5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-7-[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one

Details

• Internal ID: d16a10db-76dc-4db8-9a18-ac7f0d7a206c
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-7-[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): COC1=C(C=CC(=C1)C2=CC(=O)C3=C(C=C(C=C3O2)OC4C(C(C(C(O4)CO)O)O)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)C2=CC(=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
• InChI: InChI=1S/C22H22O11/c1-30-15-4-9(2-3-11(15)24)14-7-13(26)18-12(25)5-10(6-16(18)32-14)31-22-21(29)20(28)19(27)17(8-23)33-22/h2-7,17,19-25,27-29H,8H2,1H3/t17-,19+,20-,21+,22+/m0/s1
• InChI Key: GAMYVSCDDLXAQW-AOIWZFSPSA-N
• Popularity: 10 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₂O₁₁
• Molecular Weight: 462.40 g/mol
• Exact Mass: 462.11621151 g/mol
• Topological Polar Surface Area (TPSA): 175.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 0.06
• H-Bond Acceptor: 11
• H-Bond Donor: 6
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4855	48.55%
Caco-2	-	0.9135	91.35%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.6190	61.90%
OATP2B1 inhibitior	+	0.5923	59.23%
OATP1B1 inhibitior	+	0.9414	94.14%
OATP1B3 inhibitior	+	0.9740	97.40%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.5675	56.75%
P-glycoprotein inhibitior	-	0.6943	69.43%
P-glycoprotein substrate	-	0.6586	65.86%
CYP3A4 substrate	+	0.5686	56.86%
CYP2C9 substrate	-	0.8485	84.85%
CYP2D6 substrate	-	0.8501	85.01%
CYP3A4 inhibition	-	0.9108	91.08%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9173	91.73%
CYP2D6 inhibition	-	0.9514	95.14%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	+	0.7357	73.57%
CYP inhibitory promiscuity	-	0.7292	72.92%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6890	68.90%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9097	90.97%
Skin irritation	-	0.8153	81.53%
Skin corrosion	-	0.9600	96.00%
Ames mutagenesis	-	0.5092	50.92%
Human Ether-a-go-go-Related Gene inhibition	-	0.4197	41.97%
Micronuclear	+	0.6633	66.33%
Hepatotoxicity	-	0.9000	90.00%
skin sensitisation	-	0.9373	93.73%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.8016	80.16%
Acute Oral Toxicity (c)	III	0.6624	66.24%
Estrogen receptor binding	+	0.7957	79.57%
Androgen receptor binding	+	0.6202	62.02%
Thyroid receptor binding	+	0.5226	52.26%
Glucocorticoid receptor binding	+	0.6116	61.16%
Aromatase binding	+	0.6424	64.24%
PPAR gamma	+	0.7867	78.67%
Honey bee toxicity	-	0.7220	72.20%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6549	65.49%
Fish aquatic toxicity	+	0.7079	70.79%

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	99.15%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.39%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.20%	85.14%
CHEMBL2581	P07339	Cathepsin D	94.91%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.16%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	94.12%	99.15%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.57%	96.09%
CHEMBL220	P22303	Acetylcholinesterase	91.72%	94.45%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	91.50%	86.92%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.05%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.79%	95.56%
CHEMBL3194	P02766	Transthyretin	88.71%	90.71%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	88.17%	96.21%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.33%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	86.77%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.08%	97.09%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	84.97%	95.78%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.93%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.44%	94.45%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.97%	90.71%
CHEMBL3714130	P46095	G-protein coupled receptor 6	82.95%	97.36%
CHEMBL1907	P15144	Aminopeptidase N	81.74%	93.31%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.39%	96.00%

Plants that contains it

• Apium graveolens
• Commelina communis
• Dioscorea oppositifolia
• Echinops ritro
• Salvia palaestina
• Saussurea medusa
• Stachys alopecuros

Cross-Links

• PubChem: 154496342
• LOTUS: LTS0269750
• wikiData: Q105005484