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(1R,2S,3S,4R)-2,4-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1-hydroxy-3-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxycyclohexane-1-carboxylic acid

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 96f0c4eb-cbb6-47fc-ba4e-ca929699363a
Taxonomy Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acid esters > Coumaric acid esters
IUPAC Name (1R,2S,3S,4R)-2,4-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1-hydroxy-3-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxycyclohexane-1-carboxylic acid
SMILES (Canonical) C1CC(C(C(C1OC(=O)C=CC2=CC(=C(C=C2)O)O)OC(=O)C=CC3=CC=C(C=C3)O)OC(=O)C=CC4=CC(=C(C=C4)O)O)(C(=O)O)O
SMILES (Isomeric) C1C[C@@]([C@H]([C@H]([C@@H]1OC(=O)/C=C/C2=CC(=C(C=C2)O)O)OC(=O)/C=C/C3=CC=C(C=C3)O)OC(=O)/C=C/C4=CC(=C(C=C4)O)O)(C(=O)O)O
InChI InChI=1S/C34H30O14/c35-22-8-1-19(2-9-22)5-12-29(41)47-31-27(46-28(40)13-6-20-3-10-23(36)25(38)17-20)15-16-34(45,33(43)44)32(31)48-30(42)14-7-21-4-11-24(37)26(39)18-21/h1-14,17-18,27,31-32,35-39,45H,15-16H2,(H,43,44)/b12-5+,13-6+,14-7+/t27-,31+,32+,34-/m1/s1
InChI Key YQNGFWXPPNEWNN-MPLPEFHFSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C34H30O14
Molecular Weight 662.60 g/mol
Exact Mass 662.16355563 g/mol
Topological Polar Surface Area (TPSA) 238.00 Ų
XlogP 3.80
Atomic LogP (AlogP) 3.00
H-Bond Acceptor 13
H-Bond Donor 7
Rotatable Bonds 10

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (1R,2S,3S,4R)-2,4-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1-hydroxy-3-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxycyclohexane-1-carboxylic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9058 90.58%
Caco-2 - 0.9036 90.36%
Blood Brain Barrier - 0.6000 60.00%
Human oral bioavailability - 0.8143 81.43%
Subcellular localzation Mitochondria 0.8302 83.02%
OATP2B1 inhibitior - 0.7109 71.09%
OATP1B1 inhibitior + 0.9318 93.18%
OATP1B3 inhibitior + 0.9533 95.33%
MATE1 inhibitior - 0.6600 66.00%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior + 0.9394 93.94%
P-glycoprotein inhibitior + 0.7564 75.64%
P-glycoprotein substrate - 0.7811 78.11%
CYP3A4 substrate + 0.5984 59.84%
CYP2C9 substrate - 0.5984 59.84%
CYP2D6 substrate - 0.8616 86.16%
CYP3A4 inhibition - 0.8946 89.46%
CYP2C9 inhibition - 0.8358 83.58%
CYP2C19 inhibition - 0.8265 82.65%
CYP2D6 inhibition - 0.9410 94.10%
CYP1A2 inhibition - 0.7828 78.28%
CYP2C8 inhibition + 0.7704 77.04%
CYP inhibitory promiscuity - 0.9740 97.40%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.8154 81.54%
Carcinogenicity (trinary) Non-required 0.5431 54.31%
Eye corrosion - 0.9902 99.02%
Eye irritation - 0.8893 88.93%
Skin irritation - 0.6987 69.87%
Skin corrosion - 0.8675 86.75%
Ames mutagenesis - 0.7100 71.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6997 69.97%
Micronuclear - 0.5041 50.41%
Hepatotoxicity - 0.5575 55.75%
skin sensitisation - 0.6919 69.19%
Respiratory toxicity + 0.6111 61.11%
Reproductive toxicity + 0.6333 63.33%
Mitochondrial toxicity + 0.6250 62.50%
Nephrotoxicity - 0.8273 82.73%
Acute Oral Toxicity (c) III 0.7517 75.17%
Estrogen receptor binding + 0.7782 77.82%
Androgen receptor binding + 0.7852 78.52%
Thyroid receptor binding + 0.5852 58.52%
Glucocorticoid receptor binding + 0.6759 67.59%
Aromatase binding - 0.5989 59.89%
PPAR gamma + 0.6758 67.58%
Honey bee toxicity - 0.8310 83.10%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity - 0.5755 57.55%
Fish aquatic toxicity + 0.9831 98.31%

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 99.62% 91.11%
CHEMBL3194 P02766 Transthyretin 94.23% 90.71%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 93.08% 94.62%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 92.06% 95.56%
CHEMBL1293249 Q13887 Kruppel-like factor 5 91.58% 86.33%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 89.95% 94.45%
CHEMBL1821 P08173 Muscarinic acetylcholine receptor M4 89.85% 94.08%
CHEMBL3137262 O60341 LSD1/CoREST complex 89.25% 97.09%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 88.53% 99.15%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 88.14% 96.09%
CHEMBL245 P20309 Muscarinic acetylcholine receptor M3 87.90% 97.53%
CHEMBL2288 Q13526 Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 87.59% 91.71%
CHEMBL216 P11229 Muscarinic acetylcholine receptor M1 87.50% 94.23%
CHEMBL221 P23219 Cyclooxygenase-1 87.47% 90.17%
CHEMBL340 P08684 Cytochrome P450 3A4 87.29% 91.19%
CHEMBL211 P08172 Muscarinic acetylcholine receptor M2 86.94% 94.97%
CHEMBL206 P03372 Estrogen receptor alpha 83.45% 97.64%
CHEMBL3713062 P10646 Tissue factor pathway inhibitor 82.97% 97.33%
CHEMBL1806 P11388 DNA topoisomerase II alpha 82.86% 89.00%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 81.75% 91.07%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 81.65% 96.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 81.41% 95.89%
CHEMBL1951 P21397 Monoamine oxidase A 81.35% 91.49%
CHEMBL3922 P50579 Methionine aminopeptidase 2 81.23% 97.28%
CHEMBL241 Q14432 Phosphodiesterase 3A 80.55% 92.94%
CHEMBL4208 P20618 Proteasome component C5 80.17% 90.00%

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.
Ipomoea pes-caprae

Cross-Links

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PubChem 163193956
LOTUS LTS0196148
wikiData Q105352348