kaempferol 3-O-[alpha-L-rhamnopyranosyl(1->2)-beta-D-glucopyranosyl]-7-O-alpha-L-rhamnopyranoside

Details

• Internal ID: 1b9f4085-da24-4738-a2ce-e3180150ce5a
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=C(OC4=CC(=CC(=C4C3=O)O)OC5C(C(C(C(O5)C)O)O)O)C6=CC=C(C=C6)O)CO)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2OC3=C(OC4=CC(=CC(=C4C3=O)O)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)O)O)O)C6=CC=C(C=C6)O)CO)O)O)O)O)O
• InChI: InChI=1S/C33H40O19/c1-10-19(37)23(41)26(44)31(46-10)48-14-7-15(36)18-16(8-14)49-28(12-3-5-13(35)6-4-12)29(22(18)40)51-33-30(25(43)21(39)17(9-34)50-33)52-32-27(45)24(42)20(38)11(2)47-32/h3-8,10-11,17,19-21,23-27,30-39,41-45H,9H2,1-2H3/t10-,11-,17+,19-,20-,21+,23+,24+,25-,26+,27+,30+,31-,32-,33-/m0/s1
• InChI Key: DDELFAUOHDSZJL-CPGGTDLHSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₄₀O₁₉
• Molecular Weight: 740.70 g/mol
• Exact Mass: 740.21637904 g/mol
• Topological Polar Surface Area (TPSA): 304.00 Ų
• XlogP: -1.70
• Atomic LogP (AlogP): -2.89
• H-Bond Acceptor: 19
• H-Bond Donor: 11
• Rotatable Bonds: 8

Synonyms

• CHEBI:68879
• kaempferol 3-O-[alpha-L-rhamnopyranosyl(1->2)-beta-D-glucopyranosyl]-7-O-alpha-L-rhamnopyranoside
• Kaempferol-3-Glucoside-2''-Rhamnoside-7-Rhamnoside
• 162062-89-7
• DTXSID101346628
• BDBM50359311
• Kaempferol 3-O-Rha(1-2)Glc 7-O-Rha
• Q27137235
• 3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
• 4',5-Dihydroxy-7alpha-(alpha-L-rhamnopyranosyloxy)-3-(2-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranosyloxy)flavone
• 7-[(6-deoxy-alpha-L-mannopyranosyl)oxy]-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl 2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5000	50.00%
Caco-2	-	0.9114	91.14%
Blood Brain Barrier	-	0.8750	87.50%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.6981	69.81%
OATP2B1 inhibitior	-	0.7135	71.35%
OATP1B1 inhibitior	+	0.9204	92.04%
OATP1B3 inhibitior	+	0.9477	94.77%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.9010	90.10%
P-glycoprotein inhibitior	-	0.4641	46.41%
P-glycoprotein substrate	-	0.5183	51.83%
CYP3A4 substrate	+	0.6547	65.47%
CYP2C9 substrate	-	0.6986	69.86%
CYP2D6 substrate	-	0.8617	86.17%
CYP3A4 inhibition	-	0.9100	91.00%
CYP2C9 inhibition	-	0.9357	93.57%
CYP2C19 inhibition	-	0.9406	94.06%
CYP2D6 inhibition	-	0.9617	96.17%
CYP1A2 inhibition	-	0.8781	87.81%
CYP2C8 inhibition	+	0.7599	75.99%
CYP inhibitory promiscuity	-	0.7096	70.96%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7308	73.08%
Eye corrosion	-	0.9925	99.25%
Eye irritation	-	0.9054	90.54%
Skin irritation	-	0.8344	83.44%
Skin corrosion	-	0.9632	96.32%
Ames mutagenesis	-	0.5037	50.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.7253	72.53%
Micronuclear	+	0.6533	65.33%
Hepatotoxicity	-	0.7375	73.75%
skin sensitisation	-	0.9362	93.62%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.8773	87.73%
Acute Oral Toxicity (c)	III	0.6105	61.05%
Estrogen receptor binding	+	0.7828	78.28%
Androgen receptor binding	+	0.6394	63.94%
Thyroid receptor binding	-	0.4914	49.14%
Glucocorticoid receptor binding	-	0.4689	46.89%
Aromatase binding	+	0.5375	53.75%
PPAR gamma	+	0.7432	74.32%
Honey bee toxicity	-	0.7101	71.01%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5250	52.50%
Fish aquatic toxicity	+	0.8583	85.83%

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	99.35%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.83%	91.49%
CHEMBL2581	P07339	Cathepsin D	97.56%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.20%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.34%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.78%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	93.05%	94.73%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	91.00%	95.64%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.52%	99.15%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.34%	99.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	88.19%	86.92%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.94%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.82%	85.14%
CHEMBL3714130	P46095	G-protein coupled receptor 6	87.57%	97.36%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.86%	95.56%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	85.75%	95.78%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.76%	97.09%
CHEMBL242	Q92731	Estrogen receptor beta	84.35%	98.35%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	82.96%	93.10%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.01%	95.89%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	81.76%	96.21%
CHEMBL4208	P20618	Proteasome component C5	80.35%	90.00%

Plants that contains it

• Arabidopsis thaliana
• Camellia sinensis
• Lobularia maritima
• Lotus edulis
• Vicia faba

Cross-Links

• PubChem: 10485148
• NPASS: NPC256188
• LOTUS: LTS0069552
• wikiData: Q27137235