4H-1-Benzopyran-4-one, 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-((2-O-(3,4,5-trihydroxybenzoyl)-beta-D-glucopyranosyl)oxy)-

Details

• Internal ID: 1c0479ba-056d-40d6-9fc1-6bb1d343fcd4
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: [(2S,3R,4S,5S,6R)-2-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] 3,4,5-trihydroxybenzoate
• SMILES (Canonical): C1=CC(=CC=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)OC4C(C(C(C(O4)CO)O)O)OC(=O)C5=CC(=C(C(=C5)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)OC(=O)C5=CC(=C(C(=C5)O)O)O)O
• InChI: InChI=1S/C28H24O15/c29-9-18-21(36)23(38)26(42-27(39)11-5-15(33)20(35)16(34)6-11)28(41-18)43-25-22(37)19-14(32)7-13(31)8-17(19)40-24(25)10-1-3-12(30)4-2-10/h1-8,18,21,23,26,28-36,38H,9H2/t18-,21-,23+,26-,28+/m1/s1
• InChI Key: UWIQWJHBYRTKAL-KQOASZHBSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₂₄O₁₅
• Molecular Weight: 600.50 g/mol
• Exact Mass: 600.11152005 g/mol
• Topological Polar Surface Area (TPSA): 253.00 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 0.74
• H-Bond Acceptor: 15
• H-Bond Donor: 9
• Rotatable Bonds: 6

Synonyms

• CHEMBL444191
• 4H-1-Benzopyran-4-one, 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-((2-O-(3,4,5-trihydroxybenzoyl)-beta-D-glucopyranosyl)oxy)-
• C28H24O15
• C28-H24-O15
• Astragalin 2''-gallate
• D0HC9P
• SCHEMBL12470746
• DTXSID40997708
• BDBM50004199
• PD186083
• kaempferol-3-O-(2''-O-galloyl)-glucoside
• (2S,3R,4S,5S,6R)-2-((5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl)oxy)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl 3,4,5-trihydroxybenzoate
• (2S,3R,4S,5S,6R)-2-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxybenzoate
• 5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-3-yl 2-O-(3,4,5-trihydroxybenzoyl)hexopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6249	62.49%
Caco-2	-	0.9139	91.39%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.5589	55.89%
OATP2B1 inhibitior	+	0.5866	58.66%
OATP1B1 inhibitior	-	0.3261	32.61%
OATP1B3 inhibitior	+	0.9680	96.80%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.7849	78.49%
P-glycoprotein inhibitior	+	0.6938	69.38%
P-glycoprotein substrate	-	0.5549	55.49%
CYP3A4 substrate	+	0.6643	66.43%
CYP2C9 substrate	-	0.6401	64.01%
CYP2D6 substrate	-	0.8662	86.62%
CYP3A4 inhibition	-	0.9184	91.84%
CYP2C9 inhibition	-	0.9174	91.74%
CYP2C19 inhibition	-	0.9299	92.99%
CYP2D6 inhibition	-	0.9641	96.41%
CYP1A2 inhibition	-	0.9320	93.20%
CYP2C8 inhibition	+	0.9016	90.16%
CYP inhibitory promiscuity	-	0.8782	87.82%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7263	72.63%
Eye corrosion	-	0.9928	99.28%
Eye irritation	-	0.8699	86.99%
Skin irritation	-	0.8274	82.74%
Skin corrosion	-	0.9638	96.38%
Ames mutagenesis	+	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8408	84.08%
Micronuclear	+	0.6633	66.33%
Hepatotoxicity	-	0.5321	53.21%
skin sensitisation	-	0.9201	92.01%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.9401	94.01%
Acute Oral Toxicity (c)	IV	0.4205	42.05%
Estrogen receptor binding	+	0.7919	79.19%
Androgen receptor binding	+	0.7963	79.63%
Thyroid receptor binding	+	0.5311	53.11%
Glucocorticoid receptor binding	+	0.6200	62.00%
Aromatase binding	-	0.4912	49.12%
PPAR gamma	+	0.7152	71.52%
Honey bee toxicity	-	0.7806	78.06%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6150	61.50%
Fish aquatic toxicity	+	0.8695	86.95%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2409	P34913	Epoxide hydratase	27430 nM	IC50	PMID: 24679441

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	99.54%	95.64%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.52%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.21%	89.00%
CHEMBL3194	P02766	Transthyretin	96.86%	90.71%
CHEMBL1951	P21397	Monoamine oxidase A	96.38%	91.49%
CHEMBL2581	P07339	Cathepsin D	95.64%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.20%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.75%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.90%	86.33%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	90.94%	95.78%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	87.36%	97.53%
CHEMBL3401	O75469	Pregnane X receptor	87.35%	94.73%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.59%	86.92%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	84.68%	96.21%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.82%	99.15%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.74%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.71%	96.09%
CHEMBL4208	P20618	Proteasome component C5	82.42%	90.00%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	82.09%	83.00%
CHEMBL4530	P00488	Coagulation factor XIII	81.16%	96.00%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	80.63%	94.42%

Plants that contains it

• Acridocarpus vivy
• Euphorbia humifusa
• Euphorbia maculata
• Syneilesis palmata
• Uncaria donisii

Cross-Links

• PubChem: 5488619
• NPASS: NPC61904
• ChEMBL: CHEMBL444191
• LOTUS: LTS0152030
• wikiData: Q82989950