4,5-Dicaffeoylquinic acid

Details

• Internal ID: 3d2a69d8-1417-4c83-8620-648693b6f2cc
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Alcohols and polyols > Cyclitols and derivatives > Quinic acids and derivatives
• IUPAC Name: (1S,3R,4R,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-PSEXTPKNSA-N
• Popularity: 149 references in papers

Physical and Chemical Properties

• 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

• Isochlorogenic acid b
• 14534-61-3
• 4,5-Dicqa
• 4,5-Dicaffeoylquinic acid
• (1S,3R,4R,5R)-3,4-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,5-dihydroxycyclohexane-1-carboxylic acid
• 3,4-Di-O-Caffeoylquinic acid
• 45777W94HK
• CHEBI:5995
• CHEMBL249448
• UNII-45777W94HK
• 89886-31-7
• Cyclohexanecarboxylic acid, 3,4-bis(((2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-1,5-dihydroxy-, (1S,3R,4R,5R)-
• Cyclohexanecarboxylic acid, 3,4-bis((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-1,5-dihydroxy-, (1S,3R,4R,5R)-
• 3,4-dicaffeoyl quinic acid
• 102851-07-0
• IsochlorogenicacidB
• Cyclohexanecarboxylic acid, 3,4-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-1,5-dihydroxy-, (1R,3S,4S,5S)-rel-
• Cyclohexanecarboxylic acid, 3,4-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,5-dihydroxy-, (1S,3R,4R,5R)-
• Isochlorogenic-acid-B
• 3,4-dicaffeoylquinate
• Rel-3,4-Dicaffeoylquinic Acid
• 4,5-Di-O-caffeoylquinic acid?
• Quinic acid 3,4-di-O-caffeate
• SCHEMBL12246115
• ACon1_002212
• GTPL12549
• HY-N0057
• BDBM50362838
• MFCD22375481
• s9274
• AKOS026673963
• CCG-269822
• CS-3769
• NCGC00179718-01
• AS-74985
• LS-185309
• Q-100168
• Q27106970
• 3,4-Di-O-caffeoylquinic acid, >=90% (LC/MS-ELSD)
• (1S,3R,4R,5R)-3,4-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,5-dihydroxycyclohexane-1-carboxylic acid
• (1S,3R,4R,5R)-3,4-bis({[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,5-dihydroxycyclohexane-1-carboxylic acid
• (1S,3R,4R,5R)-3,4-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,5-dihydroxy-cyclohexanecarboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

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%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5983	O60218	Aldo-keto reductase family 1 member B10	240 nM; 240 nM	IC50; IC50	PMID: 22236472; via Super-PRED
CHEMBL1900	P15121	Aldose reductase	78 nM; 78 nM	IC50; IC50	via Super-PRED; PMID: 22236472
CHEMBL2487	P05067	Beta amyloid A4 protein	4700 nM; 100 nM	IC50; IC50	PMID: 22921742; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.69%	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%

Plants that contains it

• Acacia aulacocarpa
• Acacia paradoxa
• Achillea clypeolata
• Acmella ciliata
• Adonis sutchuenensis
• Andrographis paniculata
• Anemonastrum flaccidum
• Angelica pubescens
• Anodendron affine
• Aralia continentalis
• Ardisia neriifolia
• Artemisia annua
• Artemisia argyi
• Artemisia capillaris
• Artemisia carvifolia
• Artemisia dracunculus
• Artemisia gmelinii
• Artemisia montana
• Artemisia princeps
• Aspidosperma subincanum
• Aster tataricus
• Astragalus ernestii
• Athanasia crithmifolia
• Baccharis dracunculifolia
• Baccharis salicifolia subsp. salicifolia
• Berberis julianae
• Berneuxia thibetica
• Bidens pilosa
• Bongardia chrysogonum
• Bridelia ferruginea
• Bystropogon origanifolius
• Cardamine heptaphylla
• Cedrela salvadorensis
• Centella asiatica
• Cerbera odollam
• Chrysanthemum indicum
• Chrysanthemum morifolium
• Cichorium intybus
• Cichorium pumilum
• Cneorum pulverulentum
• Codonocarpus attenuatus
• Coffea arabica
• Colchicum soboliferum
• Crassocephalum crepidioides
• Crateva magna
• Cressa cretica
• Cryptocarya aschersoniana
• Cuscuta chinensis
• Cynara cardunculus
• Diospyros verrucosa
• Dipsacus inermis
• Dracocephalum ruyschiana
• Eragrostis curvula
• Erigeron breviscapus
• Erycibe obtusifolia
• Erycibe schmidtii
• Euonymus nanoides
• Eupatorium argentinum
• Filago congesta
• Fritillaria meleagris
• Galium latoramosum
• Garcinia gummi-gutta
• Garcinia madruno
• Gardenia jasminoides
• Guatteria ucayalina
• Hertia cheirifolia
• Ilex taubertiana
• Ipomoea batatas
• Ipomoea cairica
• Ipomoea pes-caprae
• Isertia pittieri
• Isophysis tasmanica
• Jacobaea subalpina
• Juniperus brevifolia
• Lactuca indica
• Licaria chrysophylla
• Lonicera confusa
• Lonicera hypoglauca
• Lonicera japonica
• Lonicera macrantha
• Lychnophora pohlii
• Lychnophora staavioides
• Matricaria discoidea
• Melaleuca cuticularis
• Metasequoia glyptostroboides
• Neonauclea sessilifolia
• Nepeta multifida
• Neurolaena lobata
• Ormosia hosiei
• Ornithoglossum viride
• Ostericum grossiserratum
• Peritassa compta
• Petasites japonicus
• Petasites radiatus
• Phagnalon rupestre
• Philenoptera laxiflora
• Plantago lundborgii
• Pleogyne australis
• Polygala amara
• Psiadia dentata
• Psorothamnus spinosus
• Pteris multifida
• Pterocaulon virgatum
• Pyrola decorata
• Quercus serrata
• Rubus allegheniensis
• Salvia abrotanoides
• Saussurea involucrata
• Schizanthus tricolor
• Scorzonera latifolia
• Scorzonera veratrifolia
• Sideritis arborescens
• Siphonostegia chinensis
• Solanum pseudoquina
• Solidago altissima
• Solidago canadensis
• Sphaeranthus confertifolius
• Stenostomum acreanum
• Stephania sutchuenensis
• Strychnos axillaris
• Strychnos lucida
• Swertia japonica
• Taraxacum coreanum
• Taraxacum mongolicum
• Taraxacum officinale
• Taraxacum platycarpum
• Taraxacum sinicum
• Tetraneuris acaulis
• Trachelospermum asiaticum
• Triadica sebifera
• Tripolium pannonicum
• Tussilago farfara
• Unonopsis glaucopetala
• Vachellia pennatula
• Vepris gabonensis
• Vitex negundo
• Xanthium strumarium subsp. strumarium
• Youngia japonica
• Zieria smithii

Cross-Links

• PubChem: 5281780
• NPASS: NPC224389
• ChEMBL: CHEMBL249448
• LOTUS: LTS0046605
• wikiData: Q27106970