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

Details

• Internal ID: 9b4c628b-58c8-4132-9f00-8142276bf5ab
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflavonoid O-glycosides
• IUPAC Name: 9-hydroxy-7-[3-methoxy-4-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-[1,3]dioxolo[4,5-g]chromen-8-one
• SMILES (Canonical): COC1=C(C=CC(=C1)C2=COC3=CC4=C(C(=C3C2=O)O)OCO4)OC5C(C(C(C(O5)CO)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)C2=COC3=CC4=C(C(=C3C2=O)O)OCO4)O[C@@H]5[C@H]([C@@H]([C@H]([C@@H](O5)CO)O)O)O
• InChI: InChI=1S/C23H22O12/c1-30-12-4-9(2-3-11(12)34-23-21(29)20(28)18(26)15(6-24)35-23)10-7-31-13-5-14-22(33-8-32-14)19(27)16(13)17(10)25/h2-5,7,15,18,20-21,23-24,26-29H,6,8H2,1H3/t15-,18-,20+,21-,23-/m0/s1
• InChI Key: ZYXMBDJAUWLBQW-WNZZMIDNSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₂O₁₂
• Molecular Weight: 490.40 g/mol
• Exact Mass: 490.11112613 g/mol
• Topological Polar Surface Area (TPSA): 174.00 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 0.08
• H-Bond Acceptor: 12
• H-Bond Donor: 5
• 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	-	0.8690	86.90%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.6374	63.74%
OATP2B1 inhibitior	-	0.8450	84.50%
OATP1B1 inhibitior	+	0.9220	92.20%
OATP1B3 inhibitior	+	0.9728	97.28%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8173	81.73%
P-glycoprotein inhibitior	-	0.4441	44.41%
P-glycoprotein substrate	-	0.6922	69.22%
CYP3A4 substrate	+	0.6478	64.78%
CYP2C9 substrate	-	0.8485	84.85%
CYP2D6 substrate	-	0.8501	85.01%
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	+	0.6566	65.66%
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	-	0.9143	91.43%
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	-	0.4099	40.99%
Micronuclear	+	0.7033	70.33%
Hepatotoxicity	-	0.6375	63.75%
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	-	0.8002	80.02%
Acute Oral Toxicity (c)	III	0.7562	75.62%
Estrogen receptor binding	+	0.8250	82.50%
Androgen receptor binding	+	0.5661	56.61%
Thyroid receptor binding	-	0.5054	50.54%
Glucocorticoid receptor binding	+	0.6880	68.80%
Aromatase binding	-	0.4849	48.49%
PPAR gamma	+	0.8016	80.16%
Honey bee toxicity	-	0.6818	68.18%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6449	64.49%
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
CHEMBL2581	P07339	Cathepsin D	98.77%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.00%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.11%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.96%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.91%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	95.06%	96.77%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.33%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.11%	85.14%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	92.17%	96.21%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.58%	95.56%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	88.55%	92.62%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.06%	96.00%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	87.62%	82.67%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	87.34%	95.53%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.26%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.85%	97.09%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	86.66%	95.78%
CHEMBL3438	Q05513	Protein kinase C zeta	85.17%	88.48%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	84.68%	92.38%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.21%	99.17%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.66%	100.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.89%	90.71%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.62%	97.36%
CHEMBL4208	P20618	Proteasome component C5	80.69%	90.00%

Plants that contains it

• Iris florentina

Cross-Links

• PubChem: 162910270
• LOTUS: LTS0051033
• wikiData: Q105386509