9-hydroxy-6-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-[1,3]dioxolo[4,5-g]chromen-8-one

Details

• Internal ID: 67c83cc6-be3a-489d-9dec-89f874097016
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 9-hydroxy-6-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-[1,3]dioxolo[4,5-g]chromen-8-one
• SMILES (Canonical): C1OC2=C(O1)C(=C3C(=C2)OC(=C(C3=O)OC4C(C(C(C(O4)CO)O)O)O)C5=CC=C(C=C5)O)O
• SMILES (Isomeric): C1OC2=C(O1)C(=C3C(=C2)OC(=C(C3=O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)C5=CC=C(C=C5)O)O
• InChI: InChI=1S/C22H20O12/c23-6-12-14(25)17(28)18(29)22(33-12)34-21-16(27)13-10(5-11-20(15(13)26)31-7-30-11)32-19(21)8-1-3-9(24)4-2-8/h1-5,12,14,17-18,22-26,28-29H,6-7H2/t12-,14-,17+,18-,22+/m1/s1
• InChI Key: PEBSHTGUNSXVEZ-OOVDEOTFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₀O₁₂
• Molecular Weight: 476.40 g/mol
• Exact Mass: 476.09547607 g/mol
• Topological Polar Surface Area (TPSA): 185.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): -0.22
• H-Bond Acceptor: 12
• 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	+	0.5949	59.49%
Caco-2	-	0.9115	91.15%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.6301	63.01%
OATP2B1 inhibitior	+	0.5833	58.33%
OATP1B1 inhibitior	+	0.9119	91.19%
OATP1B3 inhibitior	+	0.9468	94.68%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.5844	58.44%
P-glycoprotein inhibitior	-	0.5609	56.09%
P-glycoprotein substrate	-	0.7510	75.10%
CYP3A4 substrate	+	0.6153	61.53%
CYP2C9 substrate	-	0.6762	67.62%
CYP2D6 substrate	-	0.8575	85.75%
CYP3A4 inhibition	-	0.5780	57.80%
CYP2C9 inhibition	-	0.8821	88.21%
CYP2C19 inhibition	-	0.7756	77.56%
CYP2D6 inhibition	-	0.8441	84.41%
CYP1A2 inhibition	-	0.8878	88.78%
CYP2C8 inhibition	+	0.7552	75.52%
CYP inhibitory promiscuity	+	0.5366	53.66%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5924	59.24%
Eye corrosion	-	0.9918	99.18%
Eye irritation	-	0.7903	79.03%
Skin irritation	-	0.8047	80.47%
Skin corrosion	-	0.9534	95.34%
Ames mutagenesis	+	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4562	45.62%
Micronuclear	+	0.6933	69.33%
Hepatotoxicity	-	0.7071	70.71%
skin sensitisation	-	0.8767	87.67%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.8543	85.43%
Acute Oral Toxicity (c)	III	0.5647	56.47%
Estrogen receptor binding	+	0.7292	72.92%
Androgen receptor binding	+	0.7774	77.74%
Thyroid receptor binding	-	0.5352	53.52%
Glucocorticoid receptor binding	+	0.7149	71.49%
Aromatase binding	+	0.6438	64.38%
PPAR gamma	+	0.6737	67.37%
Honey bee toxicity	-	0.7038	70.38%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.8350	83.50%

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	99.61%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.19%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.56%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.77%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.93%	94.00%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	92.09%	95.64%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.89%	97.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	91.86%	96.77%
CHEMBL3401	O75469	Pregnane X receptor	89.99%	94.73%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.14%	85.14%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	88.66%	95.78%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.49%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.70%	96.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.62%	99.15%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.73%	100.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.60%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.01%	95.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.77%	95.89%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.09%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.57%	92.62%

Plants that contains it

• Persicaria tinctoria

Cross-Links

• PubChem: 14542804
• LOTUS: LTS0051531
• wikiData: Q105206888