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

Details

• Internal ID: 3c88be98-a20b-45d6-b3c5-778d1b5d3829
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 3-hydroxy-2-(7-methoxy-1,3-benzodioxol-5-yl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): COC1=CC(=CC2=C1OCO2)C3=C(C(=O)C4=C(O3)C=C(C=C4)OC5C(C(C(C(O5)CO)O)O)O)O
• SMILES (Isomeric): COC1=CC(=CC2=C1OCO2)C3=C(C(=O)C4=C(O3)C=C(C=C4)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O
• InChI: InChI=1S/C23H22O12/c1-30-13-4-9(5-14-22(13)32-8-31-14)21-19(28)16(25)11-3-2-10(6-12(11)34-21)33-23-20(29)18(27)17(26)15(7-24)35-23/h2-6,15,17-18,20,23-24,26-29H,7-8H2,1H3/t15-,17-,18+,20-,23-/m1/s1
• InChI Key: FHBQRFOFZLGUSR-WCTCFVGCSA-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: 0.70
• 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	-	0.8968	89.68%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6374	63.74%
OATP2B1 inhibitior	-	0.7006	70.06%
OATP1B1 inhibitior	+	0.9326	93.26%
OATP1B3 inhibitior	+	0.9728	97.28%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.7432	74.32%
P-glycoprotein inhibitior	-	0.4448	44.48%
P-glycoprotein substrate	-	0.5376	53.76%
CYP3A4 substrate	+	0.6569	65.69%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8324	83.24%
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	+	0.5837	58.37%
CYP inhibitory promiscuity	+	0.6208	62.08%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5596	55.96%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.9048	90.48%
Skin irritation	-	0.8137	81.37%
Skin corrosion	-	0.9475	94.75%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3693	36.93%
Micronuclear	+	0.7033	70.33%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.8847	88.47%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.7788	77.88%
Acute Oral Toxicity (c)	III	0.7562	75.62%
Estrogen receptor binding	+	0.8154	81.54%
Androgen receptor binding	+	0.5836	58.36%
Thyroid receptor binding	+	0.5176	51.76%
Glucocorticoid receptor binding	+	0.6659	66.59%
Aromatase binding	+	0.5545	55.45%
PPAR gamma	+	0.7532	75.32%
Honey bee toxicity	-	0.6894	68.94%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6049	60.49%
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
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.79%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.23%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.90%	94.00%
CHEMBL2581	P07339	Cathepsin D	95.40%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.87%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.78%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.62%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.24%	96.09%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	92.73%	92.62%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	92.57%	96.77%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	90.95%	96.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.64%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.07%	86.33%
CHEMBL3714130	P46095	G-protein coupled receptor 6	88.78%	97.36%
CHEMBL220	P22303	Acetylcholinesterase	88.41%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.39%	99.17%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	84.41%	96.21%
CHEMBL3401	O75469	Pregnane X receptor	84.06%	94.73%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	83.13%	92.38%
CHEMBL3438	Q05513	Protein kinase C zeta	82.44%	88.48%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.40%	99.15%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.86%	99.23%
CHEMBL4208	P20618	Proteasome component C5	81.28%	90.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.18%	90.71%
CHEMBL1951	P21397	Monoamine oxidase A	80.27%	91.49%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.19%	100.00%

Plants that contains it

• Calendula officinalis
• Cydonia oblonga

Cross-Links

• PubChem: 10767373
• LOTUS: LTS0168909
• wikiData: Q105188699