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

Details

• Internal ID: 994280c2-e357-4a51-9350-db08e3669b51
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides
• IUPAC Name: 3,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): COC1=C(C=CC(=C1)C2=C(C(=O)C3=C(O2)C=C(C=C3OC4C(C(C(C(O4)CO)O)O)O)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)C2=C(C(=O)C3=C(O2)C=C(C=C3O[C@@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O)O
• InChI: InChI=1S/C22H22O12/c1-31-11-4-8(2-3-10(11)25)21-19(29)17(27)15-12(32-21)5-9(24)6-13(15)33-22-20(30)18(28)16(26)14(7-23)34-22/h2-6,14,16,18,20,22-26,28-30H,7H2,1H3/t14-,16-,18+,20-,22+/m1/s1
• InChI Key: SEWSFPXRFAJLGT-YTVDIXBESA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₂O₁₂
• Molecular Weight: 478.40 g/mol
• Exact Mass: 478.11112613 g/mol
• Topological Polar Surface Area (TPSA): 196.00 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): -0.24
• H-Bond Acceptor: 12
• H-Bond Donor: 7
• 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	-	0.9291	92.91%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.6190	61.90%
OATP2B1 inhibitior	+	0.5910	59.10%
OATP1B1 inhibitior	+	0.9038	90.38%
OATP1B3 inhibitior	+	0.9740	97.40%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.5753	57.53%
P-glycoprotein inhibitior	-	0.5923	59.23%
P-glycoprotein substrate	-	0.6511	65.11%
CYP3A4 substrate	+	0.6287	62.87%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8324	83.24%
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	+	0.8636	86.36%
CYP inhibitory promiscuity	-	0.7292	72.92%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6890	68.90%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.8863	88.63%
Skin irritation	-	0.8153	81.53%
Skin corrosion	-	0.9600	96.00%
Ames mutagenesis	-	0.5128	51.28%
Human Ether-a-go-go-Related Gene inhibition	-	0.4032	40.32%
Micronuclear	+	0.6633	66.33%
Hepatotoxicity	-	0.6573	65.73%
skin sensitisation	-	0.9373	93.73%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.8569	85.69%
Acute Oral Toxicity (c)	III	0.6624	66.24%
Estrogen receptor binding	+	0.8231	82.31%
Androgen receptor binding	+	0.6186	61.86%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.6257	62.57%
Aromatase binding	+	0.6276	62.76%
PPAR gamma	+	0.7235	72.35%
Honey bee toxicity	-	0.7762	77.62%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5849	58.49%
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	99.51%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.08%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.94%	89.00%
CHEMBL2581	P07339	Cathepsin D	95.24%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.84%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.99%	86.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.86%	99.15%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.28%	95.56%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.85%	86.92%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.38%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	89.32%	94.73%
CHEMBL3194	P02766	Transthyretin	87.53%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.83%	94.45%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	86.67%	95.64%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.07%	90.71%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	82.96%	95.78%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.37%	95.89%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.02%	85.14%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.90%	96.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.07%	97.36%
CHEMBL2424	Q04760	Glyoxalase I	80.35%	91.67%

Plants that contains it

• Artemisia capillaris

Cross-Links

• PubChem: 162845920
• LOTUS: LTS0270938
• wikiData: Q105251583