Kaempferol 3-O-Alpha-L-Arabinopyranosyl-7-O-Alpha-L-Rhamnopyranoside

Details

• Internal ID: 020576e2-6dde-4091-bbc9-e5b88c92fb3c
• 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)-3,4,5-trihydroxyoxan-2-yl]oxychromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2=CC(=C3C(=C2)OC(=C(C3=O)OC4C(C(C(CO4)O)O)O)C5=CC=C(C=C5)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](CO4)O)O)O)C5=CC=C(C=C5)O)O)O)O)O
• InChI: InChI=1S/C26H28O14/c1-9-17(30)20(33)22(35)26(37-9)38-12-6-13(28)16-15(7-12)39-23(10-2-4-11(27)5-3-10)24(19(16)32)40-25-21(34)18(31)14(29)8-36-25/h2-7,9,14,17-18,20-22,25-31,33-35H,8H2,1H3/t9-,14-,17-,18-,20+,21+,22+,25-,26-/m0/s1
• InChI Key: DQBVFTJNUYZVQL-CLFUFSEMSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₂₈O₁₄
• Molecular Weight: 564.50 g/mol
• Exact Mass: 564.14790556 g/mol
• Topological Polar Surface Area (TPSA): 225.00 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): -1.10
• H-Bond Acceptor: 14
• H-Bond Donor: 8
• Rotatable Bonds: 5

Synonyms

• CHEBI:68878
• kaempferol 3-O-alpha-L-arabinopyranosyl-7-O-alpha-L-rhamnopyranoside
• 71801-96-2
• Compound NP-023300
• BDBM50359310
• AKOS040734469
• Q27137234
• 3-(alpha-L-Arabinopyranosyloxy)-4',5-dihydroxy-7-(alpha-L-rhamnopyranosyloxy)flavone
• 3-(alpha-L-arabinopyranosyloxy)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl 6-deoxy-alpha-L-mannopyranoside
• 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)-3,4,5-trihydroxyoxan-2-yl]oxychromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7160	71.60%
Caco-2	-	0.9098	90.98%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.6720	67.20%
OATP2B1 inhibitior	-	0.5537	55.37%
OATP1B1 inhibitior	+	0.9227	92.27%
OATP1B3 inhibitior	+	0.8917	89.17%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8343	83.43%
P-glycoprotein inhibitior	-	0.5355	53.55%
P-glycoprotein substrate	+	0.5114	51.14%
CYP3A4 substrate	+	0.6533	65.33%
CYP2C9 substrate	-	0.7354	73.54%
CYP2D6 substrate	-	0.8607	86.07%
CYP3A4 inhibition	-	0.9278	92.78%
CYP2C9 inhibition	-	0.9538	95.38%
CYP2C19 inhibition	-	0.9355	93.55%
CYP2D6 inhibition	-	0.9268	92.68%
CYP1A2 inhibition	-	0.8650	86.50%
CYP2C8 inhibition	+	0.7543	75.43%
CYP inhibitory promiscuity	-	0.8976	89.76%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6476	64.76%
Eye corrosion	-	0.9928	99.28%
Eye irritation	-	0.8884	88.84%
Skin irritation	-	0.7836	78.36%
Skin corrosion	-	0.9497	94.97%
Ames mutagenesis	+	0.6263	62.63%
Human Ether-a-go-go-Related Gene inhibition	+	0.7243	72.43%
Micronuclear	+	0.7433	74.33%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.9187	91.87%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.9343	93.43%
Acute Oral Toxicity (c)	III	0.5953	59.53%
Estrogen receptor binding	+	0.7475	74.75%
Androgen receptor binding	+	0.6611	66.11%
Thyroid receptor binding	-	0.5239	52.39%
Glucocorticoid receptor binding	+	0.6387	63.87%
Aromatase binding	-	0.4928	49.28%
PPAR gamma	+	0.6887	68.87%
Honey bee toxicity	-	0.7437	74.37%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5450	54.50%
Fish aquatic toxicity	+	0.8557	85.57%

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	99.36%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	99.29%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.60%	89.00%
CHEMBL2581	P07339	Cathepsin D	96.77%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.77%	94.00%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	93.92%	95.64%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.10%	86.33%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	90.81%	90.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.69%	99.15%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.76%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	89.60%	94.73%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.30%	85.14%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	88.90%	95.78%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.73%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.97%	96.09%
CHEMBL4208	P20618	Proteasome component C5	87.05%	90.00%
CHEMBL242	Q92731	Estrogen receptor beta	84.77%	98.35%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.93%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.76%	99.23%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.33%	97.36%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	80.65%	95.53%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.12%	95.89%

Plants that contains it

• Indigofera hebepetala
• Lotus hirsutus
• Vicia faba

Cross-Links

• PubChem: 57401109
• NPASS: NPC276377
• LOTUS: LTS0198746
• wikiData: Q27137234