kaempferol 3-O-rhamnoside-7-O-glucoside

Details

• Internal ID: 8c48901e-7323-49f0-82dd-452b08b7a62f
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2=C(OC3=CC(=CC(=C3C2=O)O)OC4C(C(C(C(O4)CO)O)O)O)C5=CC=C(C=C5)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=C(OC3=CC(=CC(=C3C2=O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)C5=CC=C(C=C5)O)O)O)O
• InChI: InChI=1S/C27H30O15/c1-9-17(31)20(34)22(36)26(38-9)42-25-19(33)16-13(30)6-12(39-27-23(37)21(35)18(32)15(8-28)41-27)7-14(16)40-24(25)10-2-4-11(29)5-3-10/h2-7,9,15,17-18,20-23,26-32,34-37H,8H2,1H3/t9-,15+,17-,18+,20+,21-,22+,23+,26-,27+/m0/s1
• InChI Key: MBLYALXOUBKFNE-SOABXMLTSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀O₁₅
• Molecular Weight: 594.50 g/mol
• Exact Mass: 594.15847025 g/mol
• Topological Polar Surface Area (TPSA): 245.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -1.74
• H-Bond Acceptor: 15
• H-Bond Donor: 9
• Rotatable Bonds: 6

Synonyms

• kaempferol 3-O-rhamnoside-7-O-glucoside
• C21854
• kaempferol 7-O-beta-D-glucoside-3-O-alpha-L-rhamnoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4777	47.77%
Caco-2	-	0.9218	92.18%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.6881	68.81%
OATP2B1 inhibitior	-	0.5547	55.47%
OATP1B1 inhibitior	+	0.9152	91.52%
OATP1B3 inhibitior	+	0.9552	95.52%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.6777	67.77%
P-glycoprotein inhibitior	-	0.5800	58.00%
P-glycoprotein substrate	-	0.6139	61.39%
CYP3A4 substrate	+	0.6194	61.94%
CYP2C9 substrate	-	0.6986	69.86%
CYP2D6 substrate	-	0.8617	86.17%
CYP3A4 inhibition	-	0.9358	93.58%
CYP2C9 inhibition	-	0.9271	92.71%
CYP2C19 inhibition	-	0.9330	93.30%
CYP2D6 inhibition	-	0.9643	96.43%
CYP1A2 inhibition	-	0.8830	88.30%
CYP2C8 inhibition	+	0.7620	76.20%
CYP inhibitory promiscuity	-	0.7188	71.88%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7023	70.23%
Eye corrosion	-	0.9927	99.27%
Eye irritation	-	0.8923	89.23%
Skin irritation	-	0.8192	81.92%
Skin corrosion	-	0.9626	96.26%
Ames mutagenesis	+	0.5063	50.63%
Human Ether-a-go-go-Related Gene inhibition	+	0.6867	68.67%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.9312	93.12%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.8518	85.18%
Acute Oral Toxicity (c)	III	0.5734	57.34%
Estrogen receptor binding	+	0.7337	73.37%
Androgen receptor binding	+	0.6128	61.28%
Thyroid receptor binding	+	0.5354	53.54%
Glucocorticoid receptor binding	-	0.4640	46.40%
Aromatase binding	-	0.4945	49.45%
PPAR gamma	+	0.7103	71.03%
Honey bee toxicity	-	0.7702	77.02%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5650	56.50%
Fish aquatic toxicity	+	0.8289	82.89%

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	99.25%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.78%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	97.44%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.82%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.92%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.51%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	92.88%	94.73%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	91.43%	95.64%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.65%	99.15%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.92%	96.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.07%	86.92%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.64%	85.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.22%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.34%	97.09%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	86.03%	95.78%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.86%	95.56%
CHEMBL242	Q92731	Estrogen receptor beta	84.24%	98.35%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.98%	95.89%
CHEMBL3714130	P46095	G-protein coupled receptor 6	82.83%	97.36%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.01%	90.71%

Plants that contains it

• Aconitum japonicum subsp. subcuneatum
• Asplenium bulbiferum
• Castanea dentata
• Chenopodium murale
• Elaphoglossum lindbergii
• Ferula ammoniacum
• Leucocarpus perfoliatus
• Myrsine melanophloeos
• Pistacia atlantica
• Rogeria adenophylla
• Scrophularia buergeriana
• Stemodia maritima
• Trifolium hybridum

Cross-Links

• PubChem: 90795788
• NPASS: NPC225703
• LOTUS: LTS0207029
• wikiData: Q104252937