7-[(2S,3R,4R,5S)-3,4-dihydroxy-5-[(1S)-1-hydroxyethyl]oxolan-2-yl]oxy-3,5-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one

Details

• Internal ID: 6ad7ec59-a726-4309-ac81-0ab41dc20f33
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 7-[(2S,3R,4R,5S)-3,4-dihydroxy-5-[(1S)-1-hydroxyethyl]oxolan-2-yl]oxy-3,5-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
• SMILES (Canonical): CC(C1C(C(C(O1)OC2=CC(=C3C(=C2)OC(=C(C3=O)O)C4=CC=C(C=C4)O)O)O)O)O
• SMILES (Isomeric): C[C@@H]([C@H]1[C@@H]([C@H]([C@@H](O1)OC2=CC(=C3C(=C2)OC(=C(C3=O)O)C4=CC=C(C=C4)O)O)O)O)O
• InChI: InChI=1S/C21H20O10/c1-8(22)19-17(27)18(28)21(31-19)29-11-6-12(24)14-13(7-11)30-20(16(26)15(14)25)9-2-4-10(23)5-3-9/h2-8,17-19,21-24,26-28H,1H3/t8-,17+,18+,19-,21+/m0/s1
• InChI Key: PMWOCSJXZDDAPR-RBOMAVFTSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₀O₁₀
• Molecular Weight: 432.40 g/mol
• Exact Mass: 432.10564683 g/mol
• Topological Polar Surface Area (TPSA): 166.00 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 0.78
• H-Bond Acceptor: 10
• H-Bond Donor: 6
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8971	89.71%
Caco-2	-	0.9059	90.59%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7551	75.51%
OATP2B1 inhibitior	+	0.5947	59.47%
OATP1B1 inhibitior	+	0.9074	90.74%
OATP1B3 inhibitior	+	0.9043	90.43%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.8165	81.65%
P-glycoprotein inhibitior	-	0.7032	70.32%
P-glycoprotein substrate	-	0.6072	60.72%
CYP3A4 substrate	+	0.6423	64.23%
CYP2C9 substrate	-	0.7354	73.54%
CYP2D6 substrate	-	0.8607	86.07%
CYP3A4 inhibition	+	0.6047	60.47%
CYP2C9 inhibition	-	0.5983	59.83%
CYP2C19 inhibition	+	0.5408	54.08%
CYP2D6 inhibition	-	0.8550	85.50%
CYP1A2 inhibition	+	0.6219	62.19%
CYP2C8 inhibition	+	0.7765	77.65%
CYP inhibitory promiscuity	+	0.6837	68.37%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4429	44.29%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.8733	87.33%
Skin irritation	-	0.6631	66.31%
Skin corrosion	-	0.9402	94.02%
Ames mutagenesis	+	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6245	62.45%
Micronuclear	+	0.9200	92.00%
Hepatotoxicity	-	0.6750	67.50%
skin sensitisation	-	0.8541	85.41%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.8366	83.66%
Acute Oral Toxicity (c)	III	0.4845	48.45%
Estrogen receptor binding	+	0.6746	67.46%
Androgen receptor binding	+	0.6820	68.20%
Thyroid receptor binding	+	0.5978	59.78%
Glucocorticoid receptor binding	+	0.6479	64.79%
Aromatase binding	+	0.5631	56.31%
PPAR gamma	+	0.7665	76.65%
Honey bee toxicity	-	0.7772	77.72%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6950	69.50%
Fish aquatic toxicity	+	0.9606	96.06%

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	99.35%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.64%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.45%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	95.98%	99.15%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	95.21%	95.64%
CHEMBL3401	O75469	Pregnane X receptor	93.99%	94.73%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.86%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.83%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.56%	94.45%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	92.49%	90.71%
CHEMBL1951	P21397	Monoamine oxidase A	91.27%	91.49%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.61%	95.89%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.12%	96.09%
CHEMBL242	Q92731	Estrogen receptor beta	86.24%	98.35%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.74%	86.33%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	85.52%	95.78%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.46%	95.56%
CHEMBL3194	P02766	Transthyretin	83.64%	90.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.28%	99.23%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.43%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.50%	97.09%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	81.34%	85.11%
CHEMBL4208	P20618	Proteasome component C5	81.12%	90.00%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	80.94%	93.65%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.77%	95.89%

Plants that contains it

• Macroptilium atropurpureum

Cross-Links

• PubChem: 162902780
• LOTUS: LTS0114605
• wikiData: Q105211786