3-hydroxy-5-methoxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one

Details

• Internal ID: 32b09603-7e3b-436e-906c-86d93c746ca3
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 3-hydroxy-5-methoxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one
• SMILES (Canonical): COC1=CC(=CC2=C1C(=O)C(=C(O2)C3=CC(=C(C(=C3)O)O)O)O)OC4C(C(C(C(O4)CO)O)O)O
• SMILES (Isomeric): COC1=CC(=CC2=C1C(=O)C(=C(O2)C3=CC(=C(C(=C3)O)O)O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O
• InChI: InChI=1S/C22H22O13/c1-32-11-4-8(33-22-20(31)18(29)16(27)13(6-23)35-22)5-12-14(11)17(28)19(30)21(34-12)7-2-9(24)15(26)10(25)3-7/h2-5,13,16,18,20,22-27,29-31H,6H2,1H3/t13-,16-,18+,20-,22-/m1/s1
• InChI Key: ADZVQTOLVGOLAN-ROSPJSJWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₂O₁₃
• Molecular Weight: 494.40 g/mol
• Exact Mass: 494.10604075 g/mol
• Topological Polar Surface Area (TPSA): 216.00 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): -0.53
• H-Bond Acceptor: 13
• H-Bond Donor: 8
• 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	-	0.9121	91.21%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6190	61.90%
OATP2B1 inhibitior	+	0.5849	58.49%
OATP1B1 inhibitior	+	0.9137	91.37%
OATP1B3 inhibitior	+	0.9740	97.40%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.7565	75.65%
P-glycoprotein inhibitior	-	0.5998	59.98%
P-glycoprotein substrate	-	0.6236	62.36%
CYP3A4 substrate	+	0.6049	60.49%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8359	83.59%
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	+	0.6806	68.06%
CYP inhibitory promiscuity	-	0.7292	72.92%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6890	68.90%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.8981	89.81%
Skin irritation	-	0.8153	81.53%
Skin corrosion	-	0.9600	96.00%
Ames mutagenesis	+	0.6036	60.36%
Human Ether-a-go-go-Related Gene inhibition	-	0.4195	41.95%
Micronuclear	+	0.6633	66.33%
Hepatotoxicity	-	0.7948	79.48%
skin sensitisation	-	0.9373	93.73%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.8757	87.57%
Acute Oral Toxicity (c)	III	0.6624	66.24%
Estrogen receptor binding	+	0.7848	78.48%
Androgen receptor binding	+	0.5950	59.50%
Thyroid receptor binding	+	0.5471	54.71%
Glucocorticoid receptor binding	+	0.6823	68.23%
Aromatase binding	-	0.5297	52.97%
PPAR gamma	+	0.7235	72.35%
Honey bee toxicity	-	0.7786	77.86%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5949	59.49%
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	99.77%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.57%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.95%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.27%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.91%	85.14%
CHEMBL2581	P07339	Cathepsin D	92.88%	98.95%
CHEMBL3714130	P46095	G-protein coupled receptor 6	92.82%	97.36%
CHEMBL3401	O75469	Pregnane X receptor	89.94%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.75%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.51%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.77%	96.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.39%	99.15%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.06%	99.17%
CHEMBL2424	Q04760	Glyoxalase I	85.71%	91.67%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.44%	92.62%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.33%	86.92%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.79%	95.89%
CHEMBL3194	P02766	Transthyretin	83.35%	90.71%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	82.92%	95.64%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.82%	97.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.35%	92.94%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.47%	90.71%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	80.16%	96.21%

Plants that contains it

• Cassiope lycopodioides

Cross-Links

• PubChem: 163103329
• LOTUS: LTS0207881
• wikiData: Q104909909