3-O-Kaempferol 2,6-di-O-(cis/trans-p-coumaroyl)-beta-D-glucopyranoside

Details

• Internal ID: a9429084-f3da-400b-83e7-f422303657cb
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid 3-O-p-coumaroyl glycosides
• IUPAC Name: [(2R,3S,4S,5R,6S)-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy-3,4-dihydroxy-5-[(Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxyoxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
• SMILES (Canonical): C1=CC(=CC=C1C=CC(=O)OCC2C(C(C(C(O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC=C(C=C5)O)OC(=O)C=CC6=CC=C(C=C6)O)O)O)O
• SMILES (Isomeric): C1=CC(=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)OC(=O)/C=C\C6=CC=C(C=C6)O)O)O)O
• InChI: InChI=1S/C39H32O15/c40-23-9-1-20(2-10-23)5-15-30(45)50-19-29-33(47)35(49)38(53-31(46)16-6-21-3-11-24(41)12-4-21)39(52-29)54-37-34(48)32-27(44)17-26(43)18-28(32)51-36(37)22-7-13-25(42)14-8-22/h1-18,29,33,35,38-44,47,49H,19H2/b15-5+,16-6-/t29-,33-,35+,38-,39+/m1/s1
• InChI Key: YXXQUJGFZPLXJV-TXPPTBEJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₉H₃₂O₁₅
• Molecular Weight: 740.70 g/mol
• Exact Mass: 740.17412031 g/mol
• Topological Polar Surface Area (TPSA): 239.00 Ų
• XlogP: 4.80
• Atomic LogP (AlogP): 3.70
• H-Bond Acceptor: 15
• H-Bond Donor: 7
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4689	46.89%
Caco-2	-	0.8959	89.59%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.5846	58.46%
OATP2B1 inhibitior	-	0.7025	70.25%
OATP1B1 inhibitior	+	0.8353	83.53%
OATP1B3 inhibitior	+	0.9635	96.35%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.7502	75.02%
P-glycoprotein inhibitior	+	0.7549	75.49%
P-glycoprotein substrate	-	0.5692	56.92%
CYP3A4 substrate	+	0.6717	67.17%
CYP2C9 substrate	-	0.8105	81.05%
CYP2D6 substrate	-	0.8724	87.24%
CYP3A4 inhibition	-	0.8901	89.01%
CYP2C9 inhibition	-	0.8448	84.48%
CYP2C19 inhibition	-	0.8659	86.59%
CYP2D6 inhibition	-	0.9392	93.92%
CYP1A2 inhibition	-	0.9312	93.12%
CYP2C8 inhibition	+	0.8947	89.47%
CYP inhibitory promiscuity	-	0.7755	77.55%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6770	67.70%
Eye corrosion	-	0.9922	99.22%
Eye irritation	-	0.8909	89.09%
Skin irritation	-	0.8069	80.69%
Skin corrosion	-	0.9555	95.55%
Ames mutagenesis	+	0.5063	50.63%
Human Ether-a-go-go-Related Gene inhibition	-	0.4621	46.21%
Micronuclear	+	0.7292	72.92%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.8777	87.77%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.9684	96.84%
Acute Oral Toxicity (c)	III	0.4048	40.48%
Estrogen receptor binding	+	0.7800	78.00%
Androgen receptor binding	+	0.8047	80.47%
Thyroid receptor binding	+	0.5344	53.44%
Glucocorticoid receptor binding	+	0.6140	61.40%
Aromatase binding	-	0.5185	51.85%
PPAR gamma	+	0.6825	68.25%
Honey bee toxicity	-	0.7366	73.66%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9677	96.77%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3729	P22748	Carbonic anhydrase IV	344.2 nM	Ki	via Super-PRED
CHEMBL2326	P43166	Carbonic anhydrase VII	4.7 nM	Ki	via Super-PRED
CHEMBL3242	O43570	Carbonic anhydrase XII	408.9 nM	Ki	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.36%	91.11%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	98.79%	95.64%
CHEMBL1806	P11388	DNA topoisomerase II alpha	98.47%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	97.70%	91.49%
CHEMBL3194	P02766	Transthyretin	96.88%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.92%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.69%	94.45%
CHEMBL2581	P07339	Cathepsin D	92.17%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.01%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	89.58%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.61%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.32%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.06%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.27%	97.09%
CHEMBL1929	P47989	Xanthine dehydrogenase	86.25%	96.12%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	85.84%	95.78%
CHEMBL4630	O14757	Serine/threonine-protein kinase Chk1	84.75%	97.03%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.00%	95.50%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.83%	99.15%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	83.82%	80.78%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.84%	86.92%
CHEMBL4208	P20618	Proteasome component C5	81.71%	90.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.63%	94.00%
CHEMBL5678	P34947	G protein-coupled receptor kinase 5	80.42%	88.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.41%	95.89%
CHEMBL242	Q92731	Estrogen receptor beta	80.02%	98.35%

Plants that contains it

• Allium neapolitanum
• Cycas armstrongii
• Cycas revoluta
• Ephedra aphylla
• Licaria armeniaca
• Mammillaria magnimamma
• Munronia pinnata
• Plectocephalus chilensis
• Quercus suber
• Trichilia hirta
• Typha domingensis

Cross-Links

• PubChem: 10439992
• NPASS: NPC25761