2-(4-Hydroxyphenyl)-5,7-dihydroxy-6-[2-O-(beta-D-xylopyranosyl)-beta-D-glucopyranosyl]-4H-1-benzopyran-4-one

Details

• Internal ID: d05994db-c5ad-4c8a-95c9-1ffa363d8a2d
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid C-glycosides
• IUPAC Name: 6-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
• SMILES (Canonical): C1C(C(C(C(O1)OC2C(C(C(OC2C3=C(C4=C(C=C3O)OC(=CC4=O)C5=CC=C(C=C5)O)O)CO)O)O)O)O)O
• SMILES (Isomeric): C1[C@H]([C@@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2C3=C(C4=C(C=C3O)OC(=CC4=O)C5=CC=C(C=C5)O)O)CO)O)O)O)O)O
• InChI: InChI=1S/C26H28O14/c27-7-16-20(33)22(35)25(40-26-23(36)19(32)13(31)8-37-26)24(39-16)18-12(30)6-15-17(21(18)34)11(29)5-14(38-15)9-1-3-10(28)4-2-9/h1-6,13,16,19-20,22-28,30-36H,7-8H2/t13-,16-,19+,20-,22+,23-,24+,25-,26+/m1/s1
• InChI Key: ACRIYYKEWCXQOS-XLUFPDOKSA-N
• Popularity: 0 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): 236.00 Ų
• XlogP: -1.30
• Atomic LogP (AlogP): -1.45
• H-Bond Acceptor: 14
• H-Bond Donor: 9
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5110	51.10%
Caco-2	-	0.9319	93.19%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.4988	49.88%
OATP2B1 inhibitior	-	0.5537	55.37%
OATP1B1 inhibitior	+	0.8587	85.87%
OATP1B3 inhibitior	+	0.9174	91.74%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.5262	52.62%
P-glycoprotein inhibitior	-	0.6669	66.69%
P-glycoprotein substrate	-	0.6404	64.04%
CYP3A4 substrate	+	0.6600	66.00%
CYP2C9 substrate	-	0.6643	66.43%
CYP2D6 substrate	-	0.8569	85.69%
CYP3A4 inhibition	-	0.9373	93.73%
CYP2C9 inhibition	-	0.9644	96.44%
CYP2C19 inhibition	-	0.9395	93.95%
CYP2D6 inhibition	-	0.9332	93.32%
CYP1A2 inhibition	-	0.9304	93.04%
CYP2C8 inhibition	+	0.7094	70.94%
CYP inhibitory promiscuity	-	0.8779	87.79%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6882	68.82%
Eye corrosion	-	0.9940	99.40%
Eye irritation	-	0.9071	90.71%
Skin irritation	-	0.8205	82.05%
Skin corrosion	-	0.9667	96.67%
Ames mutagenesis	+	0.6236	62.36%
Human Ether-a-go-go-Related Gene inhibition	-	0.4679	46.79%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.7196	71.96%
skin sensitisation	-	0.9071	90.71%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.9464	94.64%
Acute Oral Toxicity (c)	III	0.4508	45.08%
Estrogen receptor binding	+	0.8155	81.55%
Androgen receptor binding	+	0.7500	75.00%
Thyroid receptor binding	+	0.5551	55.51%
Glucocorticoid receptor binding	+	0.5873	58.73%
Aromatase binding	+	0.7080	70.80%
PPAR gamma	+	0.7977	79.77%
Honey bee toxicity	-	0.6886	68.86%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.7253	72.53%

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	99.80%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.92%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.99%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.66%	94.00%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	94.65%	83.57%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.57%	97.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.22%	99.15%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.61%	86.92%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.56%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.54%	85.14%
CHEMBL1951	P21397	Monoamine oxidase A	87.43%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.32%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.67%	94.45%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	85.18%	80.33%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.00%	95.83%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	84.10%	96.21%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.38%	95.89%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.15%	90.71%
CHEMBL3401	O75469	Pregnane X receptor	82.96%	94.73%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	82.71%	95.78%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	82.32%	91.71%
CHEMBL3194	P02766	Transthyretin	81.44%	90.71%
CHEMBL3922	P50579	Methionine aminopeptidase 2	81.02%	97.28%

Plants that contains it

• Euphorbia hirta
• Flacourtia indica
• Oxalis triangularis
• Tripterospermum japonicum

Cross-Links

• PubChem: 101390322
• NPASS: NPC207741
• LOTUS: LTS0260283
• wikiData: Q104909252