3-O-p-Coumaroylquinic acid

Details

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Internal ID 2f24a2b2-84cd-4cde-9d3c-dd0458001e9f
Taxonomy Organic oxygen compounds > Organooxygen compounds > Alcohols and polyols > Cyclitols and derivatives > Quinic acids and derivatives
IUPAC Name (1R,3S,4S,5S)-1,3,4-trihydroxy-5-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxycyclohexane-1-carboxylic acid
SMILES (Canonical) C1C(C(C(CC1(C(=O)O)O)OC(=O)C=CC2=CC=C(C=C2)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)O
InChI InChI=1S/C16H18O8/c17-10-4-1-9(2-5-10)3-6-13(19)24-12-8-16(23,15(21)22)7-11(18)14(12)20/h1-6,11-12,14,17-18,20,23H,7-8H2,(H,21,22)/b6-3+/t11-,12-,14-,16+/m0/s1
InChI Key BMRSEYFENKXDIS-LUTKEZBSSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C16H18O8
Molecular Weight 338.31 g/mol
Exact Mass 338.10016753 g/mol
Topological Polar Surface Area (TPSA) 145.00 Ų
XlogP -0.10
Atomic LogP (AlogP) -0.35
H-Bond Acceptor 7
H-Bond Donor 5
Rotatable Bonds 4

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of 3-O-p-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 + 0.8214 82.14%
Caco-2 - 0.9187 91.87%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.8143 81.43%
Subcellular localzation Mitochondria 0.7282 72.82%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9415 94.15%
OATP1B3 inhibitior + 0.9480 94.80%
MATE1 inhibitior - 0.8600 86.00%
OCT2 inhibitior - 0.8588 85.88%
BSEP inhibitior - 0.8109 81.09%
P-glycoprotein inhibitior - 0.9360 93.60%
P-glycoprotein substrate - 0.7896 78.96%
CYP3A4 substrate + 0.5647 56.47%
CYP2C9 substrate + 0.6015 60.15%
CYP2D6 substrate - 0.8566 85.66%
CYP3A4 inhibition - 0.8904 89.04%
CYP2C9 inhibition - 0.9285 92.85%
CYP2C19 inhibition - 0.9200 92.00%
CYP2D6 inhibition - 0.9505 95.05%
CYP1A2 inhibition - 0.9417 94.17%
CYP2C8 inhibition + 0.5190 51.90%
CYP inhibitory promiscuity - 0.9725 97.25%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9064 90.64%
Carcinogenicity (trinary) Non-required 0.5943 59.43%
Eye corrosion - 0.9912 99.12%
Eye irritation - 0.8815 88.15%
Skin irritation - 0.6545 65.45%
Skin corrosion - 0.9044 90.44%
Ames mutagenesis - 0.8700 87.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5753 57.53%
Micronuclear + 0.5800 58.00%
Hepatotoxicity + 0.6243 62.43%
skin sensitisation - 0.6336 63.36%
Respiratory toxicity + 0.5556 55.56%
Reproductive toxicity + 0.6222 62.22%
Mitochondrial toxicity + 0.5250 52.50%
Nephrotoxicity - 0.7184 71.84%
Acute Oral Toxicity (c) III 0.7858 78.58%
Estrogen receptor binding + 0.6827 68.27%
Androgen receptor binding + 0.5784 57.84%
Thyroid receptor binding + 0.5245 52.45%
Glucocorticoid receptor binding + 0.7052 70.52%
Aromatase binding - 0.4852 48.52%
PPAR gamma - 0.5114 51.14%
Honey bee toxicity - 0.8451 84.51%
Biodegradation - 0.6750 67.50%
Crustacea aquatic toxicity - 0.6255 62.55%
Fish aquatic toxicity + 0.9790 97.90%

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 98.02% 91.11%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 92.55% 94.62%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 92.53% 96.09%
CHEMBL216 P11229 Muscarinic acetylcholine receptor M1 92.43% 94.23%
CHEMBL211 P08172 Muscarinic acetylcholine receptor M2 92.09% 94.97%
CHEMBL1821 P08173 Muscarinic acetylcholine receptor M4 91.63% 94.08%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.39% 95.56%
CHEMBL245 P20309 Muscarinic acetylcholine receptor M3 91.22% 97.53%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 90.01% 94.45%
CHEMBL2179 P04062 Beta-glucocerebrosidase 88.85% 85.31%
CHEMBL3194 P02766 Transthyretin 88.39% 90.71%
CHEMBL1293249 Q13887 Kruppel-like factor 5 87.81% 86.33%
CHEMBL3137262 O60341 LSD1/CoREST complex 87.57% 97.09%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 87.43% 96.00%
CHEMBL221 P23219 Cyclooxygenase-1 87.18% 90.17%
CHEMBL1806 P11388 DNA topoisomerase II alpha 86.35% 89.00%
CHEMBL4208 P20618 Proteasome component C5 83.63% 90.00%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 81.09% 95.89%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 81.00% 95.50%
CHEMBL2288 Q13526 Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 80.65% 91.71%

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.
Citrus medica
Eucalyptus globulus
Lonicera japonica
Saussurea involucrata

Cross-Links

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PubChem 14158103
NPASS NPC194665
LOTUS LTS0270006
wikiData Q104938513