1,3,4-Tri-O-caffeoylquinic acid

Details

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Internal ID c6f9868e-0d74-422a-a06b-d28e2a514c57
Taxonomy Organic oxygen compounds > Organooxygen compounds > Alcohols and polyols > Cyclitols and derivatives > Quinic acids and derivatives
IUPAC Name (1S,3R,4R,5R)-1,3,4-tris[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-5-hydroxycyclohexane-1-carboxylic acid
SMILES (Canonical) C1C(C(C(CC1(C(=O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)OC(=O)C=CC3=CC(=C(C=C3)O)O)OC(=O)C=CC4=CC(=C(C=C4)O)O)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)O)OC(=O)/C=C/C3=CC(=C(C=C3)O)O)OC(=O)/C=C/C4=CC(=C(C=C4)O)O)O
InChI InChI=1S/C34H30O15/c35-21-7-1-18(13-24(21)38)4-10-29(42)47-28-17-34(33(45)46,49-31(44)12-6-20-3-9-23(37)26(40)15-20)16-27(41)32(28)48-30(43)11-5-19-2-8-22(36)25(39)14-19/h1-15,27-28,32,35-41H,16-17H2,(H,45,46)/b10-4+,11-5+,12-6+/t27-,28-,32-,34+/m1/s1
InChI Key ZDYRXGIWSQSHSO-YOWOTECTSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C34H30O15
Molecular Weight 678.60 g/mol
Exact Mass 678.15847025 g/mol
Topological Polar Surface Area (TPSA) 258.00 Ų
XlogP 3.50
Atomic LogP (AlogP) 2.71
H-Bond Acceptor 14
H-Bond Donor 8
Rotatable Bonds 10

Synonyms

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1,4,5-tri-O-Caffeoylquinic acid

2D Structure

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2D Structure of 1,3,4-Tri-O-caffeoylquinic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9316 93.16%
Caco-2 - 0.8981 89.81%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.6714 67.14%
Subcellular localzation Mitochondria 0.8005 80.05%
OATP2B1 inhibitior - 0.8496 84.96%
OATP1B1 inhibitior + 0.9371 93.71%
OATP1B3 inhibitior + 0.9502 95.02%
MATE1 inhibitior - 0.6800 68.00%
OCT2 inhibitior - 0.8750 87.50%
BSEP inhibitior + 0.8803 88.03%
P-glycoprotein inhibitior + 0.7415 74.15%
P-glycoprotein substrate - 0.8101 81.01%
CYP3A4 substrate + 0.5576 55.76%
CYP2C9 substrate - 0.5931 59.31%
CYP2D6 substrate - 0.8512 85.12%
CYP3A4 inhibition - 0.9109 91.09%
CYP2C9 inhibition - 0.9219 92.19%
CYP2C19 inhibition - 0.8849 88.49%
CYP2D6 inhibition - 0.9442 94.42%
CYP1A2 inhibition - 0.8691 86.91%
CYP2C8 inhibition - 0.6020 60.20%
CYP inhibitory promiscuity - 0.9763 97.63%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.8664 86.64%
Carcinogenicity (trinary) Non-required 0.5584 55.84%
Eye corrosion - 0.9917 99.17%
Eye irritation - 0.8997 89.97%
Skin irritation - 0.7017 70.17%
Skin corrosion - 0.9105 91.05%
Ames mutagenesis - 0.8700 87.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7294 72.94%
Micronuclear + 0.5800 58.00%
Hepatotoxicity + 0.5125 51.25%
skin sensitisation - 0.6487 64.87%
Respiratory toxicity + 0.6889 68.89%
Reproductive toxicity + 0.6778 67.78%
Mitochondrial toxicity + 0.6375 63.75%
Nephrotoxicity - 0.8981 89.81%
Acute Oral Toxicity (c) III 0.7458 74.58%
Estrogen receptor binding + 0.7523 75.23%
Androgen receptor binding + 0.7902 79.02%
Thyroid receptor binding + 0.5677 56.77%
Glucocorticoid receptor binding + 0.6202 62.02%
Aromatase binding - 0.5491 54.91%
PPAR gamma + 0.6386 63.86%
Honey bee toxicity - 0.8215 82.15%
Biodegradation - 0.6750 67.50%
Crustacea aquatic toxicity - 0.6255 62.55%
Fish aquatic toxicity + 0.9945 99.45%

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 99.63% 91.11%
CHEMBL1951 P21397 Monoamine oxidase A 97.92% 91.49%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 94.57% 96.09%
CHEMBL221 P23219 Cyclooxygenase-1 94.14% 90.17%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 93.20% 94.45%
CHEMBL1293249 Q13887 Kruppel-like factor 5 92.71% 86.33%
CHEMBL1821 P08173 Muscarinic acetylcholine receptor M4 90.87% 94.08%
CHEMBL3194 P02766 Transthyretin 90.85% 90.71%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 90.13% 99.15%
CHEMBL4208 P20618 Proteasome component C5 89.95% 90.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 89.80% 89.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.78% 95.56%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 89.44% 96.00%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 88.89% 94.62%
CHEMBL3137262 O60341 LSD1/CoREST complex 84.29% 97.09%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 84.00% 95.50%
CHEMBL340 P08684 Cytochrome P450 3A4 82.93% 91.19%
CHEMBL245 P20309 Muscarinic acetylcholine receptor M3 81.60% 97.53%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 80.97% 91.07%
CHEMBL3475 P05121 Plasminogen activator inhibitor-1 80.87% 83.00%

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.
Arnica montana
Erigeron breviscapus

Cross-Links

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PubChem 10283355
NPASS NPC74142
LOTUS LTS0255207
wikiData Q105372883