3,4-Dicaffeoylquinic acid
| Internal ID | 313259c2-eaed-4449-8a8b-f174b1175efe |
| Taxonomy | Organic oxygen compounds > Organooxygen compounds > Alcohols and polyols > Cyclitols and derivatives > Quinic acids and derivatives |
| IUPAC Name | (1R,3R,4S,5R)-3,4-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,5-dihydroxycyclohexane-1-carboxylic acid |
| SMILES (Canonical) | C1C(C(C(CC1(C(=O)O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)OC(=O)C=CC3=CC(=C(C=C3)O)O)O |
| SMILES (Isomeric) | C1[C@H]([C@@H]([C@@H](C[C@]1(C(=O)O)O)OC(=O)/C=C/C2=CC(=C(C=C2)O)O)OC(=O)/C=C/C3=CC(=C(C=C3)O)O)O |
| InChI | InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(35,24(33)34)11-19(30)23(20)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,35H,11-12H2,(H,33,34)/b7-3+,8-4+/t19-,20-,23+,25-/m1/s1 |
| InChI Key | UFCLZKMFXSILNL-RVXRWRFUSA-N |
| Popularity | 60 references in papers |
| Molecular Formula | C25H24O12 |
| Molecular Weight | 516.40 g/mol |
| Exact Mass | 516.12677620 g/mol |
| Topological Polar Surface Area (TPSA) | 211.00 Ų |
| XlogP | 1.50 |
| Atomic LogP (AlogP) | 1.03 |
| H-Bond Acceptor | 11 |
| H-Bond Donor | 7 |
| Rotatable Bonds | 7 |
| 57378-72-0 |
| 4,5-Dicaffeoylquinic acid |
| 4,5-Di-O-caffeoylquinic acid |
| 3,4-DICQA |
| UNII-E57A0DKE0B |
| E57A0DKE0B |
| 4,5-DCQA |
| CHEMBL177126 |
| 89886-30-6 |
| 3,4-Di-O-Caffeoylquinic acid |
| There are more than 10 synonyms. If you wish to see them all click here. |
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.8460 | 84.60% |
| Caco-2 | - | 0.9181 | 91.81% |
| Blood Brain Barrier | - | 0.5500 | 55.00% |
| Human oral bioavailability | - | 0.6857 | 68.57% |
| Subcellular localzation | Mitochondria | 0.6770 | 67.70% |
| OATP2B1 inhibitior | - | 0.7111 | 71.11% |
| OATP1B1 inhibitior | + | 0.9543 | 95.43% |
| OATP1B3 inhibitior | + | 0.9424 | 94.24% |
| MATE1 inhibitior | - | 0.7400 | 74.00% |
| OCT2 inhibitior | - | 0.8338 | 83.38% |
| BSEP inhibitior | + | 0.8783 | 87.83% |
| P-glycoprotein inhibitior | + | 0.6172 | 61.72% |
| P-glycoprotein substrate | - | 0.8199 | 81.99% |
| CYP3A4 substrate | + | 0.5534 | 55.34% |
| CYP2C9 substrate | - | 0.5941 | 59.41% |
| CYP2D6 substrate | - | 0.8566 | 85.66% |
| CYP3A4 inhibition | - | 0.8744 | 87.44% |
| CYP2C9 inhibition | - | 0.9071 | 90.71% |
| CYP2C19 inhibition | - | 0.9069 | 90.69% |
| CYP2D6 inhibition | - | 0.9388 | 93.88% |
| CYP1A2 inhibition | - | 0.9045 | 90.45% |
| CYP2C8 inhibition | - | 0.6804 | 68.04% |
| CYP inhibitory promiscuity | - | 0.9686 | 96.86% |
| UGT catelyzed | - | 0.5000 | 50.00% |
| Carcinogenicity (binary) | - | 0.8864 | 88.64% |
| Carcinogenicity (trinary) | Non-required | 0.6128 | 61.28% |
| Eye corrosion | - | 0.9932 | 99.32% |
| Eye irritation | - | 0.8935 | 89.35% |
| Skin irritation | - | 0.6985 | 69.85% |
| Skin corrosion | - | 0.9034 | 90.34% |
| Ames mutagenesis | - | 0.9200 | 92.00% |
| Human Ether-a-go-go-Related Gene inhibition | + | 0.7429 | 74.29% |
| Micronuclear | + | 0.5800 | 58.00% |
| Hepatotoxicity | + | 0.7125 | 71.25% |
| skin sensitisation | - | 0.6266 | 62.66% |
| Respiratory toxicity | + | 0.6556 | 65.56% |
| Reproductive toxicity | + | 0.7000 | 70.00% |
| Mitochondrial toxicity | + | 0.6250 | 62.50% |
| Nephrotoxicity | - | 0.8939 | 89.39% |
| Acute Oral Toxicity (c) | III | 0.7775 | 77.75% |
| Estrogen receptor binding | + | 0.7453 | 74.53% |
| Androgen receptor binding | + | 0.7561 | 75.61% |
| Thyroid receptor binding | + | 0.5602 | 56.02% |
| Glucocorticoid receptor binding | + | 0.6464 | 64.64% |
| Aromatase binding | - | 0.5999 | 59.99% |
| PPAR gamma | + | 0.6222 | 62.22% |
| Honey bee toxicity | - | 0.8332 | 83.32% |
| Biodegradation | - | 0.7000 | 70.00% |
| Crustacea aquatic toxicity | - | 0.6055 | 60.55% |
| Fish aquatic toxicity | + | 0.9928 | 99.28% |
Proven Targets:
| CHEMBL ID | UniProt ID | Name | Min activity | Assay type | Source |
|---|---|---|---|---|---|
| CHEMBL5983 | O60218 | Aldo-keto reductase family 1 member B10 |
240 nM |
IC50 |
via Super-PRED
|
| CHEMBL1900 | P15121 | Aldose reductase |
78 nM |
IC50 |
via Super-PRED
|
| CHEMBL2487 | P05067 | Beta amyloid A4 protein |
100 nM 100 nM |
IC50 IC50 |
via Super-PRED
PMID: 22921742 |
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% |
| CHEMBL1951 | P21397 | Monoamine oxidase A | 94.32% | 91.49% |
| CHEMBL221 | P23219 | Cyclooxygenase-1 | 93.56% | 90.17% |
| CHEMBL4203 | Q9HAZ1 | Dual specificity protein kinase CLK4 | 92.96% | 94.45% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 92.27% | 95.56% |
| CHEMBL2035 | P08912 | Muscarinic acetylcholine receptor M5 | 92.17% | 94.62% |
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit | 92.01% | 96.09% |
| CHEMBL1293249 | Q13887 | Kruppel-like factor 5 | 91.22% | 86.33% |
| CHEMBL1821 | P08173 | Muscarinic acetylcholine receptor M4 | 91.06% | 94.08% |
| CHEMBL3194 | P02766 | Transthyretin | 90.55% | 90.71% |
| CHEMBL1860 | P10827 | Thyroid hormone receptor alpha | 89.93% | 99.15% |
| CHEMBL4208 | P20618 | Proteasome component C5 | 89.85% | 90.00% |
| CHEMBL1806 | P11388 | DNA topoisomerase II alpha | 89.60% | 89.00% |
| CHEMBL1075094 | Q16236 | Nuclear factor erythroid 2-related factor 2 | 88.69% | 96.00% |
| CHEMBL2179 | P04062 | Beta-glucocerebrosidase | 88.00% | 85.31% |
| CHEMBL3137262 | O60341 | LSD1/CoREST complex | 84.18% | 97.09% |
| CHEMBL245 | P20309 | Muscarinic acetylcholine receptor M3 | 83.95% | 97.53% |
| CHEMBL340 | P08684 | Cytochrome P450 3A4 | 83.66% | 91.19% |
| CHEMBL3091268 | Q92753 | Nuclear receptor ROR-beta | 82.42% | 95.50% |
| CHEMBL216 | P11229 | Muscarinic acetylcholine receptor M1 | 81.79% | 94.23% |
| CHEMBL211 | P08172 | Muscarinic acetylcholine receptor M2 | 80.31% | 94.97% |
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.
To see more specific details click the taxa you are interested in.
| PubChem | 6474309 |
| NPASS | NPC206095 |
| ChEMBL | CHEMBL177126 |
| LOTUS | LTS0134972 |
| wikiData | Q27276885 |