Quercetin 3-(6''-ferulylglucoside)

Details

• Internal ID: 228e5f69-bf0f-4d30-9fc9-09b027625af7
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid 3-O-p-coumaroyl glycosides
• IUPAC Name: [(2R,3S,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• SMILES (Canonical): COC1=C(C=CC(=C1)C=CC(=O)OCC2C(C(C(C(O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC(=C(C=C5)O)O)O)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)/C=C/C(=O)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC(=C(C=C5)O)O)O)O)O)O
• InChI: InChI=1S/C31H28O15/c1-42-20-8-13(2-5-17(20)34)3-7-23(37)43-12-22-25(38)27(40)28(41)31(45-22)46-30-26(39)24-19(36)10-15(32)11-21(24)44-29(30)14-4-6-16(33)18(35)9-14/h2-11,22,25,27-28,31-36,38,40-41H,12H2,1H3/b7-3+/t22-,25-,27+,28-,31+/m1/s1
• InChI Key: PSBFVXDMNYDZMV-SMTCTBLTSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₂₈O₁₅
• Molecular Weight: 640.50 g/mol
• Exact Mass: 640.14282018 g/mol
• Topological Polar Surface Area (TPSA): 242.00 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 1.44
• H-Bond Acceptor: 15
• H-Bond Donor: 8
• Rotatable Bonds: 8

Synonyms

• CHEBI:192447
• LMPK12112145
• quercetin 3-O-(6"-O-feruloyl)-glucoside
• [(2R,3S,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• 2-(3,4-Dihydroxyphenyl)-3-[6-O-(3-methoxy-4-hydroxycinnamoyl)-beta-D-glucopyranosyloxy]-5,7-dihydroxy-4H-1-benzopyran-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5720	57.20%
Caco-2	-	0.8935	89.35%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.5995	59.95%
OATP2B1 inhibitior	-	0.5659	56.59%
OATP1B1 inhibitior	+	0.8945	89.45%
OATP1B3 inhibitior	+	0.9809	98.09%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.6533	65.33%
P-glycoprotein inhibitior	+	0.6849	68.49%
P-glycoprotein substrate	-	0.5230	52.30%
CYP3A4 substrate	+	0.6851	68.51%
CYP2C9 substrate	-	0.8156	81.56%
CYP2D6 substrate	-	0.8653	86.53%
CYP3A4 inhibition	-	0.8925	89.25%
CYP2C9 inhibition	-	0.8007	80.07%
CYP2C19 inhibition	-	0.8490	84.90%
CYP2D6 inhibition	-	0.9305	93.05%
CYP1A2 inhibition	-	0.9125	91.25%
CYP2C8 inhibition	+	0.9268	92.68%
CYP inhibitory promiscuity	-	0.7321	73.21%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6214	62.14%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9038	90.38%
Skin irritation	-	0.8169	81.69%
Skin corrosion	-	0.9464	94.64%
Ames mutagenesis	-	0.5528	55.28%
Human Ether-a-go-go-Related Gene inhibition	+	0.6463	64.63%
Micronuclear	+	0.7292	72.92%
Hepatotoxicity	-	0.6500	65.00%
skin sensitisation	-	0.9075	90.75%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.9589	95.89%
Acute Oral Toxicity (c)	III	0.5749	57.49%
Estrogen receptor binding	+	0.7658	76.58%
Androgen receptor binding	+	0.7677	76.77%
Thyroid receptor binding	-	0.4875	48.75%
Glucocorticoid receptor binding	+	0.6901	69.01%
Aromatase binding	+	0.5377	53.77%
PPAR gamma	+	0.6644	66.44%
Honey bee toxicity	-	0.7370	73.70%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9399	93.99%

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	99.67%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	98.74%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	98.46%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	96.82%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.98%	96.09%
CHEMBL3194	P02766	Transthyretin	95.68%	90.71%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.59%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.51%	99.17%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	92.31%	95.64%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.93%	95.56%
CHEMBL2581	P07339	Cathepsin D	91.65%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.04%	85.14%
CHEMBL3401	O75469	Pregnane X receptor	88.69%	94.73%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	88.62%	80.78%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	87.72%	95.50%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.85%	94.45%
CHEMBL2002	P12268	Inosine-5'-monophosphate dehydrogenase 2	84.95%	98.21%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	84.04%	89.62%
CHEMBL4208	P20618	Proteasome component C5	83.83%	90.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.46%	94.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.17%	99.15%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.58%	90.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.45%	97.09%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	82.44%	95.78%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.45%	94.33%

Plants that contains it

• Baphia pubescens
• Lasiosiphon kraussianus
• Morinda morindoides
• Petrosedum pruinatum
• Populus angustifolia
• Sasa senanensis

Cross-Links

• PubChem: 11114901
• NPASS: NPC4586