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

Details

• Internal ID: c273e426-964d-41ec-b925-8f996763e55c
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 7-[(2S,3R,4R,5S,6R)-5-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chromen-4-one
• SMILES (Canonical): C1C(C(C(O1)OC2C(OC(C(C2O)O)OC3=CC(=C4C(=C3)OC(=CC4=O)C5=CC=C(C=C5)O)O)CO)O)(CO)O
• SMILES (Isomeric): C1[C@@]([C@H]([C@@H](O1)O[C@@H]2[C@H](O[C@H]([C@@H]([C@H]2O)O)OC3=CC(=C4C(=C3)OC(=CC4=O)C5=CC=C(C=C5)O)O)CO)O)(CO)O
• InChI: InChI=1S/C26H28O14/c27-8-18-22(40-25-23(34)26(35,9-28)10-36-25)20(32)21(33)24(39-18)37-13-5-14(30)19-15(31)7-16(38-17(19)6-13)11-1-3-12(29)4-2-11/h1-7,18,20-25,27-30,32-35H,8-10H2/t18-,20-,21-,22-,23+,24-,25+,26-/m1/s1
• InChI Key: FDRBRRBUPLHXEM-RXVKCJIPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₂₈O₁₄
• Molecular Weight: 564.50 g/mol
• Exact Mass: 564.14790556 g/mol
• Topological Polar Surface Area (TPSA): 225.00 Ų
• XlogP: -0.90
• Atomic LogP (AlogP): -1.49
• H-Bond Acceptor: 14
• H-Bond Donor: 8
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5874	58.74%
Caco-2	-	0.9213	92.13%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.6429	64.29%
OATP2B1 inhibitior	-	0.5595	55.95%
OATP1B1 inhibitior	+	0.9424	94.24%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9039	90.39%
P-glycoprotein inhibitior	-	0.5733	57.33%
P-glycoprotein substrate	-	0.6103	61.03%
CYP3A4 substrate	+	0.6679	66.79%
CYP2C9 substrate	-	0.8271	82.71%
CYP2D6 substrate	-	0.8606	86.06%
CYP3A4 inhibition	-	0.8440	84.40%
CYP2C9 inhibition	-	0.9319	93.19%
CYP2C19 inhibition	-	0.8680	86.80%
CYP2D6 inhibition	-	0.9030	90.30%
CYP1A2 inhibition	-	0.9212	92.12%
CYP2C8 inhibition	+	0.6970	69.70%
CYP inhibitory promiscuity	-	0.8119	81.19%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5235	52.35%
Eye corrosion	-	0.9925	99.25%
Eye irritation	-	0.9146	91.46%
Skin irritation	-	0.8079	80.79%
Skin corrosion	-	0.9542	95.42%
Ames mutagenesis	+	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6450	64.50%
Micronuclear	+	0.6233	62.33%
Hepatotoxicity	-	0.8250	82.50%
skin sensitisation	-	0.8881	88.81%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.7634	76.34%
Acute Oral Toxicity (c)	III	0.5720	57.20%
Estrogen receptor binding	+	0.7735	77.35%
Androgen receptor binding	+	0.7234	72.34%
Thyroid receptor binding	-	0.5288	52.88%
Glucocorticoid receptor binding	-	0.5081	50.81%
Aromatase binding	+	0.6903	69.03%
PPAR gamma	+	0.7807	78.07%
Honey bee toxicity	-	0.6092	60.92%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5950	59.50%
Fish aquatic toxicity	+	0.7344	73.44%

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	99.69%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.48%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.16%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.20%	97.09%
CHEMBL2581	P07339	Cathepsin D	93.99%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.21%	94.45%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	92.96%	86.92%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.30%	95.56%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	92.01%	83.57%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.60%	99.15%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.92%	95.89%
CHEMBL242	Q92731	Estrogen receptor beta	90.46%	98.35%
CHEMBL6175	Q9H3R0	Lysine-specific demethylase 4C	89.95%	96.69%
CHEMBL226	P30542	Adenosine A1 receptor	89.60%	95.93%
CHEMBL3922	P50579	Methionine aminopeptidase 2	87.37%	97.28%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.65%	86.33%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.63%	95.83%
CHEMBL4530	P00488	Coagulation factor XIII	84.77%	96.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.80%	90.71%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	83.26%	80.33%
CHEMBL1951	P21397	Monoamine oxidase A	83.19%	91.49%
CHEMBL3194	P02766	Transthyretin	82.61%	90.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.50%	99.23%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	82.19%	95.78%
CHEMBL3401	O75469	Pregnane X receptor	81.91%	94.73%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.06%	95.89%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	80.92%	95.71%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	80.87%	95.53%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	80.54%	91.71%

Plants that contains it

• Apium graveolens
• Calendula officinalis

Cross-Links

• PubChem: 99118925
• LOTUS: LTS0145752
• wikiData: Q105188679