7-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4S)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5-hydroxychromen-4-one

Details

• Internal ID: 7ae350ec-4f77-4414-92fd-39f817693f25
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 7-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4S)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5-hydroxychromen-4-one
• SMILES (Canonical): C1C(C(C(O1)OC2C(C(C(OC2OC3=CC(=C4C(=C3)OC(=CC4=O)C5=CC(=C(C=C5)O)O)O)CO)O)O)O)(CO)O
• SMILES (Isomeric): C1[C@]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2OC3=CC(=C4C(=C3)OC(=CC4=O)C5=CC(=C(C=C5)O)O)O)CO)O)O)O)(CO)O
• InChI: InChI=1S/C26H28O15/c27-7-18-20(33)21(34)22(41-25-23(35)26(36,8-28)9-37-25)24(40-18)38-11-4-14(31)19-15(32)6-16(39-17(19)5-11)10-1-2-12(29)13(30)3-10/h1-6,18,20-25,27-31,33-36H,7-9H2/t18-,20-,21+,22-,23+,24-,25+,26+/m1/s1
• InChI Key: YSXNEFJASLJGTK-PCOFZURQSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₂₈O₁₅
• Molecular Weight: 580.50 g/mol
• Exact Mass: 580.14282018 g/mol
• Topological Polar Surface Area (TPSA): 245.00 Ų
• XlogP: -0.70
• Atomic LogP (AlogP): -1.78
• H-Bond Acceptor: 15
• H-Bond Donor: 9
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6445	64.45%
Caco-2	-	0.9158	91.58%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.6268	62.68%
OATP2B1 inhibitior	-	0.5602	56.02%
OATP1B1 inhibitior	+	0.9458	94.58%
OATP1B3 inhibitior	+	0.9377	93.77%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.6904	69.04%
P-glycoprotein inhibitior	-	0.5593	55.93%
P-glycoprotein substrate	-	0.5785	57.85%
CYP3A4 substrate	+	0.6671	66.71%
CYP2C9 substrate	-	0.8263	82.63%
CYP2D6 substrate	-	0.8608	86.08%
CYP3A4 inhibition	-	0.8434	84.34%
CYP2C9 inhibition	-	0.9185	91.85%
CYP2C19 inhibition	-	0.8482	84.82%
CYP2D6 inhibition	-	0.8986	89.86%
CYP1A2 inhibition	-	0.9073	90.73%
CYP2C8 inhibition	+	0.7086	70.86%
CYP inhibitory promiscuity	-	0.8029	80.29%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5523	55.23%
Eye corrosion	-	0.9926	99.26%
Eye irritation	-	0.9037	90.37%
Skin irritation	-	0.8084	80.84%
Skin corrosion	-	0.9520	95.20%
Ames mutagenesis	+	0.6036	60.36%
Human Ether-a-go-go-Related Gene inhibition	-	0.4004	40.04%
Micronuclear	+	0.6733	67.33%
Hepatotoxicity	-	0.7625	76.25%
skin sensitisation	-	0.8757	87.57%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.8054	80.54%
Acute Oral Toxicity (c)	III	0.5556	55.56%
Estrogen receptor binding	+	0.8360	83.60%
Androgen receptor binding	+	0.6783	67.83%
Thyroid receptor binding	+	0.5801	58.01%
Glucocorticoid receptor binding	+	0.5841	58.41%
Aromatase binding	+	0.7574	75.74%
PPAR gamma	+	0.8122	81.22%
Honey bee toxicity	-	0.6163	61.63%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6050	60.50%
Fish aquatic toxicity	+	0.7847	78.47%

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	99.85%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.17%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.97%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.10%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.78%	97.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	95.33%	99.15%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.68%	94.45%
CHEMBL226	P30542	Adenosine A1 receptor	94.51%	95.93%
CHEMBL2581	P07339	Cathepsin D	93.55%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.50%	95.56%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	92.17%	86.92%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.22%	95.89%
CHEMBL3922	P50579	Methionine aminopeptidase 2	88.05%	97.28%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.79%	86.33%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	85.73%	83.57%
CHEMBL6175	Q9H3R0	Lysine-specific demethylase 4C	85.68%	96.69%
CHEMBL3714130	P46095	G-protein coupled receptor 6	85.23%	97.36%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	85.04%	80.33%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	84.85%	95.83%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.28%	99.23%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.00%	90.71%
CHEMBL3194	P02766	Transthyretin	83.04%	90.71%
CHEMBL3401	O75469	Pregnane X receptor	82.43%	94.73%
CHEMBL4530	P00488	Coagulation factor XIII	81.68%	96.00%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	81.20%	92.88%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	81.03%	95.78%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	80.88%	95.71%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.08%	92.94%

Plants that contains it

• Capsicum annuum

Cross-Links

• PubChem: 14281860
• LOTUS: LTS0172920
• wikiData: Q105361151