Kaempferol 3,7-diglucoside

Details

• Internal ID: 661385c2-ab99-44fd-96b2-9a09001011d2
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 5-hydroxy-2-(4-hydroxyphenyl)-3,7-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]chromen-4-one
• SMILES (Canonical): C1=CC(=CC=C1C2=C(C(=O)C3=C(C=C(C=C3O2)OC4C(C(C(C(O4)CO)O)O)O)O)OC5C(C(C(C(O5)CO)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O
• InChI: InChI=1S/C27H30O16/c28-7-14-17(32)20(35)22(37)26(41-14)39-11-5-12(31)16-13(6-11)40-24(9-1-3-10(30)4-2-9)25(19(16)34)43-27-23(38)21(36)18(33)15(8-29)42-27/h1-6,14-15,17-18,20-23,26-33,35-38H,7-8H2/t14-,15-,17-,18-,20+,21+,22-,23-,26-,27+/m1/s1
• InChI Key: XFFQVRFGLSBFON-DEFKTLOSSA-N
• Popularity: 8 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀O₁₆
• Molecular Weight: 610.50 g/mol
• Exact Mass: 610.15338487 g/mol
• Topological Polar Surface Area (TPSA): 266.00 Ų
• XlogP: -1.10
• Atomic LogP (AlogP): -2.77
• H-Bond Acceptor: 16
• H-Bond Donor: 10
• Rotatable Bonds: 7

Synonyms

• 25615-14-9
• Kaempferol 3,7-di-O-glucoside
• Paeonoside (C27 glycoside)
• CHEBI:67928
• 1SL009I82F
• Kaempferol-3,7-di-O-|A-glucoside
• Kaempferol-3-O-beta-D-glucosyl-7-O-beta-D-glucoside
• Astragalin 7-O-beta-D-glucopyranoside
• 5-hydroxy-2-(4-hydroxyphenyl)-3,7-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]chromen-4-one
• Kaempferol 3,7-di-eta-D-glucopyranoside
• kaempferol-3-O-beta-D-glucopyranosyl-7-O-beta-D-glucopyranoside
• 4H-1-Benzopyran-4-one, 3,7-bis(beta-D-glucopyranosyloxy)-5-hydroxy-2-(4-hydroxyphenyl)-
• UNII-1SL009I82F
• CHEMBL2206209
• Kaempferol -3,7-di-O-glucoside
• CHEBI:133224
• DTXSID601311270
• HY-N8161
• Kaempferol-3,7-di-O-??-glucoside
• Kaempferol-3,7-di-O-beta-glucoside
• AKOS040761936
• kaempferol 3,7-di-O-beta-D-glucoside
• kaempferol 3,7-bis-O-beta-D-glucoside
• XK172894
• Kaempferol 3,7-O-beta-D-diglucopyranoside
• kaempferol-3,7- di-beta-D-glucopyranoside
• CS-0140225
• E88882
• Glucopyranoside, kaempferol-3,7 di-, beta-D-
• KAEMPFEROL 3,7-DI-.BETA.-D-GLUCOPYRANOSIDE
• KAEMPFEROL 3,7-DI-O-.BETA.-D-GLUCOPYRANOSIDE
• Q27136401
• GLUCOPYRANOSIDE, KAEMPFEROL-3,7 DI-, .BETA.-D-
• KAEMPFEROL-3-O-.BETA.-D-GLUCOSYL-7-O-.BETA.-D-GLUCOSIDE
• 3,7-bis(beta-D-glucopyranosyloxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
• 3-(beta-D-glucopyranosyloxy)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl beta-D-glucopyranoside
• 3-(beta-D-glucopyranosyloxy)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl beta-D-glucopyranoside
• 4H-1-BENZOPYRAN-4-ONE, 3,7-BIS(.BETA.-D-GLUCOPYRANOSYLOXY)-5-HYDROXY-2-(4-HYDROXYPHENYL)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5736	57.36%
Caco-2	-	0.9334	93.34%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.5848	58.48%
OATP2B1 inhibitior	-	0.5510	55.10%
OATP1B1 inhibitior	+	0.9265	92.65%
OATP1B3 inhibitior	+	0.9434	94.34%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.7117	71.17%
P-glycoprotein inhibitior	-	0.5404	54.04%
P-glycoprotein substrate	-	0.8070	80.70%
CYP3A4 substrate	+	0.5979	59.79%
CYP2C9 substrate	-	0.6762	67.62%
CYP2D6 substrate	-	0.8575	85.75%
CYP3A4 inhibition	-	0.9390	93.90%
CYP2C9 inhibition	-	0.9315	93.15%
CYP2C19 inhibition	-	0.9047	90.47%
CYP2D6 inhibition	-	0.9458	94.58%
CYP1A2 inhibition	-	0.9180	91.80%
CYP2C8 inhibition	+	0.7880	78.80%
CYP inhibitory promiscuity	-	0.7526	75.26%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6848	68.48%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.8753	87.53%
Skin irritation	-	0.8255	82.55%
Skin corrosion	-	0.9691	96.91%
Ames mutagenesis	+	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6956	69.56%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.7071	70.71%
skin sensitisation	-	0.9132	91.32%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.7535	75.35%
Acute Oral Toxicity (c)	IV	0.4763	47.63%
Estrogen receptor binding	+	0.7369	73.69%
Androgen receptor binding	+	0.6544	65.44%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.5595	55.95%
Aromatase binding	+	0.5585	55.85%
PPAR gamma	+	0.7211	72.11%
Honey bee toxicity	-	0.7524	75.24%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6050	60.50%
Fish aquatic toxicity	+	0.7958	79.58%

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	99.24%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.43%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.25%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.08%	94.00%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	93.50%	95.64%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.67%	99.15%
CHEMBL3401	O75469	Pregnane X receptor	89.92%	94.73%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.61%	86.92%
CHEMBL1951	P21397	Monoamine oxidase A	89.60%	91.49%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.99%	97.09%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	88.37%	95.78%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.90%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.80%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.53%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.72%	85.14%
CHEMBL3194	P02766	Transthyretin	84.93%	90.71%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.53%	96.09%
CHEMBL242	Q92731	Estrogen receptor beta	83.72%	98.35%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.90%	95.56%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	81.57%	96.21%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.49%	95.89%

Plants that contains it

• Allium macrostemon
• Allium victorialis
• Arabidopsis thaliana
• Aster spathulifolius
• Corydalis bungeana
• Corydalis ochotensis
• Crocus sativus
• Delphinium staphisagria
• Equisetum ramosissimum subsp. debile
• Evolvulus alsinoides
• Helichrysum arenarium
• Heliotropium amplexicaule
• Iberis amara
• Lotus corniculatus
• Lotus polyphyllos
• Maclura cochinchinensis
• Paeonia lactiflora
• Paeonia suffruticosa
• Pelargonium graveolens
• Periploca calophylla
• Prumnopitys ferruginoides
• Sophora tomentosa
• Wisteria floribunda

Cross-Links

• PubChem: 6325460
• NPASS: NPC297987
• ChEMBL: CHEMBL2206209
• LOTUS: LTS0215496
• wikiData: Q23069148