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

Details

• Internal ID: 14fefcaa-2747-44ec-bf10-f11fdf815e62
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 2-(3,4-dihydroxy-5-methoxyphenyl)-5-hydroxy-7-[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): COC1=CC(=CC(=C1O)O)C2=CC(=O)C3=C(C=C(C=C3O2)OC4C(C(C(C(O4)CO)O)O)O)O
• SMILES (Isomeric): COC1=CC(=CC(=C1O)O)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
• InChI: InChI=1S/C22H22O12/c1-31-15-3-8(2-12(26)18(15)27)13-6-11(25)17-10(24)4-9(5-14(17)33-13)32-22-21(30)20(29)19(28)16(7-23)34-22/h2-6,16,19-24,26-30H,7H2,1H3/t16-,19+,20-,21+,22+/m0/s1
• InChI Key: ASGQQIRHJIOWQM-GVJIXFOXSA-N
• Popularity: 0 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: 0.50
• 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	-	0.9105	91.05%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6190	61.90%
OATP2B1 inhibitior	+	0.5898	58.98%
OATP1B1 inhibitior	+	0.9287	92.87%
OATP1B3 inhibitior	+	0.9740	97.40%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.5154	51.54%
P-glycoprotein inhibitior	-	0.6360	63.60%
P-glycoprotein substrate	-	0.5757	57.57%
CYP3A4 substrate	+	0.5791	57.91%
CYP2C9 substrate	-	0.8415	84.15%
CYP2D6 substrate	-	0.8515	85.15%
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	+	0.6849	68.49%
CYP inhibitory promiscuity	-	0.7292	72.92%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6890	68.90%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9099	90.99%
Skin irritation	-	0.8153	81.53%
Skin corrosion	-	0.9600	96.00%
Ames mutagenesis	+	0.5236	52.36%
Human Ether-a-go-go-Related Gene inhibition	+	0.6684	66.84%
Micronuclear	+	0.6633	66.33%
Hepatotoxicity	-	0.8375	83.75%
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	-	0.8365	83.65%
Acute Oral Toxicity (c)	III	0.6624	66.24%
Estrogen receptor binding	+	0.7423	74.23%
Androgen receptor binding	+	0.6194	61.94%
Thyroid receptor binding	+	0.5251	52.51%
Glucocorticoid receptor binding	+	0.5640	56.40%
Aromatase binding	+	0.5281	52.81%
PPAR gamma	+	0.7221	72.21%
Honey bee toxicity	-	0.7313	73.13%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6749	67.49%
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	99.56%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.67%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.59%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.08%	89.00%
CHEMBL2581	P07339	Cathepsin D	92.24%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.03%	96.09%
CHEMBL3194	P02766	Transthyretin	89.99%	90.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.54%	99.15%
CHEMBL3714130	P46095	G-protein coupled receptor 6	89.09%	97.36%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.96%	86.33%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	88.92%	96.21%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.78%	95.56%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	88.51%	86.92%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.45%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	88.22%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.42%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.62%	95.89%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.60%	90.71%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.10%	92.62%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.06%	95.89%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.55%	96.00%

Plants that contains it

• Stachys alopecuros

Cross-Links

• PubChem: 162927562
• LOTUS: LTS0195591
• wikiData: Q104917814