ethyl 5-O-caffeoyl-4-O-sinapoylquinate

Details

• Internal ID: e123ca9f-60b5-45fb-8ada-436f480ae9d8
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Alcohols and polyols > Cyclitols and derivatives > Quinic acids and derivatives
• IUPAC Name: ethyl (1S,3R,4R,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,5-dihydroxy-4-[(E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxycyclohexane-1-carboxylate
• SMILES (Canonical): CCOC(=O)C1(CC(C(C(C1)OC(=O)C=CC2=CC(=C(C=C2)O)O)OC(=O)C=CC3=CC(=C(C(=C3)OC)O)OC)O)O
• SMILES (Isomeric): CCOC(=O)[C@@]1(C[C@H]([C@H]([C@@H](C1)OC(=O)/C=C/C2=CC(=C(C=C2)O)O)OC(=O)/C=C/C3=CC(=C(C(=C3)OC)O)OC)O)O
• InChI: InChI=1S/C29H32O13/c1-4-40-28(36)29(37)14-20(32)27(23(15-29)41-24(33)9-6-16-5-8-18(30)19(31)11-16)42-25(34)10-7-17-12-21(38-2)26(35)22(13-17)39-3/h5-13,20,23,27,30-32,35,37H,4,14-15H2,1-3H3/b9-6+,10-7+/t20-,23-,27-,29+/m1/s1
• InChI Key: WTUPZYOQFGPHOS-QIOUUQIKSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₂O₁₃
• Molecular Weight: 588.60 g/mol
• Exact Mass: 588.18429107 g/mol
• Topological Polar Surface Area (TPSA): 199.00 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 1.82
• H-Bond Acceptor: 13
• H-Bond Donor: 5
• Rotatable Bonds: 10

Synonyms

• BDBM50478841
• ethyl 5-O-caffeoyl-4-O-sinapoylquinate
• ethyl (1S,3R,4R,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,5-dihydroxy-4-[(E)-3-(4-hydroxy-3,5-dimethoxy-phenyl)prop-2-enoyl]oxy-cyclohexanecarboxylate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8972	89.72%
Caco-2	-	0.8772	87.72%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.8235	82.35%
OATP2B1 inhibitior	-	0.7190	71.90%
OATP1B1 inhibitior	+	0.9145	91.45%
OATP1B3 inhibitior	+	0.9228	92.28%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.9574	95.74%
P-glycoprotein inhibitior	+	0.7815	78.15%
P-glycoprotein substrate	-	0.5697	56.97%
CYP3A4 substrate	+	0.6539	65.39%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8428	84.28%
CYP3A4 inhibition	-	0.6572	65.72%
CYP2C9 inhibition	-	0.7157	71.57%
CYP2C19 inhibition	-	0.7633	76.33%
CYP2D6 inhibition	-	0.8825	88.25%
CYP1A2 inhibition	-	0.5331	53.31%
CYP2C8 inhibition	+	0.5919	59.19%
CYP inhibitory promiscuity	-	0.8680	86.80%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8721	87.21%
Carcinogenicity (trinary)	Non-required	0.7257	72.57%
Eye corrosion	-	0.9935	99.35%
Eye irritation	-	0.9246	92.46%
Skin irritation	-	0.8252	82.52%
Skin corrosion	-	0.9432	94.32%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7321	73.21%
Micronuclear	-	0.5034	50.34%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.7785	77.85%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.9642	96.42%
Acute Oral Toxicity (c)	III	0.7020	70.20%
Estrogen receptor binding	+	0.7970	79.70%
Androgen receptor binding	+	0.7538	75.38%
Thyroid receptor binding	+	0.6195	61.95%
Glucocorticoid receptor binding	+	0.7586	75.86%
Aromatase binding	-	0.4862	48.62%
PPAR gamma	+	0.6327	63.27%
Honey bee toxicity	-	0.7903	79.03%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5055	50.55%
Fish aquatic toxicity	+	0.9900	99.00%

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	99.44%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.59%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	97.22%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.63%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.05%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.70%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.12%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.65%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	92.24%	90.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.96%	97.09%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	89.47%	89.62%
CHEMBL2179	P04062	Beta-glucocerebrosidase	88.97%	85.31%
CHEMBL4208	P20618	Proteasome component C5	88.61%	90.00%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	86.67%	97.21%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	85.55%	92.68%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.16%	92.94%
CHEMBL3194	P02766	Transthyretin	83.17%	90.71%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.95%	95.89%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.72%	96.95%
CHEMBL3492	P49721	Proteasome Macropain subunit	82.52%	90.24%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.26%	92.62%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.76%	100.00%
CHEMBL2581	P07339	Cathepsin D	81.25%	98.95%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.18%	95.50%

Plants that contains it

• Gardenia jasminoides

Cross-Links

• PubChem: 11512664
• NPASS: NPC19380
• LOTUS: LTS0088161
• wikiData: Q105312803