetylase 5 83.15% 89.67%
CHEMBL4208 P20618 Proteasome component C5 82.98% 90.00%
CHEMBL5852 Q96P65 Pyroglutamylated RFamide peptide receptor 82.92% 85.00%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 82.03% 86.92%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 80.52% 95.89%
CHEMBL3922 P50579 Methionine aminopeptidase 2 80.32% 97.28%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 80.31% 94.33%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.25% 95.89%

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 90676540
NPASS NPC471882
ChEMBL CHEMBL3262770
LOTUS LTS0034619
wikiData Q105247206