(2S)-5,8-dihydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3-dihydrochromen-4-one

Details

• Internal ID: dd237878-c7d1-4827-b567-bb3f90b996e8
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: (2S)-5,8-dihydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3-dihydrochromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2=C(C3=C(C(=O)CC(O3)C4=CC=C(C=C4)O)C(=C2)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=C(C3=C(C(=O)C[C@H](O3)C4=CC=C(C=C4)O)C(=C2)O)O)O)O)O
• InChI: InChI=1S/C21H22O10/c1-8-16(25)18(27)19(28)21(29-8)31-14-7-12(24)15-11(23)6-13(30-20(15)17(14)26)9-2-4-10(22)5-3-9/h2-5,7-8,13,16,18-19,21-22,24-28H,6H2,1H3/t8-,13-,16-,18+,19+,21-/m0/s1
• InChI Key: ZIWPWLNTWQUYLO-PUXPQLBMSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₂O₁₀
• Molecular Weight: 434.40 g/mol
• Exact Mass: 434.12129689 g/mol
• Topological Polar Surface Area (TPSA): 166.00 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 0.72
• H-Bond Acceptor: 10
• H-Bond Donor: 6
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6824	68.24%
Caco-2	-	0.8514	85.14%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7206	72.06%
OATP2B1 inhibitior	-	0.5622	56.22%
OATP1B1 inhibitior	+	0.8886	88.86%
OATP1B3 inhibitior	+	0.9528	95.28%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.6361	63.61%
P-glycoprotein inhibitior	-	0.7632	76.32%
P-glycoprotein substrate	-	0.7718	77.18%
CYP3A4 substrate	+	0.6065	60.65%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8428	84.28%
CYP3A4 inhibition	-	0.7058	70.58%
CYP2C9 inhibition	-	0.7346	73.46%
CYP2C19 inhibition	-	0.7984	79.84%
CYP2D6 inhibition	-	0.8690	86.90%
CYP1A2 inhibition	-	0.6207	62.07%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	-	0.6477	64.77%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5639	56.39%
Eye corrosion	-	0.9914	99.14%
Eye irritation	-	0.8349	83.49%
Skin irritation	-	0.6919	69.19%
Skin corrosion	-	0.9347	93.47%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4449	44.49%
Micronuclear	+	0.8559	85.59%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.9017	90.17%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.5512	55.12%
Acute Oral Toxicity (c)	III	0.4772	47.72%
Estrogen receptor binding	+	0.6961	69.61%
Androgen receptor binding	+	0.5348	53.48%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.6993	69.93%
Aromatase binding	+	0.5905	59.05%
PPAR gamma	+	0.7164	71.64%
Honey bee toxicity	-	0.7800	78.00%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5149	51.49%
Fish aquatic toxicity	+	0.9011	90.11%

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	98.97%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.22%	89.00%
CHEMBL2581	P07339	Cathepsin D	95.07%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.36%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.21%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.83%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.68%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.93%	97.09%
CHEMBL4208	P20618	Proteasome component C5	88.58%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.30%	95.89%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	87.09%	90.71%
CHEMBL3401	O75469	Pregnane X receptor	86.96%	94.73%
CHEMBL1951	P21397	Monoamine oxidase A	86.32%	91.49%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	86.23%	95.64%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.69%	95.89%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	85.28%	95.78%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.16%	99.17%
CHEMBL3194	P02766	Transthyretin	83.55%	90.71%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.75%	96.21%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.70%	99.23%
CHEMBL3714130	P46095	G-protein coupled receptor 6	82.14%	97.36%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.46%	85.14%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.54%	99.15%

Plants that contains it

• Spartium junceum

Cross-Links

• PubChem: 162855611
• LOTUS: LTS0182483
• wikiData: Q105377628