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[4-Hydroxy-3-[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyloxy]-5-[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyloxymethyl]-2-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxolan-2-yl]methyl 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 39bb9b22-0aaa-4bec-b980-f1376d519ed1
Taxonomy Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acid esters > Coumaric acid esters
IUPAC Name [4-hydroxy-3-[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyloxy]-5-[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyloxymethyl]-2-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxolan-2-yl]methyl 3-(4-hydroxyphenyl)prop-2-enoate
SMILES (Canonical) COC1=C(C=CC(=C1)C=CC(=O)OCC2C(C(C(O2)(COC(=O)C=CC3=CC=C(C=C3)O)OC4C(C(C(C(O4)CO)O)O)O)OC(=O)C=CC5=CC(=C(C=C5)O)OC)O)O
SMILES (Isomeric) COC1=C(C=CC(=C1)C=CC(=O)OCC2C(C(C(O2)(COC(=O)C=CC3=CC=C(C=C3)O)OC4C(C(C(C(O4)CO)O)O)O)OC(=O)C=CC5=CC(=C(C=C5)O)OC)O)O
InChI InChI=1S/C41H44O19/c1-53-28-17-23(5-12-26(28)44)8-15-32(46)55-20-31-36(50)39(58-34(48)16-9-24-6-13-27(45)29(18-24)54-2)41(59-31,60-40-38(52)37(51)35(49)30(19-42)57-40)21-56-33(47)14-7-22-3-10-25(43)11-4-22/h3-18,30-31,35-40,42-45,49-52H,19-21H2,1-2H3
InChI Key XPMSXAVTDBNKAT-UHFFFAOYSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C41H44O19
Molecular Weight 840.80 g/mol
Exact Mass 840.24767917 g/mol
Topological Polar Surface Area (TPSA) 287.00 Ų
XlogP 1.90
Atomic LogP (AlogP) 0.53
H-Bond Acceptor 19
H-Bond Donor 8
Rotatable Bonds 16

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [4-Hydroxy-3-[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyloxy]-5-[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyloxymethyl]-2-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxolan-2-yl]methyl 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 - 0.7932 79.32%
Caco-2 - 0.8840 88.40%
Blood Brain Barrier - 0.5750 57.50%
Human oral bioavailability - 0.8571 85.71%
Subcellular localzation Mitochondria 0.7226 72.26%
OATP2B1 inhibitior - 0.7214 72.14%
OATP1B1 inhibitior + 0.8492 84.92%
OATP1B3 inhibitior + 0.9557 95.57%
MATE1 inhibitior - 0.8800 88.00%
OCT2 inhibitior - 0.8500 85.00%
BSEP inhibitior + 0.8776 87.76%
P-glycoprotein inhibitior + 0.7341 73.41%
P-glycoprotein substrate - 0.6294 62.94%
CYP3A4 substrate + 0.6678 66.78%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8593 85.93%
CYP3A4 inhibition - 0.7733 77.33%
CYP2C9 inhibition - 0.8269 82.69%
CYP2C19 inhibition - 0.7818 78.18%
CYP2D6 inhibition - 0.9225 92.25%
CYP1A2 inhibition - 0.8862 88.62%
CYP2C8 inhibition + 0.8414 84.14%
CYP inhibitory promiscuity - 0.7325 73.25%
UGT catelyzed + 0.6362 63.62%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.6680 66.80%
Eye corrosion - 0.9901 99.01%
Eye irritation - 0.9124 91.24%
Skin irritation - 0.8527 85.27%
Skin corrosion - 0.9511 95.11%
Ames mutagenesis - 0.7800 78.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7943 79.43%
Micronuclear - 0.5326 53.26%
Hepatotoxicity - 0.9000 90.00%
skin sensitisation - 0.8034 80.34%
Respiratory toxicity - 0.5889 58.89%
Reproductive toxicity + 0.7222 72.22%
Mitochondrial toxicity + 0.5750 57.50%
Nephrotoxicity - 0.8765 87.65%
Acute Oral Toxicity (c) III 0.6640 66.40%
Estrogen receptor binding + 0.8105 81.05%
Androgen receptor binding + 0.7061 70.61%
Thyroid receptor binding + 0.5852 58.52%
Glucocorticoid receptor binding + 0.6754 67.54%
Aromatase binding + 0.5262 52.62%
PPAR gamma + 0.7218 72.18%
Honey bee toxicity - 0.6955 69.55%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity - 0.5800 58.00%
Fish aquatic toxicity + 0.9363 93.63%

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 99.60% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.05% 96.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 97.53% 86.33%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 96.39% 96.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 93.17% 95.56%
CHEMBL3194 P02766 Transthyretin 93.13% 90.71%
CHEMBL1806 P11388 DNA topoisomerase II alpha 92.19% 89.00%
CHEMBL3401 O75469 Pregnane X receptor 91.11% 94.73%
CHEMBL3060 Q9Y345 Glycine transporter 2 90.27% 99.17%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 89.80% 89.62%
CHEMBL3137262 O60341 LSD1/CoREST complex 88.68% 97.09%
CHEMBL4208 P20618 Proteasome component C5 86.12% 90.00%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 85.75% 95.50%
CHEMBL3714130 P46095 G-protein coupled receptor 6 84.66% 97.36%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 83.36% 85.14%
CHEMBL340 P08684 Cytochrome P450 3A4 83.04% 91.19%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 82.78% 94.45%
CHEMBL2563 Q9UQL6 Histone deacetylase 5 81.25% 89.67%
CHEMBL2535 P11166 Glucose transporter 80.89% 98.75%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 80.89% 95.89%
CHEMBL2146302 O94925 Glutaminase kidney isoform, mitochondrial 80.43% 100.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.24% 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.
Smilax bracteata
Smilax china

Cross-Links

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PubChem 85316105
LOTUS LTS0056352
wikiData Q105338854