Dicaffeoyl quinic acid

Details

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Internal ID bb46c978-97b7-4766-9ad2-a6b77b481c9e
Taxonomy Organic oxygen compounds > Organooxygen compounds > Alcohols and polyols > Cyclitols and derivatives > Quinic acids and derivatives
IUPAC Name 3,5-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,4-dihydroxycyclohexane-1-carboxylic acid
SMILES (Canonical) C1C(C(C(CC1(C(=O)O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)O)OC(=O)C=CC3=CC(=C(C=C3)O)O
SMILES (Isomeric) C1C(CC(C(C1OC(=O)/C=C/C2=CC(=C(C=C2)O)O)O)OC(=O)/C=C/C3=CC(=C(C=C3)O)O)(O)C(=O)O
InChI InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(30)36-19-11-25(35,24(33)34)12-20(23(19)32)37-22(31)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-29,32,35H,11-12H2,(H,33,34)/b7-3+,8-4+
InChI Key KRZBCHWVBQOTNZ-FCXRPNKRSA-N
Popularity 2 references in papers

Physical and Chemical Properties

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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

Synonyms

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Dicaffeoyl quinic acid
3,5-Dicaffeoyl-epi-quinic acid
879305-14-3
SCHEMBL12410527
SCHEMBL23987356
KRZBCHWVBQOTNZ-FCXRPNKRSA-N
EX-A4055
BDBM50528375
PD012056
3,5-Bis[(3,4-dihydroxy-trans-cinnamoyl)oxy]-1,4-dihydroxy-1-cyclohexanecarboxylic acid
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of Dicaffeoyl quinic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9651 96.51%
Caco-2 - 0.9069 90.69%
Blood Brain Barrier - 0.5750 57.50%
Human oral bioavailability - 0.7000 70.00%
Subcellular localzation Mitochondria 0.8118 81.18%
OATP2B1 inhibitior - 0.7089 70.89%
OATP1B1 inhibitior + 0.9692 96.92%
OATP1B3 inhibitior + 0.9391 93.91%
MATE1 inhibitior - 0.7400 74.00%
OCT2 inhibitior - 0.8250 82.50%
BSEP inhibitior + 0.7868 78.68%
P-glycoprotein inhibitior + 0.6229 62.29%
P-glycoprotein substrate - 0.8808 88.08%
CYP3A4 substrate + 0.5281 52.81%
CYP2C9 substrate - 0.5941 59.41%
CYP2D6 substrate - 0.8566 85.66%
CYP3A4 inhibition - 0.9206 92.06%
CYP2C9 inhibition - 0.9236 92.36%
CYP2C19 inhibition - 0.8975 89.75%
CYP2D6 inhibition - 0.9548 95.48%
CYP1A2 inhibition - 0.8878 88.78%
CYP2C8 inhibition + 0.4547 45.47%
CYP inhibitory promiscuity - 0.9803 98.03%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.8764 87.64%
Carcinogenicity (trinary) Non-required 0.5620 56.20%
Eye corrosion - 0.9907 99.07%
Eye irritation - 0.8916 89.16%
Skin irritation - 0.7018 70.18%
Skin corrosion - 0.9182 91.82%
Ames mutagenesis - 0.9000 90.00%
Human Ether-a-go-go-Related Gene inhibition - 0.3888 38.88%
Micronuclear + 0.6100 61.00%
Hepatotoxicity + 0.7431 74.31%
skin sensitisation - 0.5835 58.35%
Respiratory toxicity + 0.5556 55.56%
Reproductive toxicity + 0.6667 66.67%
Mitochondrial toxicity + 0.6125 61.25%
Nephrotoxicity - 0.8184 81.84%
Acute Oral Toxicity (c) III 0.7686 76.86%
Estrogen receptor binding + 0.7607 76.07%
Androgen receptor binding + 0.7363 73.63%
Thyroid receptor binding + 0.5658 56.58%
Glucocorticoid receptor binding + 0.6811 68.11%
Aromatase binding - 0.5534 55.34%
PPAR gamma + 0.6232 62.32%
Honey bee toxicity - 0.8390 83.90%
Biodegradation - 0.7000 70.00%
Crustacea aquatic toxicity - 0.6155 61.55%
Fish aquatic toxicity + 0.9943 99.43%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
CHEMBL5983 O60218 Aldo-keto reductase family 1 member B10 130 nM
IC50
via Super-PRED
CHEMBL1900 P15121 Aldose reductase 88 nM
IC50
via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 99.64% 91.11%
CHEMBL1951 P21397 Monoamine oxidase A 93.87% 91.49%
CHEMBL221 P23219 Cyclooxygenase-1 93.20% 90.17%
CHEMBL3194 P02766 Transthyretin 92.98% 90.71%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 92.21% 95.56%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 91.37% 94.62%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 90.74% 96.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 90.65% 86.33%
CHEMBL1806 P11388 DNA topoisomerase II alpha 90.15% 89.00%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 89.15% 96.00%
CHEMBL1821 P08173 Muscarinic acetylcholine receptor M4 88.90% 94.08%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 88.29% 94.45%
CHEMBL245 P20309 Muscarinic acetylcholine receptor M3 88.14% 97.53%
CHEMBL4208 P20618 Proteasome component C5 86.85% 90.00%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 85.21% 99.15%
CHEMBL216 P11229 Muscarinic acetylcholine receptor M1 84.88% 94.23%
CHEMBL3137262 O60341 LSD1/CoREST complex 83.11% 97.09%
CHEMBL2179 P04062 Beta-glucocerebrosidase 81.62% 85.31%
CHEMBL211 P08172 Muscarinic acetylcholine receptor M2 80.93% 94.97%
CHEMBL340 P08684 Cytochrome P450 3A4 80.67% 91.19%

Cross-Links

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PubChem 13604687
NPASS NPC24146
LOTUS LTS0032454
wikiData Q105145297