kaempferol 3-O-(6"-O-feruloyl)-glucoside

Details

• Internal ID: cc63a5c5-4f84-4ab0-895f-64621c87b2cf
• 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-3,4,5-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
• 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
• InChI: InChI=1S/C31H28O14/c1-41-20-10-14(2-8-18(20)34)3-9-23(36)42-13-22-25(37)27(39)28(40)31(44-22)45-30-26(38)24-19(35)11-17(33)12-21(24)43-29(30)15-4-6-16(32)7-5-15/h2-12,22,25,27-28,31-35,37,39-40H,13H2,1H3/b9-3+/t22-,25-,27+,28-,31+/m1/s1
• InChI Key: RKHQLCNACMCZQU-GWPISODLSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₂₈O₁₄
• Molecular Weight: 624.50 g/mol
• Exact Mass: 624.14790556 g/mol
• Topological Polar Surface Area (TPSA): 222.00 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 1.73
• H-Bond Acceptor: 14
• H-Bond Donor: 7
• Rotatable Bonds: 8

Synonyms

• 2-(4-Hydroxyphenyl)-3-[6-O-[(E)-3-(4-hydroxy-3-methoxyphenyl)propenoyl]-beta-D-glucopyranosyloxy]-5,7-dihydroxy-4H-1-benzopyran-4-one
• 3-[[6-O-[3-(4-Hydroxy-3-methoxyphenyl)propenoyl]-beta-D-glucopyranosyl]oxy]-4',5,7-trihydroxyflavone

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	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.5995	59.95%
OATP2B1 inhibitior	-	0.7033	70.33%
OATP1B1 inhibitior	+	0.8714	87.14%
OATP1B3 inhibitior	+	0.9809	98.09%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.7306	73.06%
P-glycoprotein inhibitior	+	0.6857	68.57%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.6806	68.06%
CYP2C9 substrate	-	0.8149	81.49%
CYP2D6 substrate	-	0.8666	86.66%
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	+	0.9181	91.81%
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	-	0.9071	90.71%
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	-	0.4020	40.20%
Micronuclear	+	0.7292	72.92%
Hepatotoxicity	-	0.7625	76.25%
skin sensitisation	-	0.9075	90.75%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.9344	93.44%
Acute Oral Toxicity (c)	III	0.5749	57.49%
Estrogen receptor binding	+	0.7480	74.80%
Androgen receptor binding	+	0.7940	79.40%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.6924	69.24%
Aromatase binding	+	0.5308	53.08%
PPAR gamma	+	0.6557	65.57%
Honey bee toxicity	-	0.7534	75.34%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
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	99.57%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	98.68%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	98.25%	86.33%
CHEMBL3194	P02766	Transthyretin	96.14%	90.71%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	96.11%	95.64%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.35%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.40%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.09%	99.17%
CHEMBL1951	P21397	Monoamine oxidase A	93.27%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.93%	95.56%
CHEMBL2581	P07339	Cathepsin D	91.42%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	88.69%	94.73%
CHEMBL4630	O14757	Serine/threonine-protein kinase Chk1	88.08%	97.03%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	87.72%	95.50%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.64%	85.14%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	87.39%	89.62%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.16%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.79%	94.00%
CHEMBL2002	P12268	Inosine-5'-monophosphate dehydrogenase 2	85.66%	98.21%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	84.28%	95.78%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.80%	99.15%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.39%	90.71%
CHEMBL4208	P20618	Proteasome component C5	82.37%	90.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.17%	97.09%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.83%	95.89%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.45%	94.33%

Plants that contains it

• Artemisia lactiflora
• Attalea phalerata
• Catalpa ovata
• Citrus medica
• Crepidiastrum sonchifolium
• Dipsacus inermis
• Duguetia calycina
• Garcinia pyrifera
• Greenwayodendron oliveri
• Jacaranda mimosifolia
• Ophryosporus floribundus
• Payena lucida
• Phalaris canariensis
• Philotheca spicata
• Plumbagella micrantha
• Polylepis incana
• Pteridium aquilinum
• Quassia indica
• Rivina humilis

Cross-Links

• PubChem: 23265189
• NPASS: NPC124752
• LOTUS: LTS0048419
• wikiData: Q76512324