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

Details

• Internal ID: fec24989-04e5-439f-9c54-c1a739a3a23d
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: 5-hydroxy-2-(4-methoxyphenoxy)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): COC1=CC=C(C=C1)OC2=CC(=O)C3=C(C=C(C=C3O2)OC4C(C(C(C(O4)CO)O)O)O)O
• SMILES (Isomeric): COC1=CC=C(C=C1)OC2=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/C22H22O11/c1-29-10-2-4-11(5-3-10)30-17-8-14(25)18-13(24)6-12(7-15(18)32-17)31-22-21(28)20(27)19(26)16(9-23)33-22/h2-8,16,19-24,26-28H,9H2,1H3/t16-,19-,20+,21-,22-/m1/s1
• InChI Key: OIQZTOOLPDEEEQ-RECXWPGBSA-N
• Popularity: 2 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): 164.00 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 0.48
• H-Bond Acceptor: 11
• H-Bond Donor: 5
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6078	60.78%
Caco-2	-	0.8713	87.13%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.5812	58.12%
OATP2B1 inhibitior	-	0.5452	54.52%
OATP1B1 inhibitior	+	0.9272	92.72%
OATP1B3 inhibitior	+	0.9777	97.77%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.6102	61.02%
P-glycoprotein inhibitior	-	0.7398	73.98%
P-glycoprotein substrate	-	0.7757	77.57%
CYP3A4 substrate	+	0.5961	59.61%
CYP2C9 substrate	-	0.8389	83.89%
CYP2D6 substrate	-	0.8503	85.03%
CYP3A4 inhibition	-	0.9235	92.35%
CYP2C9 inhibition	-	0.9455	94.55%
CYP2C19 inhibition	-	0.9300	93.00%
CYP2D6 inhibition	-	0.9277	92.77%
CYP1A2 inhibition	-	0.9096	90.96%
CYP2C8 inhibition	-	0.5590	55.90%
CYP inhibitory promiscuity	-	0.8283	82.83%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6386	63.86%
Eye corrosion	-	0.9882	98.82%
Eye irritation	-	0.8782	87.82%
Skin irritation	-	0.8188	81.88%
Skin corrosion	-	0.9671	96.71%
Ames mutagenesis	+	0.6736	67.36%
Human Ether-a-go-go-Related Gene inhibition	-	0.5189	51.89%
Micronuclear	+	0.5833	58.33%
Hepatotoxicity	-	0.8659	86.59%
skin sensitisation	-	0.9284	92.84%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.6799	67.99%
Acute Oral Toxicity (c)	III	0.7427	74.27%
Estrogen receptor binding	+	0.7433	74.33%
Androgen receptor binding	+	0.7245	72.45%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.6414	64.14%
Aromatase binding	+	0.6292	62.92%
PPAR gamma	+	0.8085	80.85%
Honey bee toxicity	-	0.8153	81.53%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	-	0.4202	42.02%

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	99.38%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.32%	85.14%
CHEMBL1951	P21397	Monoamine oxidase A	95.96%	91.49%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.28%	94.00%
CHEMBL220	P22303	Acetylcholinesterase	94.47%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.97%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.91%	96.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.64%	99.15%
CHEMBL2581	P07339	Cathepsin D	91.47%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	91.22%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.45%	94.45%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.77%	86.92%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.98%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.94%	97.09%
CHEMBL4208	P20618	Proteasome component C5	88.04%	90.00%
CHEMBL3194	P02766	Transthyretin	86.18%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.88%	89.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	83.55%	96.21%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.51%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.92%	95.89%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.50%	95.89%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.02%	97.36%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.78%	99.23%

Plants that contains it

• Artemisia rupestris

Cross-Links

• PubChem: 101552465
• LOTUS: LTS0159195
• wikiData: Q105192693