5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]chromen-4-one

Details

• Internal ID: 398edccf-1c54-4ea7-b6cf-6940de5d820a
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid C-glycosides
• IUPAC Name: 5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]chromen-4-one
• SMILES (Canonical): C1C(C(C(C(O1)OCC2C(C(C(C(O2)C3=C(C4=C(C=C3O)OC(=CC4=O)C5=CC=C(C=C5)O)O)O)O)O)O)O)O
• SMILES (Isomeric): C1[C@@H]([C@@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)C3=C(C4=C(C=C3O)OC(=CC4=O)C5=CC=C(C=C5)O)O)O)O)O)O)O)O
• InChI: InChI=1S/C26H28O14/c27-10-3-1-9(2-4-10)14-5-11(28)17-15(39-14)6-12(29)18(21(17)33)25-23(35)22(34)20(32)16(40-25)8-38-26-24(36)19(31)13(30)7-37-26/h1-6,13,16,19-20,22-27,29-36H,7-8H2/t13-,16+,19-,20+,22-,23+,24+,25-,26-/m0/s1
• InChI Key: FXKSMJWMDQTOGH-CCXXTZDOSA-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): 236.00 Ų
• XlogP: -1.90
• Atomic LogP (AlogP): -1.45
• H-Bond Acceptor: 14
• H-Bond Donor: 9
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4617	46.17%
Caco-2	-	0.9270	92.70%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.6348	63.48%
OATP2B1 inhibitior	-	0.5555	55.55%
OATP1B1 inhibitior	+	0.8616	86.16%
OATP1B3 inhibitior	+	0.8755	87.55%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.5735	57.35%
P-glycoprotein inhibitior	-	0.6790	67.90%
P-glycoprotein substrate	-	0.6114	61.14%
CYP3A4 substrate	+	0.6495	64.95%
CYP2C9 substrate	-	0.6762	67.62%
CYP2D6 substrate	-	0.8560	85.60%
CYP3A4 inhibition	-	0.9216	92.16%
CYP2C9 inhibition	-	0.9563	95.63%
CYP2C19 inhibition	-	0.9069	90.69%
CYP2D6 inhibition	-	0.9175	91.75%
CYP1A2 inhibition	-	0.9253	92.53%
CYP2C8 inhibition	+	0.7743	77.43%
CYP inhibitory promiscuity	-	0.8943	89.43%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6832	68.32%
Eye corrosion	-	0.9935	99.35%
Eye irritation	-	0.8983	89.83%
Skin irritation	-	0.8248	82.48%
Skin corrosion	-	0.9684	96.84%
Ames mutagenesis	+	0.6236	62.36%
Human Ether-a-go-go-Related Gene inhibition	-	0.4520	45.20%
Micronuclear	+	0.6174	61.74%
Hepatotoxicity	-	0.7375	73.75%
skin sensitisation	-	0.9031	90.31%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.9629	96.29%
Acute Oral Toxicity (c)	III	0.4775	47.75%
Estrogen receptor binding	+	0.7549	75.49%
Androgen receptor binding	+	0.7175	71.75%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.4685	46.85%
Aromatase binding	+	0.6150	61.50%
PPAR gamma	+	0.7634	76.34%
Honey bee toxicity	-	0.7175	71.75%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.8955	89.55%

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	99.79%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.04%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.95%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.84%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.20%	99.15%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.17%	97.09%
CHEMBL4040	P28482	MAP kinase ERK2	90.96%	83.82%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.02%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.81%	86.33%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	88.58%	80.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.29%	95.56%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	87.15%	83.57%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	85.75%	95.64%
CHEMBL3401	O75469	Pregnane X receptor	85.40%	94.73%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.12%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.53%	94.45%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	84.36%	91.71%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	83.42%	95.78%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.38%	95.89%
CHEMBL220	P22303	Acetylcholinesterase	81.21%	94.45%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.43%	86.92%

Plants that contains it

• Swertia perennis

Cross-Links

• PubChem: 24814097
• LOTUS: LTS0053690
• wikiData: Q105004005