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[(2S,3S,4S,5R)-2-[(2R,3R,4S,5S,6R)-6-(acetyloxymethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-3-hydroxy-5-[[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxymethyl]-4-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxyoxolan-2-yl]methyl (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 3dbee8d0-d876-4211-98aa-40b303fc891f
Taxonomy Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acid esters > Coumaric acid esters
IUPAC Name [(2S,3S,4S,5R)-2-[(2R,3R,4S,5S,6R)-6-(acetyloxymethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-3-hydroxy-5-[[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxymethyl]-4-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxyoxolan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
SMILES (Canonical)
SMILES (Isomeric)
InChI InChI=1S/C42H44O19/c1-23(43)55-20-31-36(50)37(51)38(52)41(58-31)61-42(22-57-34(48)16-8-24-3-11-27(44)12-4-24)40(53)39(59-35(49)18-9-25-5-13-28(45)14-6-25)32(60-42)21-56-33(47)17-10-26-7-15-29(46)30(19-26)54-2/h3-19,31-32,36-41,44-46,50-53H,20-22H2,1-2H3/b16-8+,17-10+,18-9+/t31-,32-,36-,37+,38-,39-,40+,41-,42+/m1/s1
InChI Key YWTCWUMCRKCKAD-HFNOVLTQSA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C42H44O19
Molecular Weight 852.80 g/mol
Exact Mass 852.24767917 g/mol
Topological Polar Surface Area (TPSA) 284.00 Ų
XlogP 1.90
Atomic LogP (AlogP) 1.09
H-Bond Acceptor 19
H-Bond Donor 7
Rotatable Bonds 16

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(2S,3S,4S,5R)-2-[(2R,3R,4S,5S,6R)-6-(acetyloxymethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-3-hydroxy-5-[[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxymethyl]-4-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxyoxolan-2-yl]methyl (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 - 0.6410 64.10%
Caco-2 - 0.8819 88.19%
Blood Brain Barrier - 0.6000 60.00%
Human oral bioavailability - 0.8286 82.86%
Subcellular localzation Mitochondria 0.7495 74.95%
OATP2B1 inhibitior - 0.5808 58.08%
OATP1B1 inhibitior + 0.8410 84.10%
OATP1B3 inhibitior + 0.9402 94.02%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.8500 85.00%
BSEP inhibitior + 0.8837 88.37%
P-glycoprotein inhibitior + 0.7415 74.15%
P-glycoprotein substrate - 0.5783 57.83%
CYP3A4 substrate + 0.6857 68.57%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8707 87.07%
CYP3A4 inhibition - 0.8415 84.15%
CYP2C9 inhibition - 0.8086 80.86%
CYP2C19 inhibition - 0.7758 77.58%
CYP2D6 inhibition - 0.9118 91.18%
CYP1A2 inhibition - 0.8528 85.28%
CYP2C8 inhibition + 0.8215 82.15%
CYP inhibitory promiscuity - 0.7530 75.30%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.6832 68.32%
Eye corrosion - 0.9899 98.99%
Eye irritation - 0.9117 91.17%
Skin irritation - 0.8382 83.82%
Skin corrosion - 0.9459 94.59%
Ames mutagenesis - 0.7100 71.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7374 73.74%
Micronuclear - 0.5252 52.52%
Hepatotoxicity - 0.8500 85.00%
skin sensitisation - 0.8066 80.66%
Respiratory toxicity - 0.5222 52.22%
Reproductive toxicity + 0.7111 71.11%
Mitochondrial toxicity + 0.5625 56.25%
Nephrotoxicity - 0.8941 89.41%
Acute Oral Toxicity (c) III 0.6211 62.11%
Estrogen receptor binding + 0.8282 82.82%
Androgen receptor binding + 0.6846 68.46%
Thyroid receptor binding + 0.5843 58.43%
Glucocorticoid receptor binding + 0.6659 66.59%
Aromatase binding + 0.5510 55.10%
PPAR gamma + 0.7392 73.92%
Honey bee toxicity - 0.6789 67.89%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.5000 50.00%
Fish aquatic toxicity + 0.9807 98.07%

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 99.64% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.04% 96.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 97.77% 86.33%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 95.65% 96.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 95.36% 89.00%
CHEMBL1951 P21397 Monoamine oxidase A 94.43% 91.49%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 93.11% 95.56%
CHEMBL3401 O75469 Pregnane X receptor 90.77% 94.73%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 90.25% 89.62%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 89.95% 85.14%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 89.59% 94.45%
CHEMBL3060 Q9Y345 Glycine transporter 2 89.36% 99.17%
CHEMBL3194 P02766 Transthyretin 89.25% 90.71%
CHEMBL4208 P20618 Proteasome component C5 88.52% 90.00%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 85.99% 97.21%
CHEMBL2563 Q9UQL6 Histone deacetylase 5 85.58% 89.67%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 83.92% 95.50%
CHEMBL3137262 O60341 LSD1/CoREST complex 83.59% 97.09%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 83.04% 95.89%
CHEMBL340 P08684 Cytochrome P450 3A4 82.28% 91.19%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 82.24% 96.95%
CHEMBL3922 P50579 Methionine aminopeptidase 2 81.80% 97.28%
CHEMBL2146302 O94925 Glutaminase kidney isoform, mitochondrial 80.10% 100.00%

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.
Smilax bracteata

Cross-Links

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PubChem 162821222
LOTUS LTS0008071
wikiData Q105367281