[(2S,3R,4R,5S,6S)-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy-3,5-dihydroxy-6-methyloxan-4-yl] acetate

Details

• Internal ID: 83daa39d-7635-4ec4-9f0b-fc62ec8b2e21
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: [(2S,3R,4R,5S,6S)-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy-3,5-dihydroxy-6-methyloxan-4-yl] acetate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C=C4)O)O)O)OC(=O)C)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C=C4)O)O)O)OC(=O)C)O
• InChI: InChI=1S/C23H22O12/c1-8-17(29)21(33-9(2)24)19(31)23(32-8)35-22-18(30)16-14(28)6-11(25)7-15(16)34-20(22)10-3-4-12(26)13(27)5-10/h3-8,17,19,21,23,25-29,31H,1-2H3/t8-,17-,19+,21+,23-/m0/s1
• InChI Key: WIEJIBAASUWBGY-WSOJGYHASA-N
• Popularity: 2 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): 192.00 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 1.06
• H-Bond Acceptor: 12
• H-Bond Donor: 6
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7155	71.55%
Caco-2	-	0.8335	83.35%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7198	71.98%
OATP2B1 inhibitior	+	0.5853	58.53%
OATP1B1 inhibitior	+	0.9083	90.83%
OATP1B3 inhibitior	+	0.9360	93.60%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.6062	60.62%
P-glycoprotein inhibitior	+	0.5955	59.55%
P-glycoprotein substrate	-	0.5750	57.50%
CYP3A4 substrate	+	0.6612	66.12%
CYP2C9 substrate	+	0.5491	54.91%
CYP2D6 substrate	-	0.8773	87.73%
CYP3A4 inhibition	-	0.8092	80.92%
CYP2C9 inhibition	-	0.8456	84.56%
CYP2C19 inhibition	-	0.9033	90.33%
CYP2D6 inhibition	-	0.9601	96.01%
CYP1A2 inhibition	-	0.8248	82.48%
CYP2C8 inhibition	+	0.8597	85.97%
CYP inhibitory promiscuity	-	0.7646	76.46%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6520	65.20%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.8309	83.09%
Skin irritation	-	0.7203	72.03%
Skin corrosion	-	0.9297	92.97%
Ames mutagenesis	+	0.5963	59.63%
Human Ether-a-go-go-Related Gene inhibition	-	0.5390	53.90%
Micronuclear	+	0.9100	91.00%
Hepatotoxicity	+	0.5500	55.00%
skin sensitisation	-	0.9162	91.62%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.8021	80.21%
Acute Oral Toxicity (c)	III	0.5136	51.36%
Estrogen receptor binding	+	0.7217	72.17%
Androgen receptor binding	+	0.7789	77.89%
Thyroid receptor binding	-	0.5075	50.75%
Glucocorticoid receptor binding	+	0.6976	69.76%
Aromatase binding	-	0.6305	63.05%
PPAR gamma	+	0.6491	64.91%
Honey bee toxicity	-	0.7678	76.78%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5050	50.50%
Fish aquatic toxicity	+	0.9691	96.91%

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%
CHEMBL1951	P21397	Monoamine oxidase A	99.18%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	98.49%	89.00%
CHEMBL2581	P07339	Cathepsin D	97.67%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.30%	86.33%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	93.73%	95.64%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.58%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	90.89%	94.73%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.65%	99.15%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.82%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.80%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.30%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.67%	94.45%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	86.25%	95.78%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	86.18%	94.42%
CHEMBL3194	P02766	Transthyretin	85.46%	90.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.32%	99.23%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.48%	85.14%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	82.47%	81.11%
CHEMBL4208	P20618	Proteasome component C5	81.41%	90.00%
CHEMBL340	P08684	Cytochrome P450 3A4	81.16%	91.19%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	81.04%	93.65%

Plants that contains it

• Chorizanthe diffusa

Cross-Links

• PubChem: 100956675
• LOTUS: LTS0034646
• wikiData: Q105306179