methyl 3,5-di-O-caffeoyl quinate

Details

• Internal ID: 0bb8811c-1df4-4820-b42e-892d3721c7de
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Alcohols and polyols > Cyclitols and derivatives > Quinic acids and derivatives
• IUPAC Name: methyl (3R,5R)-3,5-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,4-dihydroxycyclohexane-1-carboxylate
• SMILES (Canonical): COC(=O)C1(CC(C(C(C1)OC(=O)C=CC2=CC(=C(C=C2)O)O)O)OC(=O)C=CC3=CC(=C(C=C3)O)O)O
• SMILES (Isomeric): COC(=O)C1(C[C@H](C([C@@H](C1)OC(=O)/C=C/C2=CC(=C(C=C2)O)O)O)OC(=O)/C=C/C3=CC(=C(C=C3)O)O)O
• InChI: InChI=1S/C26H26O12/c1-36-25(34)26(35)12-20(37-22(31)8-4-14-2-6-16(27)18(29)10-14)24(33)21(13-26)38-23(32)9-5-15-3-7-17(28)19(30)11-15/h2-11,20-21,24,27-30,33,35H,12-13H2,1H3/b8-4+,9-5+/t20-,21-,24?,26?/m1/s1
• InChI Key: VEBNYMXKXIIGFX-IYVYCCGLSA-N
• Popularity: 50 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₂₆O₁₂
• Molecular Weight: 530.50 g/mol
• Exact Mass: 530.14242626 g/mol
• Topological Polar Surface Area (TPSA): 200.00 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 1.12
• H-Bond Acceptor: 12
• H-Bond Donor: 6
• Rotatable Bonds: 7

Synonyms

• 159934-13-1
• CHEBI:66708
• methyl 3,5-di-O-caffeoyl quinate
• 3,5-Dicaffeoylquinic Acid Methyl Ester
• CHEMBL463337
• methyl (3R,5R)-3,5-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,4-dihydroxycyclohexane-1-carboxylate
• methyl (3R,5R)-3,5-bis{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4-dihydroxycyclohexanecarboxylate
• Me-3,5-diCQA
• Methyl 3,5-dicaffeoylquinate
• CHEMBL4125897
• VEBNYMXKXIIGFX-IYVYCCGLSA-N
• BDBM50163307
• AKOS040761072
• Q27135330
• 1alpha,4alpha-Dihydroxy-3beta,5alpha-bis[3-(3,4-dihydroxyphenyl)propenoyloxy]cyclohexanecarboxylic acid methyl ester
• methyl (3R,5R)-3,5-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,4-dihydroxy-cyclohexanecarboxylate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9692	96.92%
Caco-2	-	0.8844	88.44%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.8048	80.48%
OATP2B1 inhibitior	-	0.7126	71.26%
OATP1B1 inhibitior	+	0.9635	96.35%
OATP1B3 inhibitior	+	0.9417	94.17%
MATE1 inhibitior	-	0.6200	62.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.8569	85.69%
P-glycoprotein inhibitior	+	0.7164	71.64%
P-glycoprotein substrate	-	0.7804	78.04%
CYP3A4 substrate	+	0.5736	57.36%
CYP2C9 substrate	-	0.7984	79.84%
CYP2D6 substrate	-	0.8434	84.34%
CYP3A4 inhibition	-	0.9140	91.40%
CYP2C9 inhibition	-	0.8834	88.34%
CYP2C19 inhibition	-	0.8842	88.42%
CYP2D6 inhibition	-	0.9560	95.60%
CYP1A2 inhibition	-	0.7419	74.19%
CYP2C8 inhibition	-	0.5719	57.19%
CYP inhibitory promiscuity	-	0.9797	97.97%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8743	87.43%
Carcinogenicity (trinary)	Non-required	0.5850	58.50%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9142	91.42%
Skin irritation	-	0.7319	73.19%
Skin corrosion	-	0.9056	90.56%
Ames mutagenesis	-	0.7800	78.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7050	70.50%
Micronuclear	+	0.6000	60.00%
Hepatotoxicity	+	0.6500	65.00%
skin sensitisation	-	0.7560	75.60%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.8708	87.08%
Acute Oral Toxicity (c)	III	0.6610	66.10%
Estrogen receptor binding	+	0.8006	80.06%
Androgen receptor binding	+	0.7669	76.69%
Thyroid receptor binding	+	0.6054	60.54%
Glucocorticoid receptor binding	+	0.7389	73.89%
Aromatase binding	-	0.5594	55.94%
PPAR gamma	+	0.6339	63.39%
Honey bee toxicity	-	0.8365	83.65%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9891	98.91%

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	99.80%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.67%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.18%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.66%	95.56%
CHEMBL4208	P20618	Proteasome component C5	90.63%	90.00%
CHEMBL1951	P21397	Monoamine oxidase A	90.49%	91.49%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.02%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	89.05%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.40%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.75%	89.00%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	87.11%	91.03%
CHEMBL4040	P28482	MAP kinase ERK2	85.72%	83.82%
CHEMBL3194	P02766	Transthyretin	83.80%	90.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.55%	97.09%
CHEMBL2179	P04062	Beta-glucocerebrosidase	82.18%	85.31%
CHEMBL2535	P11166	Glucose transporter	81.94%	98.75%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.67%	91.07%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.53%	95.89%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.13%	85.14%
CHEMBL2581	P07339	Cathepsin D	81.07%	98.95%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.36%	95.50%

Plants that contains it

• Akebia quinata
• Akebia trifoliata
• Artemisia ludoviciana
• Lonicera confusa
• Lonicera hypoglauca
• Lonicera macrantha

Cross-Links

• PubChem: 10075681
• NPASS: NPC237314
• LOTUS: LTS0262950
• wikiData: Q103813556