Taxifolin 3'-glucoside

Details

• Internal ID: 87ca8914-d11d-4482-844b-0f3e73e0ff6d
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides
• IUPAC Name: (2R,3R)-3,5,7-trihydroxy-2-[4-hydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-2,3-dihydrochromen-4-one
• SMILES (Canonical): C1=CC(=C(C=C1C2C(C(=O)C3=C(C=C(C=C3O2)O)O)O)OC4C(C(C(C(O4)CO)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)O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O
• InChI: InChI=1S/C21H22O12/c22-6-13-15(26)17(28)19(30)21(33-13)32-11-3-7(1-2-9(11)24)20-18(29)16(27)14-10(25)4-8(23)5-12(14)31-20/h1-5,13,15,17-26,28-30H,6H2/t13-,15-,17+,18+,19-,20-,21-/m1/s1
• InChI Key: CZOXIGOPZRIBJM-JUIPTLLLSA-N
• Popularity: 0 references 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 3'-O-glucoside
• 31106-05-5
• Dihydroquercetin 3'-glucoside
• UNII-779OJU5O9Q
• 779OJU5O9Q
• Taxifolin 3'-O-beta-D-glucopyranoside
• (2R,3R)-3,5,7-trihydroxy-2-[4-hydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-2,3-dihydrochromen-4-one
• Flavanone, 3,3',4',5,7-pentahydroxy-, 3'-beta-D-glucopyranoside
• 4H-1-Benzopyran-4-one, 2-(3-(beta-D-glucopyranosyloxy)-4-hydroxyphenyl)-2,3-dihydro-3,5,7-trihydroxy-, (2R,3R)-
• 4H-1-Benzopyran-4-one, 2-(3-(beta-D-glucopyranosyloxy)-4-hydroxyphenyl)-2,3-dihydro-3,5,7-trihydroxy-, (2R-trans)-
• Taxifolin 3/'-glucoside
• MEGxp0_000740
• SCHEMBL3776571
• DTXSID20185045
• AKOS040762404
• TAXIFOLIN 3'-O-.BETA.-D-GLUCOPYRANOSIDE
• Q27266570
• FLAVANONE, 3,3',4',5,7-PENTAHYDROXY-, 3'-.BETA.-D-GLUCOPYRANOSIDE
• 4H-1-BENZOPYRAN-4-ONE, 2-(3-(.BETA.-D-GLUCOPYRANOSYLOXY)-4-HYDROXYPHENYL)-2,3-DIHYDRO-3,5,7-TRIHYDROXY-, (2R,3R)-
• 4H-1-BENZOPYRAN-4-ONE, 2-(3-(.BETA.-D-GLUCOPYRANOSYLOXY)-4-HYDROXYPHENYL)-2,3-DIHYDRO-3,5,7-TRIHYDROXY-, (2R-TRANS)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5116	51.16%
Caco-2	-	0.9301	93.01%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.6068	60.68%
OATP2B1 inhibitior	+	0.5794	57.94%
OATP1B1 inhibitior	+	0.9324	93.24%
OATP1B3 inhibitior	+	0.9265	92.65%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.4754	47.54%
P-glycoprotein inhibitior	-	0.6815	68.15%
P-glycoprotein substrate	-	0.9077	90.77%
CYP3A4 substrate	+	0.5727	57.27%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8512	85.12%
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	+	0.5250	52.50%
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	-	0.8091	80.91%
Skin irritation	-	0.8036	80.36%
Skin corrosion	-	0.9691	96.91%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4885	48.85%
Micronuclear	+	0.6533	65.33%
Hepatotoxicity	-	0.6000	60.00%
skin sensitisation	-	0.9122	91.22%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	+	0.5794	57.94%
Acute Oral Toxicity (c)	III	0.4045	40.45%
Estrogen receptor binding	+	0.7420	74.20%
Androgen receptor binding	-	0.5178	51.78%
Thyroid receptor binding	+	0.5955	59.55%
Glucocorticoid receptor binding	+	0.5803	58.03%
Aromatase binding	-	0.4829	48.29%
PPAR gamma	+	0.6788	67.88%
Honey bee toxicity	-	0.7996	79.96%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6650	66.50%
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	99.21%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.94%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.11%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.43%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	90.82%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.66%	97.09%
CHEMBL2581	P07339	Cathepsin D	90.14%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.71%	99.15%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	88.45%	86.92%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.36%	99.17%
CHEMBL3194	P02766	Transthyretin	86.81%	90.71%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	86.15%	96.21%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.85%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.97%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.43%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.91%	99.23%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	81.78%	93.40%

Plants that contains it

• Alcea rosea
• Alpinia roxburghii
• Balanops australiana
• Cedrus deodara
• Davallia perdurans
• Erica cinerea
• Euonymus tingens
• Euphorbia cornigera
• Gonzalezia decurrens
• Hylocomium splendens
• Kokoona reflexa
• Maesa ramentacea
• Millettia laurentii
• Monodora tenuifolia
• Ocimum tenuiflorum
• Picea abies
• Pinus massoniana
• Pinus strobus
• Pinus sylvestris
• Pluchea odorata
• Pseudotsuga menziesii
• Salacia lehmbachii
• Salvia yosgadensis
• Sideritis brevibracteata
• Sideroxylon cubense
• Smilax glabra

Cross-Links

• PubChem: 14282774
• NPASS: NPC100931
• LOTUS: LTS0169742
• wikiData: Q27266570