4,5-Di-O-caffeoyl-1,3-di-O-coumaroylquinic acid

Details

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Internal ID 1c5cfe70-a486-4faf-9e7f-461a3f9a67a7
Taxonomy Organic acids and derivatives > Carboxylic acids and derivatives > Pentacarboxylic acids and derivatives
IUPAC Name (1S,3R,4R,5R)-3,4-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,5-bis[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy]cyclohexane-1-carboxylic acid
SMILES (Canonical) C1C(C(C(CC1(C(=O)O)OC(=O)C=CC2=CC=C(C=C2)O)OC(=O)C=CC3=CC(=C(C=C3)O)O)OC(=O)C=CC4=CC(=C(C=C4)O)O)OC(=O)C=CC5=CC=C(C=C5)O
SMILES (Isomeric) C1[C@H]([C@H]([C@@H](C[C@@]1(C(=O)O)OC(=O)/C=C/C2=CC=C(C=C2)O)OC(=O)/C=C/C3=CC(=C(C=C3)O)O)OC(=O)/C=C/C4=CC(=C(C=C4)O)O)OC(=O)/C=C/C5=CC=C(C=C5)O
InChI InChI=1S/C43H36O16/c44-29-11-1-25(2-12-29)7-17-37(50)56-35-23-43(42(54)55,59-40(53)20-8-26-3-13-30(45)14-4-26)24-36(57-38(51)18-9-27-5-15-31(46)33(48)21-27)41(35)58-39(52)19-10-28-6-16-32(47)34(49)22-28/h1-22,35-36,41,44-49H,23-24H2,(H,54,55)/b17-7+,18-9+,19-10+,20-8+/t35-,36-,41-,43+/m1/s1
InChI Key NJWGGBNAFGSYNN-XBSZYNOPSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C43H36O16
Molecular Weight 808.70 g/mol
Exact Mass 808.20033506 g/mol
Topological Polar Surface Area (TPSA) 264.00 Ų
XlogP 6.10
Atomic LogP (AlogP) 4.97
H-Bond Acceptor 15
H-Bond Donor 7
Rotatable Bonds 13

Synonyms

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CHEMBL510852
(1S,3R,4R,5R)-3,4-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,5-bis[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy]cyclohexane-1-carboxylic acid

2D Structure

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2D Structure of 4,5-Di-O-caffeoyl-1,3-di-O-coumaroylquinic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9574 95.74%
Caco-2 - 0.8894 88.94%
Blood Brain Barrier - 0.6250 62.50%
Human oral bioavailability - 0.8286 82.86%
Subcellular localzation Mitochondria 0.8543 85.43%
OATP2B1 inhibitior - 0.8523 85.23%
OATP1B1 inhibitior + 0.9333 93.33%
OATP1B3 inhibitior + 0.9417 94.17%
MATE1 inhibitior + 0.5200 52.00%
OCT2 inhibitior - 0.7750 77.50%
BSEP inhibitior + 0.9623 96.23%
P-glycoprotein inhibitior + 0.7729 77.29%
P-glycoprotein substrate - 0.8282 82.82%
CYP3A4 substrate + 0.5710 57.10%
CYP2C9 substrate - 0.5979 59.79%
CYP2D6 substrate - 0.8612 86.12%
CYP3A4 inhibition - 0.9004 90.04%
CYP2C9 inhibition - 0.8767 87.67%
CYP2C19 inhibition - 0.8438 84.38%
CYP2D6 inhibition - 0.9582 95.82%
CYP1A2 inhibition - 0.8286 82.86%
CYP2C8 inhibition + 0.7136 71.36%
CYP inhibitory promiscuity - 0.9642 96.42%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.8630 86.30%
Carcinogenicity (trinary) Non-required 0.5439 54.39%
Eye corrosion - 0.9898 98.98%
Eye irritation - 0.8960 89.60%
Skin irritation - 0.7071 70.71%
Skin corrosion - 0.9249 92.49%
Ames mutagenesis - 0.7800 78.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7768 77.68%
Micronuclear + 0.6000 60.00%
Hepatotoxicity - 0.5130 51.30%
skin sensitisation - 0.5887 58.87%
Respiratory toxicity + 0.6000 60.00%
Reproductive toxicity + 0.5778 57.78%
Mitochondrial toxicity + 0.5125 51.25%
Nephrotoxicity - 0.8217 82.17%
Acute Oral Toxicity (c) III 0.7651 76.51%
Estrogen receptor binding + 0.7601 76.01%
Androgen receptor binding + 0.8166 81.66%
Thyroid receptor binding + 0.5968 59.68%
Glucocorticoid receptor binding + 0.6255 62.55%
Aromatase binding - 0.5333 53.33%
PPAR gamma + 0.6903 69.03%
Honey bee toxicity - 0.8097 80.97%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.5955 59.55%
Fish aquatic toxicity + 0.9963 99.63%

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 99.46% 91.11%
CHEMBL1951 P21397 Monoamine oxidase A 94.87% 91.49%
CHEMBL3194 P02766 Transthyretin 94.70% 90.71%
CHEMBL1293249 Q13887 Kruppel-like factor 5 94.05% 86.33%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 92.92% 96.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 90.21% 95.56%
CHEMBL1821 P08173 Muscarinic acetylcholine receptor M4 89.93% 94.08%
CHEMBL245 P20309 Muscarinic acetylcholine receptor M3 89.89% 97.53%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 89.77% 94.62%
CHEMBL1806 P11388 DNA topoisomerase II alpha 88.42% 89.00%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 88.25% 94.45%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 88.25% 99.15%
CHEMBL211 P08172 Muscarinic acetylcholine receptor M2 87.69% 94.97%
CHEMBL3137262 O60341 LSD1/CoREST complex 86.83% 97.09%
CHEMBL4208 P20618 Proteasome component C5 86.34% 90.00%
CHEMBL340 P08684 Cytochrome P450 3A4 85.31% 91.19%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 84.50% 96.00%
CHEMBL216 P11229 Muscarinic acetylcholine receptor M1 82.97% 94.23%
CHEMBL3060 Q9Y345 Glycine transporter 2 81.69% 99.17%
CHEMBL221 P23219 Cyclooxygenase-1 80.36% 90.17%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 80.33% 95.50%

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 11764287
LOTUS LTS0004760
wikiData Q105180344