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methyl (1S,3R,4R,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,5-dihydroxy-4-[(E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxycyclohexane-1-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 eda03085-b9c8-4fd7-937d-51ec94acea68
Taxonomy Organic oxygen compounds > Organooxygen compounds > Alcohols and polyols > Cyclitols and derivatives > Quinic acids and derivatives
IUPAC Name methyl (1S,3R,4R,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,5-dihydroxy-4-[(E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxycyclohexane-1-carboxylate
SMILES (Canonical) COC1=CC(=CC(=C1O)OC)C=CC(=O)OC2C(CC(CC2OC(=O)C=CC3=CC(=C(C=C3)O)O)(C(=O)OC)O)O
SMILES (Isomeric) COC1=CC(=CC(=C1O)OC)/C=C/C(=O)O[C@@H]2[C@@H](C[C@](C[C@H]2OC(=O)/C=C/C3=CC(=C(C=C3)O)O)(C(=O)OC)O)O
InChI InChI=1S/C28H30O13/c1-37-20-11-16(12-21(38-2)25(20)34)6-9-24(33)41-26-19(31)13-28(36,27(35)39-3)14-22(26)40-23(32)8-5-15-4-7-17(29)18(30)10-15/h4-12,19,22,26,29-31,34,36H,13-14H2,1-3H3/b8-5+,9-6+/t19-,22-,26-,28+/m1/s1
InChI Key HNVWFUAOTFONLC-WMUFCWPYSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C28H30O13
Molecular Weight 574.50 g/mol
Exact Mass 574.16864101 g/mol
Topological Polar Surface Area (TPSA) 199.00 Ų
XlogP 2.10
Atomic LogP (AlogP) 1.43
H-Bond Acceptor 13
H-Bond Donor 5
Rotatable Bonds 9

Synonyms

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BDBM50478835
methyl 5-O-caffeoyl-4-O-sinapoylquinate
methyl (1S,3R,4R,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,5-dihydroxy-4-[(E)-3-(4-hydroxy-3,5-dimethoxy-phenyl)prop-2-enoyl]oxy-cyclohexanecarboxylate

2D Structure

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2D Structure of methyl (1S,3R,4R,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,5-dihydroxy-4-[(E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxycyclohexane-1-carboxylate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8663 86.63%
Caco-2 - 0.8699 86.99%
Blood Brain Barrier - 0.6250 62.50%
Human oral bioavailability - 0.6714 67.14%
Subcellular localzation Mitochondria 0.6929 69.29%
OATP2B1 inhibitior - 0.8591 85.91%
OATP1B1 inhibitior + 0.9271 92.71%
OATP1B3 inhibitior + 0.9015 90.15%
MATE1 inhibitior - 0.6800 68.00%
OCT2 inhibitior - 0.8000 80.00%
BSEP inhibitior + 0.9655 96.55%
P-glycoprotein inhibitior + 0.7822 78.22%
P-glycoprotein substrate - 0.5300 53.00%
CYP3A4 substrate + 0.6333 63.33%
CYP2C9 substrate - 0.6044 60.44%
CYP2D6 substrate - 0.8263 82.63%
CYP3A4 inhibition - 0.7527 75.27%
CYP2C9 inhibition - 0.8510 85.10%
CYP2C19 inhibition - 0.8415 84.15%
CYP2D6 inhibition - 0.9007 90.07%
CYP1A2 inhibition - 0.6443 64.43%
CYP2C8 inhibition + 0.5162 51.62%
CYP inhibitory promiscuity - 0.9332 93.32%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.8654 86.54%
Carcinogenicity (trinary) Non-required 0.6440 64.40%
Eye corrosion - 0.9924 99.24%
Eye irritation - 0.9226 92.26%
Skin irritation - 0.7684 76.84%
Skin corrosion - 0.9263 92.63%
Ames mutagenesis - 0.8000 80.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7452 74.52%
Micronuclear + 0.5700 57.00%
Hepatotoxicity + 0.5125 51.25%
skin sensitisation - 0.7905 79.05%
Respiratory toxicity + 0.7111 71.11%
Reproductive toxicity + 0.6778 67.78%
Mitochondrial toxicity + 0.5625 56.25%
Nephrotoxicity - 0.9565 95.65%
Acute Oral Toxicity (c) III 0.5845 58.45%
Estrogen receptor binding + 0.7940 79.40%
Androgen receptor binding + 0.7574 75.74%
Thyroid receptor binding + 0.6441 64.41%
Glucocorticoid receptor binding + 0.7796 77.96%
Aromatase binding - 0.5533 55.33%
PPAR gamma + 0.6762 67.62%
Honey bee toxicity - 0.7981 79.81%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity + 0.5300 53.00%
Fish aquatic toxicity + 0.9890 98.90%

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 99.85% 91.11%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 97.39% 85.14%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.36% 96.09%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 96.72% 96.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 95.24% 95.56%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 93.72% 94.45%
CHEMBL2179 P04062 Beta-glucocerebrosidase 93.10% 85.31%
CHEMBL1806 P11388 DNA topoisomerase II alpha 91.97% 89.00%
CHEMBL4208 P20618 Proteasome component C5 90.99% 90.00%
CHEMBL5469 Q14289 Protein tyrosine kinase 2 beta 90.53% 91.03%
CHEMBL1293249 Q13887 Kruppel-like factor 5 89.74% 86.33%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 87.63% 89.62%
CHEMBL221 P23219 Cyclooxygenase-1 87.21% 90.17%
CHEMBL3194 P02766 Transthyretin 85.89% 90.71%
CHEMBL340 P08684 Cytochrome P450 3A4 85.41% 91.19%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 83.53% 97.14%
CHEMBL3788 O00444 Serine/threonine-protein kinase PLK4 82.35% 83.65%
CHEMBL1821 P08173 Muscarinic acetylcholine receptor M4 82.31% 94.08%
CHEMBL3137262 O60341 LSD1/CoREST complex 81.46% 97.09%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 80.82% 91.07%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 80.73% 99.15%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 80.71% 92.62%
CHEMBL1951 P21397 Monoamine oxidase A 80.27% 91.49%

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.
Gardenia jasminoides

Cross-Links

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PubChem 11635556
NPASS NPC93498
LOTUS LTS0139541
wikiData Q105031089