3-(1,3-Benzodioxol-5-yl)-5-hydroxy-7-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one

Details

• Internal ID: 17a478af-5770-4ee2-bc1e-2c9bcbd63be1
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflavonoid O-glycosides
• IUPAC Name: 3-(1,3-benzodioxol-5-yl)-5-hydroxy-7-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): C1OC2=C(O1)C=C(C=C2)C3=COC4=CC(=CC(=C4C3=O)O)OC5C(C(C(C(O5)CO)O)O)O
• SMILES (Isomeric): C1OC2=C(O1)C=C(C=C2)C3=COC4=CC(=CC(=C4C3=O)O)OC5C(C(C(C(O5)CO)O)O)O
• InChI: InChI=1S/C22H20O11/c23-6-16-19(26)20(27)21(28)22(33-16)32-10-4-12(24)17-15(5-10)29-7-11(18(17)25)9-1-2-13-14(3-9)31-8-30-13/h1-5,7,16,19-24,26-28H,6,8H2
• InChI Key: MWQQQDCTBFECSA-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₀O₁₁
• Molecular Weight: 460.40 g/mol
• Exact Mass: 460.10056145 g/mol
• Topological Polar Surface Area (TPSA): 164.00 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 0.07
• H-Bond Acceptor: 11
• 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	+	0.5949	59.49%
Caco-2	-	0.9181	91.81%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.6301	63.01%
OATP2B1 inhibitior	-	0.5480	54.80%
OATP1B1 inhibitior	+	0.9437	94.37%
OATP1B3 inhibitior	+	0.9468	94.68%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.4758	47.58%
P-glycoprotein inhibitior	-	0.6786	67.86%
P-glycoprotein substrate	-	0.8663	86.63%
CYP3A4 substrate	+	0.6230	62.30%
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	+	0.5244	52.44%
CYP inhibitory promiscuity	+	0.5366	53.66%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5924	59.24%
Eye corrosion	-	0.9918	99.18%
Eye irritation	-	0.8495	84.95%
Skin irritation	-	0.8047	80.47%
Skin corrosion	-	0.9534	95.34%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4908	49.08%
Micronuclear	+	0.6933	69.33%
Hepatotoxicity	-	0.6446	64.46%
skin sensitisation	-	0.8767	87.67%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	+	0.5125	51.25%
Acute Oral Toxicity (c)	III	0.5647	56.47%
Estrogen receptor binding	+	0.7515	75.15%
Androgen receptor binding	+	0.6430	64.30%
Thyroid receptor binding	+	0.5340	53.40%
Glucocorticoid receptor binding	+	0.6057	60.57%
Aromatase binding	+	0.5838	58.38%
PPAR gamma	+	0.8406	84.06%
Honey bee toxicity	-	0.7127	71.27%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
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	99.50%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.25%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.12%	89.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	95.67%	96.77%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.21%	97.09%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	93.40%	94.80%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	93.18%	95.78%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.88%	94.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.52%	99.15%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.83%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.36%	86.33%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	88.79%	96.21%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.04%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.37%	96.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.11%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.49%	99.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.20%	85.14%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.69%	92.62%
CHEMBL3438	Q05513	Protein kinase C zeta	83.32%	88.48%
CHEMBL3922	P50579	Methionine aminopeptidase 2	82.66%	97.28%
CHEMBL4208	P20618	Proteasome component C5	82.40%	90.00%
CHEMBL4296	Q15858	Sodium channel protein type IX alpha subunit	81.90%	96.11%
CHEMBL226	P30542	Adenosine A1 receptor	81.37%	95.93%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	80.68%	95.53%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.32%	90.71%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.20%	100.00%

Plants that contains it

• Lupinus luteus

Cross-Links

• PubChem: 13338932
• LOTUS: LTS0186493
• wikiData: Q105173736