Taxifolin 7-glucoside

Details

• Internal ID: 8c0f8166-bfa8-4f07-92d3-95f14bd82089
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: (2R,3R)-2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one
• SMILES (Canonical): C1=CC(=C(C=C1C2C(C(=O)C3=C(C=C(C=C3O2)OC4C(C(C(C(O4)CO)O)O)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1[C@@H]2[C@H](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)O)O
• InChI: InChI=1S/C21H22O12/c22-6-13-15(26)17(28)19(30)21(33-13)31-8-4-11(25)14-12(5-8)32-20(18(29)16(14)27)7-1-2-9(23)10(24)3-7/h1-5,13,15,17-26,28-30H,6H2/t13-,15-,17+,18+,19-,20-,21-/m1/s1
• InChI Key: BJAHHJOBSKZTFE-JUIPTLLLSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₂O₁₂
• Molecular Weight: 466.40 g/mol
• Exact Mass: 466.11112613 g/mol
• Topological Polar Surface Area (TPSA): 207.00 Ų
• XlogP: -0.30
• Atomic LogP (AlogP): -1.34
• H-Bond Acceptor: 12
• H-Bond Donor: 8
• Rotatable Bonds: 4

Synonyms

• Taxifolin 7-O-glucoside
• 14292-40-1
• Dihydroquercetin 7-glucoside
• UNII-743G7JDN9T
• Taxifolin-7-O-beta-glucoside
• 743G7JDN9T
• Taxifolin 7-O-|A-D-glucoside
• Taxifolin 7-O-beta-D-glucopyranoside
• TAXIFOLIN 7-O-BETA-D-GLUCOSIDE
• (2R,3R)-2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one
• Flavanone, 3,3',4',5,7-pentahydroxy-, 7-beta-D-glucopyranoside
• 4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-7-(beta-D-glucopyranosyloxy)-2,3-dihydro-3,5-dihydroxy-, (2R,3R)-
• 4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-7-(beta-D-glucopyranosyloxy)-2,3-dihydro-3,5-dihydroxy-, (2R-trans)-
• CHEMBL4648019
• Taxifolin 7-O-??-D-glucoside
• DTXSID70162220
• HY-N7681
• AKOS040763789
• TAXIFOLIN-7-O-.BETA.-GLUCOSIDE
• MS-28590
• CS-0135198
• E80616
• TAXIFOLIN 7-O-.BETA.-D-GLUCOPYRANOSIDE
• Q27266231
• FLAVANONE, 3,3',4',5,7-PENTAHYDROXY-, 7-.BETA.-D-GLUCOPYRANOSIDE
• 4H-1-BENZOPYRAN-4-ONE, 2-(3,4-DIHYDROXYPHENYL)-7-(.BETA.-D-GLUCOPYRANOSYLOXY)-2,3-DIHYDRO-3,5-DIHYDROXY-, (2R,3R)-
• 4H-1-BENZOPYRAN-4-ONE, 2-(3,4-DIHYDROXYPHENYL)-7-(.BETA.-D-GLUCOPYRANOSYLOXY)-2,3-DIHYDRO-3,5-DIHYDROXY-, (2R-TRANS)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5116	51.16%
Caco-2	-	0.9419	94.19%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.6068	60.68%
OATP2B1 inhibitior	+	0.5769	57.69%
OATP1B1 inhibitior	+	0.9463	94.63%
OATP1B3 inhibitior	+	0.9265	92.65%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.4512	45.12%
P-glycoprotein inhibitior	-	0.7586	75.86%
P-glycoprotein substrate	-	0.9255	92.55%
CYP3A4 substrate	+	0.5795	57.95%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8522	85.22%
CYP3A4 inhibition	-	0.9193	91.93%
CYP2C9 inhibition	-	0.9296	92.96%
CYP2C19 inhibition	-	0.9289	92.89%
CYP2D6 inhibition	-	0.9513	95.13%
CYP1A2 inhibition	-	0.9084	90.84%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	-	0.7728	77.28%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7144	71.44%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.8167	81.67%
Skin irritation	-	0.8036	80.36%
Skin corrosion	-	0.9691	96.91%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4372	43.72%
Micronuclear	+	0.6533	65.33%
Hepatotoxicity	-	0.8250	82.50%
skin sensitisation	-	0.9122	91.22%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	+	0.5354	53.54%
Acute Oral Toxicity (c)	III	0.4045	40.45%
Estrogen receptor binding	+	0.6325	63.25%
Androgen receptor binding	-	0.4819	48.19%
Thyroid receptor binding	+	0.6176	61.76%
Glucocorticoid receptor binding	-	0.5274	52.74%
Aromatase binding	+	0.5208	52.08%
PPAR gamma	+	0.6973	69.73%
Honey bee toxicity	-	0.7428	74.28%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5850	58.50%
Fish aquatic toxicity	+	0.8218	82.18%

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	99.45%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	94.88%	91.49%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.66%	99.15%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.86%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	91.94%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.50%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.99%	89.00%
CHEMBL2581	P07339	Cathepsin D	88.72%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.34%	95.56%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.66%	86.92%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.04%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.56%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.41%	94.45%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	85.14%	96.21%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.76%	99.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.49%	99.23%

Plants that contains it

• Alcea rosea
• Allium cepa
• Alpinia roxburghii
• Balanops australiana
• Coleogyne ramosissima
• Cuscuta reflexa
• Davallia perdurans
• Euonymus tingens
• Euphorbia cornigera
• Fissistigma oldhamii
• Gonzalezia decurrens
• Hylocomium splendens
• Kokoona reflexa
• Lycium chinense
• Maesa ramentacea
• Millettia laurentii
• Monodora tenuifolia
• Ocimum tenuiflorum
• Pelargonium reniforme
• Picea abies
• Pinus strobus
• Pinus sylvestris
• Pluchea odorata
• Podocarpus nivalis
• Pseudotsuga menziesii
• Salacia lehmbachii
• Salvia yosgadensis
• Sideritis brevibracteata
• Sideroxylon cubense
• Sorghum bicolor

Cross-Links

• PubChem: 14282775
• NPASS: NPC163191
• LOTUS: LTS0133999
• wikiData: Q27266231