(2S,3S,4S,5R,6S)-6-[[6-(2,3-dihydroxy-4-methoxyphenyl)-9-hydroxy-8-oxo-[1,3]dioxolo[4,5-g]chromen-7-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

Details

• Internal ID: 3e7e3dfb-9658-49ce-baf9-5f6081ab963d
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glucuronides > Flavonoid-3-O-glucuronides
• IUPAC Name: (2S,3S,4S,5R,6S)-6-[[6-(2,3-dihydroxy-4-methoxyphenyl)-9-hydroxy-8-oxo-[1,3]dioxolo[4,5-g]chromen-7-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• SMILES (Canonical): COC1=C(C(=C(C=C1)C2=C(C(=O)C3=C(C4=C(C=C3O2)OCO4)O)OC5C(C(C(C(O5)C(=O)O)O)O)O)O)O
• SMILES (Isomeric): COC1=C(C(=C(C=C1)C2=C(C(=O)C3=C(C4=C(C=C3O2)OCO4)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)C(=O)O)O)O)O)O)O
• InChI: InChI=1S/C23H20O15/c1-33-7-3-2-6(11(24)12(7)25)18-20(37-23-17(30)15(28)16(29)21(38-23)22(31)32)14(27)10-8(36-18)4-9-19(13(10)26)35-5-34-9/h2-4,15-17,21,23-26,28-30H,5H2,1H3,(H,31,32)/t15-,16-,17+,21-,23+/m0/s1
• InChI Key: DDUOYJGQMDFRBY-QJAHINBCSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₀O₁₅
• Molecular Weight: 536.40 g/mol
• Exact Mass: 536.08021993 g/mol
• Topological Polar Surface Area (TPSA): 231.00 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): -0.41
• H-Bond Acceptor: 14
• H-Bond Donor: 7
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7020	70.20%
Caco-2	-	0.8780	87.80%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7109	71.09%
OATP2B1 inhibitior	-	0.5510	55.10%
OATP1B1 inhibitior	+	0.9146	91.46%
OATP1B3 inhibitior	+	0.9716	97.16%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.6644	66.44%
P-glycoprotein inhibitior	-	0.5184	51.84%
P-glycoprotein substrate	-	0.6228	62.28%
CYP3A4 substrate	+	0.6533	65.33%
CYP2C9 substrate	-	0.8232	82.32%
CYP2D6 substrate	-	0.8719	87.19%
CYP3A4 inhibition	+	0.6858	68.58%
CYP2C9 inhibition	+	0.6205	62.05%
CYP2C19 inhibition	+	0.5172	51.72%
CYP2D6 inhibition	-	0.7460	74.60%
CYP1A2 inhibition	-	0.7399	73.99%
CYP2C8 inhibition	+	0.7793	77.93%
CYP inhibitory promiscuity	+	0.6490	64.90%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5299	52.99%
Eye corrosion	-	0.9880	98.80%
Eye irritation	-	0.8825	88.25%
Skin irritation	-	0.7653	76.53%
Skin corrosion	-	0.9319	93.19%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3893	38.93%
Micronuclear	+	0.8274	82.74%
Hepatotoxicity	-	0.6750	67.50%
skin sensitisation	-	0.8730	87.30%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.8937	89.37%
Acute Oral Toxicity (c)	III	0.6759	67.59%
Estrogen receptor binding	+	0.7957	79.57%
Androgen receptor binding	+	0.6687	66.87%
Thyroid receptor binding	-	0.5539	55.39%
Glucocorticoid receptor binding	+	0.6999	69.99%
Aromatase binding	-	0.4879	48.79%
PPAR gamma	+	0.5949	59.49%
Honey bee toxicity	-	0.7686	76.86%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.9347	93.47%

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	99.03%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	97.65%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.08%	89.00%
CHEMBL2581	P07339	Cathepsin D	96.05%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.26%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.10%	95.56%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	94.48%	96.77%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.00%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.38%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.07%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.83%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.78%	94.45%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.49%	92.62%
CHEMBL3194	P02766	Transthyretin	85.42%	90.71%
CHEMBL4208	P20618	Proteasome component C5	85.40%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.26%	95.89%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	84.99%	95.64%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.48%	96.00%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	84.28%	94.42%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.22%	100.00%
CHEMBL2535	P11166	Glucose transporter	83.57%	98.75%
CHEMBL3401	O75469	Pregnane X receptor	83.03%	94.73%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.59%	90.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.32%	99.23%
CHEMBL2413	P32246	C-C chemokine receptor type 1	81.43%	89.50%
CHEMBL3492	P49721	Proteasome Macropain subunit	80.30%	90.24%

Plants that contains it

• Spinacia oleracea

Cross-Links

• PubChem: 11016952
• LOTUS: LTS0114332
• wikiData: Q104976860