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

Details

• Internal ID: e0629c48-22b6-4f8c-87cc-e80bed5728b9
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 5,6-dihydroxy-2-(4-methoxyphenyl)-7-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2=C(C(=C3C(=C2)OC(=CC3=O)C4=CC=C(C=C4)OC)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=C(C(=C3C(=C2)OC(=CC3=O)C4=CC=C(C=C4)OC)O)O)O)O)O
• InChI: InChI=1S/C22H22O10/c1-9-17(24)20(27)21(28)22(30-9)32-15-8-14-16(19(26)18(15)25)12(23)7-13(31-14)10-3-5-11(29-2)6-4-10/h3-9,17,20-22,24-28H,1-2H3/t9-,17-,20+,21+,22-/m0/s1
• InChI Key: QTRQFPKFQLMVKS-DKOLOVBJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₂O₁₀
• Molecular Weight: 446.40 g/mol
• Exact Mass: 446.12129689 g/mol
• Topological Polar Surface Area (TPSA): 155.00 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 1.09
• H-Bond Acceptor: 10
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7980	79.80%
Caco-2	-	0.7976	79.76%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6676	66.76%
OATP2B1 inhibitior	-	0.5365	53.65%
OATP1B1 inhibitior	+	0.7462	74.62%
OATP1B3 inhibitior	+	0.9220	92.20%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.7237	72.37%
P-glycoprotein inhibitior	-	0.5960	59.60%
P-glycoprotein substrate	-	0.6307	63.07%
CYP3A4 substrate	+	0.6125	61.25%
CYP2C9 substrate	-	0.7502	75.02%
CYP2D6 substrate	-	0.8538	85.38%
CYP3A4 inhibition	-	0.6056	60.56%
CYP2C9 inhibition	-	0.9236	92.36%
CYP2C19 inhibition	-	0.8201	82.01%
CYP2D6 inhibition	-	0.8906	89.06%
CYP1A2 inhibition	-	0.7268	72.68%
CYP2C8 inhibition	+	0.6641	66.41%
CYP inhibitory promiscuity	-	0.5508	55.08%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6071	60.71%
Eye corrosion	-	0.9840	98.40%
Eye irritation	-	0.8657	86.57%
Skin irritation	-	0.6906	69.06%
Skin corrosion	-	0.9434	94.34%
Ames mutagenesis	-	0.5264	52.64%
Human Ether-a-go-go-Related Gene inhibition	-	0.4792	47.92%
Micronuclear	+	0.9200	92.00%
Hepatotoxicity	-	0.8375	83.75%
skin sensitisation	-	0.9206	92.06%
Respiratory toxicity	-	0.6556	65.56%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.9223	92.23%
Acute Oral Toxicity (c)	III	0.4825	48.25%
Estrogen receptor binding	+	0.8133	81.33%
Androgen receptor binding	+	0.7736	77.36%
Thyroid receptor binding	+	0.5485	54.85%
Glucocorticoid receptor binding	+	0.7371	73.71%
Aromatase binding	+	0.6510	65.10%
PPAR gamma	+	0.7595	75.95%
Honey bee toxicity	-	0.7727	77.27%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5549	55.49%
Fish aquatic toxicity	+	0.9150	91.50%

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	99.22%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	98.12%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.40%	85.14%
CHEMBL2581	P07339	Cathepsin D	96.52%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.91%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.74%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	92.52%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.75%	95.56%
CHEMBL3714130	P46095	G-protein coupled receptor 6	89.60%	97.36%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.14%	86.92%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	89.03%	90.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.95%	99.15%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	88.53%	95.89%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.23%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.62%	99.17%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	85.80%	81.11%
CHEMBL3401	O75469	Pregnane X receptor	84.69%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.38%	96.09%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	84.29%	96.21%
CHEMBL4208	P20618	Proteasome component C5	82.02%	90.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	80.79%	96.77%
CHEMBL3194	P02766	Transthyretin	80.39%	90.71%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	80.24%	87.67%

Plants that contains it

• Linaria aeruginea

Cross-Links

• PubChem: 59991331
• LOTUS: LTS0105448
• wikiData: Q105227888