[(2S,3R,4S,5R,6R)-4-[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl] acetate

Details

• Internal ID: 0dffc9d3-9aa3-43f9-82b9-2be25c4d759c
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 3-O-methylated flavonoids
• IUPAC Name: [(2S,3R,4S,5R,6R)-4-[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl] acetate
• SMILES (Canonical): CC(=O)OC1C(C(C(C(O1)CO)O)OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C=C4)O)OC)O
• SMILES (Isomeric): CC(=O)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C=C4)O)OC)O
• InChI: InChI=1S/C24H24O13/c1-9(26)34-24-20(32)22(18(30)16(8-25)36-24)37-23-19(31)17-13(29)6-11(27)7-15(17)35-21(23)10-3-4-12(28)14(5-10)33-2/h3-7,16,18,20,22,24-25,27-30,32H,8H2,1-2H3/t16-,18-,20-,22+,24-/m1/s1
• InChI Key: TZCCUAFGXBAIAM-YEEBRUQLSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₂₄O₁₃
• Molecular Weight: 520.40 g/mol
• Exact Mass: 520.12169082 g/mol
• Topological Polar Surface Area (TPSA): 202.00 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 0.33
• H-Bond Acceptor: 13
• H-Bond Donor: 6
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7677	76.77%
Caco-2	-	0.8933	89.33%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.5993	59.93%
OATP2B1 inhibitior	-	0.5585	55.85%
OATP1B1 inhibitior	+	0.8772	87.72%
OATP1B3 inhibitior	+	0.8648	86.48%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.5664	56.64%
P-glycoprotein inhibitior	+	0.6032	60.32%
P-glycoprotein substrate	-	0.5556	55.56%
CYP3A4 substrate	+	0.6639	66.39%
CYP2C9 substrate	-	0.6131	61.31%
CYP2D6 substrate	-	0.8620	86.20%
CYP3A4 inhibition	-	0.8555	85.55%
CYP2C9 inhibition	-	0.7287	72.87%
CYP2C19 inhibition	-	0.9018	90.18%
CYP2D6 inhibition	-	0.9595	95.95%
CYP1A2 inhibition	-	0.9391	93.91%
CYP2C8 inhibition	+	0.8332	83.32%
CYP inhibitory promiscuity	-	0.7102	71.02%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7367	73.67%
Eye corrosion	-	0.9876	98.76%
Eye irritation	-	0.8895	88.95%
Skin irritation	-	0.8467	84.67%
Skin corrosion	-	0.9593	95.93%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5411	54.11%
Micronuclear	+	0.7033	70.33%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.9232	92.32%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.8074	80.74%
Acute Oral Toxicity (c)	III	0.6529	65.29%
Estrogen receptor binding	+	0.7764	77.64%
Androgen receptor binding	+	0.7170	71.70%
Thyroid receptor binding	-	0.5812	58.12%
Glucocorticoid receptor binding	+	0.7445	74.45%
Aromatase binding	-	0.5392	53.92%
PPAR gamma	+	0.6433	64.33%
Honey bee toxicity	-	0.7533	75.33%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6549	65.49%
Fish aquatic toxicity	+	0.7746	77.46%

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	99.53%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.36%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.63%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.40%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.73%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.42%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.39%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.21%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.46%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.27%	95.56%
CHEMBL3194	P02766	Transthyretin	86.25%	90.71%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	85.84%	95.64%
CHEMBL3401	O75469	Pregnane X receptor	85.68%	94.73%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.05%	92.62%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.92%	99.15%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	83.49%	95.78%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.52%	96.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.30%	86.92%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.89%	94.33%
CHEMBL340	P08684	Cytochrome P450 3A4	80.59%	91.19%

Plants that contains it

• Senecio mairetianus

Cross-Links

• PubChem: 163056082
• LOTUS: LTS0026986
• wikiData: Q105267968