Kaempferol-3-O-(2,3,4-Tri-O-Acetyl-Alpha-L-Rhamnopyranoside)

Details

• Internal ID: 7b8abc32-1d6a-47ad-9a4f-b08548f75de6
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: [(2S,3S,4R,5R,6S)-4,5-diacetyloxy-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy-2-methyloxan-3-yl] acetate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC=C(C=C4)O)OC(=O)C)OC(=O)C)OC(=O)C
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC=C(C=C4)O)OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C27H26O13/c1-11-22(36-12(2)28)25(37-13(3)29)26(38-14(4)30)27(35-11)40-24-21(34)20-18(33)9-17(32)10-19(20)39-23(24)15-5-7-16(31)8-6-15/h5-11,22,25-27,31-33H,1-4H3/t11-,22-,25+,26+,27-/m0/s1
• InChI Key: OFWDHNGVKNRLFY-LHZKXVGGSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₂₆O₁₃
• Molecular Weight: 558.50 g/mol
• Exact Mass: 558.13734088 g/mol
• Topological Polar Surface Area (TPSA): 184.00 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 2.50
• H-Bond Acceptor: 13
• H-Bond Donor: 3
• Rotatable Bonds: 6

Synonyms

• CHEMBL519761
• SCHEMBL571210
• OFWDHNGVKNRLFY-LHZKXVGGSA-N
• BDBM50242097
• kaempferol-3-O-(2,3,4-tri-O-acetyl-alpha-L-rhamnopyranoside)
• 3-(2-O,3-O,4-O-Triacetyl-alpha-L-rhamnopyranosyloxy)-4',5,7-trihydroxyflavone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8335	83.35%
Caco-2	-	0.7888	78.88%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.7061	70.61%
OATP2B1 inhibitior	-	0.5733	57.33%
OATP1B1 inhibitior	+	0.8413	84.13%
OATP1B3 inhibitior	-	0.3604	36.04%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.9085	90.85%
P-glycoprotein inhibitior	+	0.8547	85.47%
P-glycoprotein substrate	-	0.5817	58.17%
CYP3A4 substrate	+	0.6522	65.22%
CYP2C9 substrate	+	0.5839	58.39%
CYP2D6 substrate	-	0.8870	88.70%
CYP3A4 inhibition	-	0.8575	85.75%
CYP2C9 inhibition	-	0.8462	84.62%
CYP2C19 inhibition	-	0.9348	93.48%
CYP2D6 inhibition	-	0.9559	95.59%
CYP1A2 inhibition	-	0.8264	82.64%
CYP2C8 inhibition	+	0.8444	84.44%
CYP inhibitory promiscuity	-	0.6478	64.78%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5276	52.76%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.8646	86.46%
Skin irritation	-	0.7512	75.12%
Skin corrosion	-	0.9552	95.52%
Ames mutagenesis	+	0.5363	53.63%
Human Ether-a-go-go-Related Gene inhibition	-	0.4516	45.16%
Micronuclear	+	0.8800	88.00%
Hepatotoxicity	-	0.5072	50.72%
skin sensitisation	-	0.9336	93.36%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.6826	68.26%
Acute Oral Toxicity (c)	III	0.5465	54.65%
Estrogen receptor binding	+	0.8011	80.11%
Androgen receptor binding	+	0.8368	83.68%
Thyroid receptor binding	+	0.5526	55.26%
Glucocorticoid receptor binding	+	0.7555	75.55%
Aromatase binding	-	0.6593	65.93%
PPAR gamma	+	0.7275	72.75%
Honey bee toxicity	-	0.8010	80.10%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5450	54.50%
Fish aquatic toxicity	+	0.9663	96.63%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL289	P10635	Cytochrome P450 2D6	43300 nM	IC50	PMID: 22530813
CHEMBL340	P08684	Cytochrome P450 3A4	14400 nM	IC50	PMID: 18077363

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.82%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.79%	89.00%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	97.13%	95.64%
CHEMBL2581	P07339	Cathepsin D	97.09%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.74%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.70%	94.00%
CHEMBL1951	P21397	Monoamine oxidase A	93.47%	91.49%
CHEMBL3401	O75469	Pregnane X receptor	90.87%	94.73%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.92%	99.15%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.07%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.26%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.97%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.46%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.85%	99.23%
CHEMBL3194	P02766	Transthyretin	85.83%	90.71%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	85.05%	95.78%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.41%	85.14%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	83.60%	94.42%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.95%	95.89%
CHEMBL4208	P20618	Proteasome component C5	82.53%	90.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	82.38%	94.80%
CHEMBL340	P08684	Cytochrome P450 3A4	81.46%	91.19%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	81.43%	93.65%

Plants that contains it

• Zingiber zerumbet

Cross-Links

• PubChem: 11364979
• NPASS: NPC104677
• ChEMBL: CHEMBL519761