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

Details

• Internal ID: e19ae098-f018-4b76-aca4-7ce1adaf808e
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: [(2S,3R,4S,5S,6R)-2-[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] acetate
• SMILES (Canonical): CC(=O)OC1C(C(C(OC1OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C=C4)O)OC)CO)O)O
• SMILES (Isomeric): CC(=O)O[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C=C4)O)OC)CO)O)O
• InChI: InChI=1S/C24H24O13/c1-9(26)34-23-20(32)18(30)16(8-25)36-24(23)37-22-19(31)17-13(29)6-11(27)7-15(17)35-21(22)10-3-4-12(28)14(5-10)33-2/h3-7,16,18,20,23-25,27-30,32H,8H2,1-2H3/t16-,18-,20+,23-,24+/m1/s1
• InChI Key: ORAIMDQSZIUQPL-PIEFEKBNSA-N
• Popularity: 2 references 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	-	0.6066	60.66%
Caco-2	-	0.8867	88.67%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.5789	57.89%
OATP2B1 inhibitior	-	0.5603	56.03%
OATP1B1 inhibitior	+	0.8755	87.55%
OATP1B3 inhibitior	+	0.9761	97.61%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.6269	62.69%
P-glycoprotein inhibitior	+	0.5775	57.75%
P-glycoprotein substrate	-	0.5767	57.67%
CYP3A4 substrate	+	0.6604	66.04%
CYP2C9 substrate	-	0.8246	82.46%
CYP2D6 substrate	-	0.8713	87.13%
CYP3A4 inhibition	-	0.8925	89.25%
CYP2C9 inhibition	-	0.9040	90.40%
CYP2C19 inhibition	-	0.9391	93.91%
CYP2D6 inhibition	-	0.9601	96.01%
CYP1A2 inhibition	-	0.9300	93.00%
CYP2C8 inhibition	+	0.8312	83.12%
CYP inhibitory promiscuity	-	0.8415	84.15%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7305	73.05%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.8949	89.49%
Skin irritation	-	0.8464	84.64%
Skin corrosion	-	0.9565	95.65%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4145	41.45%
Micronuclear	+	0.6733	67.33%
Hepatotoxicity	-	0.6000	60.00%
skin sensitisation	-	0.9405	94.05%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.8627	86.27%
Acute Oral Toxicity (c)	III	0.6381	63.81%
Estrogen receptor binding	+	0.8362	83.62%
Androgen receptor binding	+	0.7084	70.84%
Thyroid receptor binding	-	0.5449	54.49%
Glucocorticoid receptor binding	+	0.7618	76.18%
Aromatase binding	-	0.5135	51.35%
PPAR gamma	+	0.6513	65.13%
Honey bee toxicity	-	0.7596	75.96%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6549	65.49%
Fish aquatic toxicity	+	0.8147	81.47%

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	99.17%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.12%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.00%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.16%	94.00%
CHEMBL2581	P07339	Cathepsin D	96.07%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.88%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.13%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.90%	86.33%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	92.05%	95.64%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.63%	95.56%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.74%	86.92%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.32%	99.15%
CHEMBL3401	O75469	Pregnane X receptor	87.12%	94.73%
CHEMBL3194	P02766	Transthyretin	86.71%	90.71%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.35%	85.14%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	84.48%	95.78%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.94%	96.00%
CHEMBL4208	P20618	Proteasome component C5	82.63%	90.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.06%	94.33%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.34%	95.50%

Plants that contains it

• Sedum acre

Cross-Links

• PubChem: 14186854
• LOTUS: LTS0120333
• wikiData: Q105197355