3-Caffeoyl-4-sinapoylquinic acid

Details

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Internal ID d24f9070-d36c-4177-93b6-18d64a671ae0
Taxonomy Organic oxygen compounds > Organooxygen compounds > Alcohols and polyols > Cyclitols and derivatives > Quinic acids and derivatives
IUPAC Name (1S,3S,4S,5S)-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-carboxylic acid
SMILES (Canonical) COC1=CC(=CC(=C1O)OC)C=CC(=O)OC2C(CC(CC2OC(=O)C=CC3=CC(=C(C=C3)O)O)(C(=O)O)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)O)O)O
InChI InChI=1S/C27H28O13/c1-37-19-10-15(11-20(38-2)24(19)33)5-8-23(32)40-25-18(30)12-27(36,26(34)35)13-21(25)39-22(31)7-4-14-3-6-16(28)17(29)9-14/h3-11,18,21,25,28-30,33,36H,12-13H2,1-2H3,(H,34,35)/b7-4+,8-5+/t18-,21-,25-,27-/m0/s1
InChI Key BEDSGEULUAVXQH-UEMFYZCUSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C27H28O13
Molecular Weight 560.50 g/mol
Exact Mass 560.15299094 g/mol
Topological Polar Surface Area (TPSA) 210.00 Ų
XlogP 1.80
Atomic LogP (AlogP) 1.34
H-Bond Acceptor 12
H-Bond Donor 6
Rotatable Bonds 9

Synonyms

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3-Caffeoyl-4-sinapoylquinic acid
110241-35-5
Cyclohexanecarboxylic acid, 3-((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-1,5-dihydroxy-4-((3-(4-hydroxy-3,5-dimethoxyphenyl)-1-oxo-2-propenyl)oxy)-, (1S-(1alpha,3beta(E),4alpha(E),5alpha))-
(1S,3S,4S,5S)-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-carboxylic acid
BEDSGEULUAVXQH-UEMFYZCUSA-N
C27H28O13
C27-H28-O13

2D Structure

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2D Structure of 3-Caffeoyl-4-sinapoylquinic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8826 88.26%
Caco-2 - 0.8853 88.53%
Blood Brain Barrier - 0.6000 60.00%
Human oral bioavailability - 0.6714 67.14%
Subcellular localzation Mitochondria 0.6955 69.55%
OATP2B1 inhibitior - 0.7143 71.43%
OATP1B1 inhibitior + 0.9246 92.46%
OATP1B3 inhibitior + 0.9377 93.77%
MATE1 inhibitior - 0.8000 80.00%
OCT2 inhibitior - 0.8088 80.88%
BSEP inhibitior + 0.8865 88.65%
P-glycoprotein inhibitior + 0.7223 72.23%
P-glycoprotein substrate - 0.5850 58.50%
CYP3A4 substrate + 0.6240 62.40%
CYP2C9 substrate + 0.6014 60.14%
CYP2D6 substrate - 0.8439 84.39%
CYP3A4 inhibition - 0.8581 85.81%
CYP2C9 inhibition - 0.8805 88.05%
CYP2C19 inhibition - 0.8804 88.04%
CYP2D6 inhibition - 0.9038 90.38%
CYP1A2 inhibition - 0.7465 74.65%
CYP2C8 inhibition + 0.5251 52.51%
CYP inhibitory promiscuity - 0.9641 96.41%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9064 90.64%
Carcinogenicity (trinary) Non-required 0.6679 66.79%
Eye corrosion - 0.9917 99.17%
Eye irritation - 0.9243 92.43%
Skin irritation - 0.7480 74.80%
Skin corrosion - 0.8855 88.55%
Ames mutagenesis - 0.8800 88.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7730 77.30%
Micronuclear + 0.5700 57.00%
Hepatotoxicity + 0.5625 56.25%
skin sensitisation - 0.7936 79.36%
Respiratory toxicity + 0.7333 73.33%
Reproductive toxicity + 0.7667 76.67%
Mitochondrial toxicity + 0.6000 60.00%
Nephrotoxicity - 0.9309 93.09%
Acute Oral Toxicity (c) III 0.6508 65.08%
Estrogen receptor binding + 0.7131 71.31%
Androgen receptor binding + 0.7360 73.60%
Thyroid receptor binding + 0.5878 58.78%
Glucocorticoid receptor binding + 0.7444 74.44%
Aromatase binding - 0.5323 53.23%
PPAR gamma + 0.6048 60.48%
Honey bee toxicity - 0.8219 82.19%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.5355 53.55%
Fish aquatic toxicity + 0.9892 98.92%

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 99.69% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.28% 96.09%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 96.51% 96.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 96.18% 95.56%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 93.91% 85.14%
CHEMBL1293249 Q13887 Kruppel-like factor 5 93.84% 86.33%
CHEMBL1806 P11388 DNA topoisomerase II alpha 92.94% 89.00%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 92.78% 94.45%
CHEMBL1821 P08173 Muscarinic acetylcholine receptor M4 92.57% 94.08%
CHEMBL3194 P02766 Transthyretin 90.73% 90.71%
CHEMBL221 P23219 Cyclooxygenase-1 90.47% 90.17%
CHEMBL4208 P20618 Proteasome component C5 89.69% 90.00%
CHEMBL340 P08684 Cytochrome P450 3A4 87.18% 91.19%
CHEMBL2179 P04062 Beta-glucocerebrosidase 86.91% 85.31%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 85.89% 99.15%
CHEMBL1951 P21397 Monoamine oxidase A 84.45% 91.49%
CHEMBL5469 Q14289 Protein tyrosine kinase 2 beta 84.22% 91.03%
CHEMBL241 Q14432 Phosphodiesterase 3A 84.00% 92.94%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 81.08% 89.62%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 80.08% 97.14%

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.
Phoenix dactylifera

Cross-Links

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PubChem 6450024
NPASS NPC124837