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methyl (1R,3R,4S,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,4-dihydroxy-5-[(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 4b3eea00-576c-433d-9f07-30641d3d04e5
Taxonomy Organic oxygen compounds > Organooxygen compounds > Alcohols and polyols > Cyclitols and derivatives > Quinic acids and derivatives
IUPAC Name methyl (1R,3R,4S,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,4-dihydroxy-5-[(E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxycyclohexane-1-carboxylate
SMILES (Canonical) COC1=CC(=CC(=C1O)OC)C=CC(=O)OC2CC(CC(C2O)OC(=O)C=CC3=CC(=C(C=C3)O)O)(C(=O)OC)O
SMILES (Isomeric) COC1=CC(=CC(=C1O)OC)/C=C/C(=O)O[C@@H]2C[C@](C[C@H]([C@@H]2O)OC(=O)/C=C/C3=CC(=C(C=C3)O)O)(C(=O)OC)O
InChI InChI=1S/C28H30O13/c1-37-19-11-16(12-20(38-2)25(19)33)6-9-24(32)41-22-14-28(36,27(35)39-3)13-21(26(22)34)40-23(31)8-5-15-4-7-17(29)18(30)10-15/h4-12,21-22,26,29-30,33-34,36H,13-14H2,1-3H3/b8-5+,9-6+/t21-,22-,26+,28-/m1/s1
InChI Key QXOKQINPRTYYQK-PIHNLQSFSA-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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BDBM50478838
methyl 5-O-caffeoyl-3-O-sinapoylquinate
methyl (1R,3R,4S,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,4-dihydroxy-5-[(E)-3-(4-hydroxy-3,5-dimethoxy-phenyl)prop-2-enoyl]oxy-cyclohexanecarboxylate

2D Structure

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2D Structure of methyl (1R,3R,4S,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,4-dihydroxy-5-[(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 + 0.9693 96.93%
Caco-2 - 0.8705 87.05%
Blood Brain Barrier - 0.6000 60.00%
Human oral bioavailability - 0.7000 70.00%
Subcellular localzation Mitochondria 0.7661 76.61%
OATP2B1 inhibitior - 0.8578 85.78%
OATP1B1 inhibitior + 0.9460 94.60%
OATP1B3 inhibitior + 0.8777 87.77%
MATE1 inhibitior - 0.6800 68.00%
OCT2 inhibitior - 0.8000 80.00%
BSEP inhibitior + 0.7211 72.11%
P-glycoprotein inhibitior + 0.7493 74.93%
P-glycoprotein substrate - 0.6023 60.23%
CYP3A4 substrate + 0.6168 61.68%
CYP2C9 substrate - 0.6044 60.44%
CYP2D6 substrate - 0.8263 82.63%
CYP3A4 inhibition - 0.8713 87.13%
CYP2C9 inhibition - 0.9245 92.45%
CYP2C19 inhibition - 0.9038 90.38%
CYP2D6 inhibition - 0.9519 95.19%
CYP1A2 inhibition - 0.6868 68.68%
CYP2C8 inhibition + 0.6353 63.53%
CYP inhibitory promiscuity - 0.9770 97.70%
UGT catelyzed + 0.9000 90.00%
Carcinogenicity (binary) - 0.8943 89.43%
Carcinogenicity (trinary) Non-required 0.6229 62.29%
Eye corrosion - 0.9921 99.21%
Eye irritation - 0.9185 91.85%
Skin irritation - 0.7930 79.30%
Skin corrosion - 0.9386 93.86%
Ames mutagenesis - 0.7300 73.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6650 66.50%
Micronuclear + 0.5700 57.00%
Hepatotoxicity + 0.5750 57.50%
skin sensitisation - 0.7868 78.68%
Respiratory toxicity + 0.5889 58.89%
Reproductive toxicity + 0.7333 73.33%
Mitochondrial toxicity + 0.5625 56.25%
Nephrotoxicity - 0.9255 92.55%
Acute Oral Toxicity (c) III 0.5830 58.30%
Estrogen receptor binding + 0.7950 79.50%
Androgen receptor binding + 0.7367 73.67%
Thyroid receptor binding + 0.6270 62.70%
Glucocorticoid receptor binding + 0.7541 75.41%
Aromatase binding - 0.5000 50.00%
PPAR gamma + 0.5966 59.66%
Honey bee toxicity - 0.8086 80.86%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity + 0.5300 53.00%
Fish aquatic toxicity + 0.9918 99.18%

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 99.82% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.90% 96.09%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 96.87% 96.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 95.20% 95.56%
CHEMBL1806 P11388 DNA topoisomerase II alpha 92.41% 89.00%
CHEMBL5469 Q14289 Protein tyrosine kinase 2 beta 91.86% 91.03%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 90.59% 85.14%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 89.50% 94.45%
CHEMBL3194 P02766 Transthyretin 89.38% 90.71%
CHEMBL2179 P04062 Beta-glucocerebrosidase 89.10% 85.31%
CHEMBL1293249 Q13887 Kruppel-like factor 5 89.09% 86.33%
CHEMBL4208 P20618 Proteasome component C5 88.28% 90.00%
CHEMBL221 P23219 Cyclooxygenase-1 86.55% 90.17%
CHEMBL3788 O00444 Serine/threonine-protein kinase PLK4 86.46% 83.65%
CHEMBL5608 Q16288 NT-3 growth factor receptor 83.82% 95.89%
CHEMBL2535 P11166 Glucose transporter 83.46% 98.75%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 83.37% 89.62%
CHEMBL340 P08684 Cytochrome P450 3A4 82.67% 91.19%
CHEMBL3713062 P10646 Tissue factor pathway inhibitor 81.14% 97.33%
CHEMBL241 Q14432 Phosphodiesterase 3A 80.99% 92.94%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 80.82% 91.07%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 80.69% 97.14%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 80.51% 92.62%
CHEMBL3137262 O60341 LSD1/CoREST complex 80.25% 97.09%

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 11671431
NPASS NPC163883
LOTUS LTS0141773
wikiData Q105229768