[(2R,3S,4S,5R,6S)-6-[3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-7-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate

Details

• Internal ID: 4c03d9ca-552a-452a-9b96-5dc862f44fc0
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: [(2R,3S,4S,5R,6S)-6-[3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-7-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
• SMILES (Canonical): COC1=C(C=CC(=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)OC4C(C(C(C(O4)COC(=O)C=CC5=CC=C(C=C5)O)O)O)O)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)COC(=O)/C=C/C5=CC=C(C=C5)O)O)O)O)O)O)O
• InChI: InChI=1S/C31H28O14/c1-41-20-10-15(5-8-18(20)33)30-28(39)26(37)24-19(34)11-17(12-21(24)44-30)43-31-29(40)27(38)25(36)22(45-31)13-42-23(35)9-4-14-2-6-16(32)7-3-14/h2-12,22,25,27,29,31-34,36,38-40H,13H2,1H3/b9-4+/t22-,25-,27+,29-,31-/m1/s1
• InChI Key: FSHKRIFUEGZCIN-DPFCLURTSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₂₈O₁₄
• Molecular Weight: 624.50 g/mol
• Exact Mass: 624.14790556 g/mol
• Topological Polar Surface Area (TPSA): 222.00 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 1.73
• H-Bond Acceptor: 14
• H-Bond Donor: 7
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5720	57.20%
Caco-2	-	0.8995	89.95%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.5995	59.95%
OATP2B1 inhibitior	-	0.5667	56.67%
OATP1B1 inhibitior	+	0.8753	87.53%
OATP1B3 inhibitior	+	0.9809	98.09%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.7274	72.74%
P-glycoprotein inhibitior	+	0.6577	65.77%
P-glycoprotein substrate	+	0.5261	52.61%
CYP3A4 substrate	+	0.6826	68.26%
CYP2C9 substrate	-	0.8149	81.49%
CYP2D6 substrate	-	0.8666	86.66%
CYP3A4 inhibition	-	0.8925	89.25%
CYP2C9 inhibition	-	0.8007	80.07%
CYP2C19 inhibition	-	0.8490	84.90%
CYP2D6 inhibition	-	0.9305	93.05%
CYP1A2 inhibition	-	0.9125	91.25%
CYP2C8 inhibition	+	0.9163	91.63%
CYP inhibitory promiscuity	-	0.7321	73.21%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6214	62.14%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9052	90.52%
Skin irritation	-	0.8169	81.69%
Skin corrosion	-	0.9464	94.64%
Ames mutagenesis	-	0.6128	61.28%
Human Ether-a-go-go-Related Gene inhibition	-	0.3803	38.03%
Micronuclear	+	0.7292	72.92%
Hepatotoxicity	-	0.8625	86.25%
skin sensitisation	-	0.9075	90.75%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.9651	96.51%
Acute Oral Toxicity (c)	III	0.5749	57.49%
Estrogen receptor binding	+	0.8032	80.32%
Androgen receptor binding	+	0.7293	72.93%
Thyroid receptor binding	+	0.5521	55.21%
Glucocorticoid receptor binding	+	0.6958	69.58%
Aromatase binding	+	0.5300	53.00%
PPAR gamma	+	0.6916	69.16%
Honey bee toxicity	-	0.7402	74.02%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9399	93.99%

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	99.52%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	98.26%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	98.25%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	96.96%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.43%	96.09%
CHEMBL3194	P02766	Transthyretin	95.28%	90.71%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	94.65%	95.64%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	93.99%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.38%	99.17%
CHEMBL2581	P07339	Cathepsin D	91.95%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.81%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.59%	95.56%
CHEMBL3438	Q05513	Protein kinase C zeta	90.51%	88.48%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.31%	94.45%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.91%	99.15%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.63%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	88.43%	94.73%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.42%	85.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.05%	95.89%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	86.95%	95.78%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	86.48%	90.71%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	85.33%	95.50%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.27%	86.92%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.67%	94.33%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	81.84%	89.62%
CHEMBL4208	P20618	Proteasome component C5	81.66%	90.00%

Plants that contains it

• Marrubium velutinum
• Rosa canina

Cross-Links

• PubChem: 10484053
• LOTUS: LTS0228918
• wikiData: Q105000633