2-(4-Hydroxyphenyl)-5-hydroxy-3-(2-O-beta-D-glucopyranosyl-beta-D-galactopyranosyloxy)-7-(beta-D-glucopyranosyloxy)-4H-1-benzopyran-4-one

Details

• Internal ID: 1d69acf9-ccf3-4723-a1c1-2a16fd77969b
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 3-[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-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)OC6C(C(C(C(O6)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[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)O
• InChI: InChI=1S/C33H40O21/c34-7-15-19(39)23(43)26(46)31(50-15)48-12-5-13(38)18-14(6-12)49-28(10-1-3-11(37)4-2-10)29(22(18)42)53-33-30(25(45)21(41)17(9-36)52-33)54-32-27(47)24(44)20(40)16(8-35)51-32/h1-6,15-17,19-21,23-27,30-41,43-47H,7-9H2/t15-,16-,17-,19-,20-,21+,23+,24+,25+,26-,27-,30-,31-,32+,33+/m1/s1
• InChI Key: MBFNAZBJKVFNKZ-ULPOSSGFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₄₀O₂₁
• Molecular Weight: 772.70 g/mol
• Exact Mass: 772.20620828 g/mol
• Topological Polar Surface Area (TPSA): 345.00 Ų
• XlogP: -2.70
• Atomic LogP (AlogP): -4.95
• H-Bond Acceptor: 21
• H-Bond Donor: 13
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5736	57.36%
Caco-2	-	0.9139	91.39%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.5848	58.48%
OATP2B1 inhibitior	-	0.7062	70.62%
OATP1B1 inhibitior	+	0.9271	92.71%
OATP1B3 inhibitior	+	0.9434	94.34%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.7593	75.93%
P-glycoprotein inhibitior	+	0.5725	57.25%
P-glycoprotein substrate	-	0.7066	70.66%
CYP3A4 substrate	+	0.6434	64.34%
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	+	0.7778	77.78%
CYP inhibitory promiscuity	-	0.7526	75.26%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6848	68.48%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.8955	89.55%
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	+	0.7422	74.22%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.7446	74.46%
skin sensitisation	-	0.9132	91.32%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.7921	79.21%
Acute Oral Toxicity (c)	IV	0.4763	47.63%
Estrogen receptor binding	+	0.7826	78.26%
Androgen receptor binding	+	0.6704	67.04%
Thyroid receptor binding	-	0.5077	50.77%
Glucocorticoid receptor binding	-	0.6837	68.37%
Aromatase binding	+	0.5441	54.41%
PPAR gamma	+	0.7563	75.63%
Honey bee toxicity	-	0.6886	68.86%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5450	54.50%
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	99.34%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.82%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.58%	94.00%
CHEMBL1951	P21397	Monoamine oxidase A	95.05%	91.49%
CHEMBL2581	P07339	Cathepsin D	95.00%	98.95%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	93.17%	95.64%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.76%	99.15%
CHEMBL3401	O75469	Pregnane X receptor	90.15%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.94%	94.45%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	88.76%	86.92%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	88.14%	95.78%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.92%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.06%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.69%	97.09%
CHEMBL3194	P02766	Transthyretin	85.19%	90.71%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.73%	85.14%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	84.09%	96.21%
CHEMBL242	Q92731	Estrogen receptor beta	83.84%	98.35%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.90%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.70%	96.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.50%	95.89%

Plants that contains it

• Croton megistocarpus
• Geranium sibiricum
• Lagerstroemia indica
• Machilus japonica
• Mimosa pudica
• Scopolia carniolica
• Senecio isatideus
• Strobilanthes cusia
• Trigonella foenum-graecum

Cross-Links

• PubChem: 12960461
• NPASS: NPC132904
• LOTUS: LTS0160330
• wikiData: Q105160712