Kaempferol 3-gentiobioside-7-rhamnoside

Details

• Internal ID: 08c3278b-f2f6-4dca-b649-b49fda88cef2
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2=CC(=C3C(=C2)OC(=C(C3=O)OC4C(C(C(C(O4)COC5C(C(C(C(O5)CO)O)O)O)O)O)O)C6=CC=C(C=C6)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=CC(=C3C(=C2)OC(=C(C3=O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)O)O)C6=CC=C(C=C6)O)O)O)O)O
• InChI: InChI=1S/C33H40O20/c1-10-19(37)23(41)27(45)32(48-10)49-13-6-14(36)18-15(7-13)50-29(11-2-4-12(35)5-3-11)30(22(18)40)53-33-28(46)25(43)21(39)17(52-33)9-47-31-26(44)24(42)20(38)16(8-34)51-31/h2-7,10,16-17,19-21,23-28,31-39,41-46H,8-9H2,1H3/t10-,16+,17+,19-,20+,21+,23+,24-,25-,26+,27+,28+,31+,32-,33-/m0/s1
• InChI Key: QFSDWLPMRWDFID-CSNYLUTCSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₄₀O₂₀
• Molecular Weight: 756.70 g/mol
• Exact Mass: 756.21129366 g/mol
• Topological Polar Surface Area (TPSA): 324.00 Ų
• XlogP: -2.70
• Atomic LogP (AlogP): -3.92
• H-Bond Acceptor: 20
• H-Bond Donor: 12
• Rotatable Bonds: 9

Synonyms

• 173740-43-7
• Kaempferol 3-glucoside-(1->6)-glucoside-7-alpha-L-rhamnoside
• CHEBI:133218
• DTXSID701175980
• Kaempferol 3-coumaroyl-triglucoside
• kaempferol 3-O-gentiobioside-7-O-rhamnoside
• Kampferol 3-(6-glucosylglucoside) 7-rhamnoside
• kaempferol 3-O-glucosyl(1->6)glucoside-7-O-rhamnoside
• kaempferol-3-O-beta-gentiobioside-7-O-alpha-L-rhamnoside
• kaempferol-3-O-[glucopyranosyl(1-6)glucopyranoside]-7-O-rhamnopyranoside
• 3-O-beta-D-Glucosyl-(1-->6)-beta-D-glucosyl-7-O-alpha-L-rhamnosylkaempferol
• 5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
• 7-[(6-deoxy-alpha-L-mannopyranosyl)oxy]-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-3-yl 6-O-beta-D-glucopyranosyl-beta-D-glucopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5372	53.72%
Caco-2	-	0.9097	90.97%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.6684	66.84%
OATP2B1 inhibitior	-	0.7121	71.21%
OATP1B1 inhibitior	+	0.9024	90.24%
OATP1B3 inhibitior	+	0.9642	96.42%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.8257	82.57%
P-glycoprotein inhibitior	-	0.4633	46.33%
P-glycoprotein substrate	+	0.5296	52.96%
CYP3A4 substrate	+	0.6315	63.15%
CYP2C9 substrate	-	0.6986	69.86%
CYP2D6 substrate	-	0.8617	86.17%
CYP3A4 inhibition	-	0.9550	95.50%
CYP2C9 inhibition	-	0.9252	92.52%
CYP2C19 inhibition	-	0.9129	91.29%
CYP2D6 inhibition	-	0.9613	96.13%
CYP1A2 inhibition	-	0.8948	89.48%
CYP2C8 inhibition	+	0.7768	77.68%
CYP inhibitory promiscuity	-	0.6991	69.91%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6759	67.59%
Eye corrosion	-	0.9929	99.29%
Eye irritation	-	0.9056	90.56%
Skin irritation	-	0.8374	83.74%
Skin corrosion	-	0.9635	96.35%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8234	82.34%
Micronuclear	+	0.6333	63.33%
Hepatotoxicity	-	0.6750	67.50%
skin sensitisation	-	0.9289	92.89%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.8246	82.46%
Acute Oral Toxicity (c)	III	0.5567	55.67%
Estrogen receptor binding	+	0.8001	80.01%
Androgen receptor binding	+	0.5740	57.40%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.5184	51.84%
Aromatase binding	+	0.5450	54.50%
PPAR gamma	+	0.7280	72.80%
Honey bee toxicity	-	0.7572	75.72%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5650	56.50%
Fish aquatic toxicity	+	0.8024	80.24%

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	99.40%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.74%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	97.50%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.01%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.16%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.39%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	93.69%	94.73%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.23%	99.15%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	90.70%	95.64%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.43%	96.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	90.38%	86.92%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.21%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.84%	99.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.31%	85.14%
CHEMBL242	Q92731	Estrogen receptor beta	86.22%	98.35%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	85.93%	95.78%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.86%	95.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.98%	95.89%
CHEMBL3714130	P46095	G-protein coupled receptor 6	83.30%	97.36%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.89%	94.80%
CHEMBL3194	P02766	Transthyretin	80.55%	90.71%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.03%	95.83%

Plants that contains it

• Arabidopsis thaliana
• Breynia androgyna

Cross-Links

• PubChem: 10652679
• NPASS: NPC178743
• LOTUS: LTS0180914
• wikiData: Q23417271