Kaempferol-3-O-(2''-O-beta-D-glucopyl)-beta-D-rutinoside

Details

• Internal ID: 660d4517-105d-4bc3-ac57-92cf6d3197ac
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC=C(C=C5)O)OC6C(C(C(C(O6)CO)O)O)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)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[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)O)O)O)O)O
• InChI: InChI=1S/C33H40O20/c1-10-19(38)23(42)26(45)31(48-10)47-9-17-21(40)25(44)30(53-32-27(46)24(43)20(39)16(8-34)50-32)33(51-17)52-29-22(41)18-14(37)6-13(36)7-15(18)49-28(29)11-2-4-12(35)5-3-11/h2-7,10,16-17,19-21,23-27,30-40,42-46H,8-9H2,1H3/t10-,16+,17+,19-,20+,21+,23+,24-,25-,26+,27+,30+,31+,32-,33-/m0/s1
• InChI Key: VNLOLXSJMINBIS-CFRIXVKNSA-N
• Popularity: 4 references 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: -2.50
• Atomic LogP (AlogP): -3.57
• H-Bond Acceptor: 20
• H-Bond Donor: 12
• Rotatable Bonds: 9

Synonyms

• Camelliaside A
• Kaempferol-3-O-(2''-O-beta-D-glucopyl)-beta-D-rutinoside
• Kaempferol-3-O-(2"-O-beta-D-glucopyl)-beta-D-rutinoside
• Kaempferol-3-O-(2''-O-|A-D-glucopyl)-|A-D-rutinoside
• 135095-52-2
• DTXSID501100551
• HY-N5119
• AKOS040758195
• MS-31341
• PD164913
• CS-0032436
• E88673
• Kaempferol 3-O-beta-D-2-(glucosyl-rutinoside)
• Kaempferol-3-O-(2"-O-beta-D- glucopyl)-beta-D-rutinoside
• Kaempferol-3-O-(2''-O-??-D-glucopyl)-??-D-rutinoside
• Kaempferol-3-O-(2'-O-beta-D-glucopyl)-beta-D-rutinoside
• 3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
• 3-[(O-6-Deoxy-alpha-L-mannopyranosyl-(1-->6)-O-[beta-D-glucopyranosyl-(1-->2)]-beta-D-glucopyranosyl)oxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5372	53.72%
Caco-2	-	0.9198	91.98%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.6684	66.84%
OATP2B1 inhibitior	-	0.7126	71.26%
OATP1B1 inhibitior	+	0.8714	87.14%
OATP1B3 inhibitior	+	0.9642	96.42%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.7054	70.54%
P-glycoprotein inhibitior	-	0.5621	56.21%
P-glycoprotein substrate	+	0.5881	58.81%
CYP3A4 substrate	+	0.6670	66.70%
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	+	0.8151	81.51%
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	-	0.9120	91.20%
Skin irritation	-	0.8374	83.74%
Skin corrosion	-	0.9635	96.35%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7222	72.22%
Micronuclear	+	0.6333	63.33%
Hepatotoxicity	-	0.6000	60.00%
skin sensitisation	-	0.9289	92.89%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.8535	85.35%
Acute Oral Toxicity (c)	III	0.5567	55.67%
Estrogen receptor binding	+	0.8193	81.93%
Androgen receptor binding	+	0.6044	60.44%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.5060	50.60%
Aromatase binding	+	0.6052	60.52%
PPAR gamma	+	0.7364	73.64%
Honey bee toxicity	-	0.7206	72.06%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5450	54.50%
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	99.50%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.91%	89.00%
CHEMBL2581	P07339	Cathepsin D	97.68%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	97.43%	91.49%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.23%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.15%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	93.79%	94.73%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	92.92%	95.64%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.98%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.58%	96.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.12%	86.92%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.27%	95.56%
CHEMBL3194	P02766	Transthyretin	85.97%	90.71%
CHEMBL3714130	P46095	G-protein coupled receptor 6	85.04%	97.36%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.54%	99.15%
CHEMBL242	Q92731	Estrogen receptor beta	84.26%	98.35%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	82.75%	95.78%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	82.57%	93.10%
CHEMBL1937	Q92769	Histone deacetylase 2	82.44%	94.75%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.72%	95.89%

Plants that contains it

• Hosta ventricosa
• Hydrangea macrophylla
• Styphnolobium japonicum

Cross-Links

• PubChem: 21676305
• LOTUS: LTS0036459
• wikiData: Q105289709