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

Details

• Internal ID: 9533dd25-cb20-415c-bf13-9b20817760fd
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflavonoid O-glycosides
• IUPAC Name: 9-methoxy-7-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-[1,3]dioxolo[4,5-g]chromen-8-one
• SMILES (Canonical): COC1=C2C(=CC3=C1OCO3)OC=C(C2=O)C4=CC=C(C=C4)OC5C(C(C(C(O5)CO)O)O)O
• SMILES (Isomeric): COC1=C2C(=CC3=C1OCO3)OC=C(C2=O)C4=CC=C(C=C4)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O
• InChI: InChI=1S/C23H22O11/c1-29-22-16-13(6-14-21(22)32-9-31-14)30-8-12(17(16)25)10-2-4-11(5-3-10)33-23-20(28)19(27)18(26)15(7-24)34-23/h2-6,8,15,18-20,23-24,26-28H,7,9H2,1H3/t15-,18-,19+,20-,23-/m1/s1
• InChI Key: MLRDPISQDDYRHC-BSTKLLGTSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₂O₁₁
• Molecular Weight: 474.40 g/mol
• Exact Mass: 474.11621151 g/mol
• Topological Polar Surface Area (TPSA): 153.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 0.38
• H-Bond Acceptor: 11
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6191	61.91%
Caco-2	-	0.8418	84.18%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.6374	63.74%
OATP2B1 inhibitior	-	0.8484	84.84%
OATP1B1 inhibitior	+	0.9453	94.53%
OATP1B3 inhibitior	+	0.9728	97.28%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.6517	65.17%
P-glycoprotein inhibitior	+	0.6191	61.91%
P-glycoprotein substrate	-	0.8297	82.97%
CYP3A4 substrate	+	0.6283	62.83%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8291	82.91%
CYP3A4 inhibition	-	0.5836	58.36%
CYP2C9 inhibition	-	0.7784	77.84%
CYP2C19 inhibition	-	0.7015	70.15%
CYP2D6 inhibition	-	0.8616	86.16%
CYP1A2 inhibition	-	0.9048	90.48%
CYP2C8 inhibition	+	0.4602	46.02%
CYP inhibitory promiscuity	+	0.6208	62.08%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5596	55.96%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.8998	89.98%
Skin irritation	-	0.8137	81.37%
Skin corrosion	-	0.9475	94.75%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6837	68.37%
Micronuclear	+	0.7033	70.33%
Hepatotoxicity	-	0.6125	61.25%
skin sensitisation	-	0.8847	88.47%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.7886	78.86%
Acute Oral Toxicity (c)	III	0.7562	75.62%
Estrogen receptor binding	+	0.8269	82.69%
Androgen receptor binding	+	0.7146	71.46%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.6690	66.90%
Aromatase binding	+	0.5345	53.45%
PPAR gamma	+	0.7681	76.81%
Honey bee toxicity	-	0.7535	75.35%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.7290	72.90%

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	99.29%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.09%	98.95%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	97.05%	96.77%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.64%	94.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.53%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	93.90%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.41%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.64%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.49%	86.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	90.52%	92.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.11%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.93%	96.00%
CHEMBL4208	P20618	Proteasome component C5	87.52%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.48%	94.45%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.40%	95.83%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.20%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.05%	95.89%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.03%	85.14%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	81.51%	94.80%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	81.31%	82.67%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	81.18%	95.53%
CHEMBL1907	P15144	Aminopeptidase N	80.95%	93.31%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.27%	99.15%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	80.19%	96.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.11%	86.92%

Plants that contains it

• Iris pseudopumila

Cross-Links

• PubChem: 10961746
• LOTUS: LTS0181954
• wikiData: Q104888991