3-p-Coumaroylquinic acid

Details

• Internal ID: ca975990-5542-44a8-830c-3b4f1ef8f27e
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Alcohols and polyols > Cyclitols and derivatives > Quinic acids and derivatives
• IUPAC Name: (1R,3R,4S,5R)-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-/m1/s1
• InChI Key: BMRSEYFENKXDIS-QHAYPTCMSA-N
• Popularity: 10 references in papers

Physical and Chemical Properties

• 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

• 3-p-Coqa
• 3-O-Coumaroylquinic acid
• 87099-71-6
• 1AF7V9VW0S
• UNII-1AF7V9VW0S
• (1R,3R,4S,5R)-1,3,4-trihydroxy-5-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxycyclohexane-1-carboxylic acid
• o-Coumaroylquinic acid
• 3-O-p-Coumaroylquinic acid
• Cyclohexanecarboxylic acid, 1,3,4-trihydroxy-5-(((2E)-3-(4-hydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-, (1R,3R,4S,5R)-
• (1R,3R,4S,5R)-1,3,4-trihydroxy-5-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-cyclohexane-1-carboxylic acid
• 32451-86-8
• 5-Coumaroyl quinic acid
• p-Coumaroyl 5-O-quinate
• 5-O-p-Coumaroylquinic acid
• SCHEMBL21240786
• CHEBI:75499
• CHEBI:167530
• DTXSID301344004
• AKOS040740142
• NCGC00384821-01
• (1R,3R,4S,5R)-1,3,4-trihydroxy-5-{[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}cyclohexanecarboxylic acid
• 1,4,5-Trihydroxy-3-[[3-(4-hydroxyphenyl)-1-oxo-2-propenyl]oxy]cyclohexanecarboxylic acid, 9CI

2D Structure

ADMET Properties (via admetSAR 2)

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

Proven Targets:

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

• Albizia altissima
• Artocarpus altilis
• Camellia sinensis
• Centaurea solstitialis
• Cosmos diversifolius
• Cryptocarya oblata
• Curcuma caesia
• Cydonia oblonga
• Epaltes mexicana
• Erythrina pallida
• Eucalyptus radiata subsp. radiata
• Hypericum perforatum
• Inga velutina
• Lactuca serriola
• Lagochilus leiacanthus
• Neurolaena lobata
• Ocimum africanum
• Onobrychis viciifolia
• Phelline lucida
• Piptostigma fugax
• Prunus avium
• Prunus cerasus
• Prunus domestica
• Pteris ensiformis
• Pyrus communis
• Rhododendron mucronatum
• Ribes uva-crispa
• Rubus chingii
• Rubus niveus
• Strychnos tricalysioides
• Trichodesma incanum
• Urochloa eminii
• Viburnum dilatatum
• Xanthorrhoea resinosa

Cross-Links

• PubChem: 9945785
• NPASS: NPC254696
• LOTUS: LTS0199226
• wikiData: Q105352163