3-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-oxo-4H-chromen-7-yl hexopyranoside

Details

• Internal ID: 3be9cbfa-9fcb-4ae9-b5cd-e39dbffd38c5
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflavonoid O-glycosides
• IUPAC Name: 3-(2,3-dihydro-1,4-benzodioxin-6-yl)-7-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• InChI: InChI=1S/C23H22O10/c24-9-18-20(26)21(27)22(28)23(33-18)32-12-2-3-13-16(8-12)31-10-14(19(13)25)11-1-4-15-17(7-11)30-6-5-29-15/h1-4,7-8,10,18,20-24,26-28H,5-6,9H2
• InChI Key: BAIAFWNWTHLWBX-UHFFFAOYSA-N
• Popularity: 7 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₂O₁₀
• Molecular Weight: 458.40 g/mol
• Exact Mass: 458.12129689 g/mol
• Topological Polar Surface Area (TPSA): 144.00 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 0.41
• H-Bond Acceptor: 10
• H-Bond Donor: 4
• Rotatable Bonds: 4

Synonyms

• SMR000339619
• 3-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-oxo-4H-chromen-7-yl hexopyranoside
• Opera_ID_96
• ChemDiv1_000894
• Oprea1_700130
• CBDivE_005345
• MLS003878267
• CHEMBL1609792
• BDBM95965
• cid_3811495
• HMS589I14
• HMS2757O03
• MFCD00306303
• AKOS001613526
• AKOS016370842
• 3-(2,3-dihydro-1,4-benzodioxin-6-yl)-7-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• SR-01000404436
• SR-01000404436-1
• 3-(2,3-dihydro-1,4-benzodioxin-6-yl)-7-(3,4,5-trihydroxy-6-methylol-tetrahydropyran-2-yl)oxy-chromone
• 3-(2,3-dihydro-1,4-benzodioxin-6-yl)-7-[[3,4,5-trihydroxy-6-(hydroxymethyl)-2-oxanyl]oxy]-1-benzopyran-4-one
• 3-(2,3-dihydro-1,4-benzodioxin-6-yl)-7-[6-(hydroxymethyl)-3,4,5-tris(oxidanyl)oxan-2-yl]oxy-chromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6163	61.63%
Caco-2	-	0.9077	90.77%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.6911	69.11%
OATP2B1 inhibitior	-	0.5582	55.82%
OATP1B1 inhibitior	+	0.9401	94.01%
OATP1B3 inhibitior	+	0.9375	93.75%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8037	80.37%
BSEP inhibitior	+	0.6771	67.71%
P-glycoprotein inhibitior	-	0.5266	52.66%
P-glycoprotein substrate	-	0.8779	87.79%
CYP3A4 substrate	+	0.6403	64.03%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8291	82.91%
CYP3A4 inhibition	-	0.9442	94.42%
CYP2C9 inhibition	-	0.7979	79.79%
CYP2C19 inhibition	-	0.8496	84.96%
CYP2D6 inhibition	-	0.9248	92.48%
CYP1A2 inhibition	-	0.8285	82.85%
CYP2C8 inhibition	+	0.4589	45.89%
CYP inhibitory promiscuity	-	0.7899	78.99%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6759	67.59%
Eye corrosion	-	0.9916	99.16%
Eye irritation	-	0.8964	89.64%
Skin irritation	-	0.8255	82.55%
Skin corrosion	-	0.9647	96.47%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4718	47.18%
Micronuclear	-	0.5167	51.67%
Hepatotoxicity	-	0.6250	62.50%
skin sensitisation	-	0.9043	90.43%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.6861	68.61%
Acute Oral Toxicity (c)	III	0.4836	48.36%
Estrogen receptor binding	+	0.7388	73.88%
Androgen receptor binding	+	0.7829	78.29%
Thyroid receptor binding	-	0.5214	52.14%
Glucocorticoid receptor binding	+	0.5766	57.66%
Aromatase binding	-	0.4840	48.40%
PPAR gamma	+	0.7973	79.73%
Honey bee toxicity	-	0.7384	73.84%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6050	60.50%
Fish aquatic toxicity	+	0.6987	69.87%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293277	O15118	Niemann-Pick C1 protein	562.3 nM	Potency	via Super-PRED
CHEMBL1293294	P51151	Ras-related protein Rab-9A	501.2 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.25%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.27%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.75%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.57%	97.09%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	92.04%	95.78%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.74%	94.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	91.34%	94.80%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.13%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.04%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.50%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.83%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.82%	95.89%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.62%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.61%	96.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.32%	92.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.22%	99.17%
CHEMBL226	P30542	Adenosine A1 receptor	83.48%	95.93%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.14%	99.15%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	82.05%	95.53%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	81.35%	96.77%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.23%	95.83%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.13%	100.00%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	80.66%	80.33%
CHEMBL3438	Q05513	Protein kinase C zeta	80.62%	88.48%

Plants that contains it

• Panax quinquefolius

Cross-Links

• PubChem: 3811495
• LOTUS: LTS0040035
• wikiData: Q104922182