2-[4-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxyphenyl]-5,7-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one

Details

• Internal ID: 5261f156-87c2-4b24-b689-7890ab6ff12f
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 2-[4-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxyphenyl]-5,7-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): C1C(C(C(O1)OC2=CC=C(C=C2)C3=C(C(=O)C4=C(C=C(C=C4O3)O)O)OC5C(C(C(C(O5)CO)O)O)O)O)(CO)O
• SMILES (Isomeric): C1[C@@]([C@H]([C@@H](O1)OC2=CC=C(C=C2)C3=C(C(=O)C4=C(C=C(C=C4O3)O)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)(CO)O
• InChI: InChI=1S/C26H28O15/c27-7-15-17(31)19(33)20(34)24(40-15)41-22-18(32)16-13(30)5-11(29)6-14(16)39-21(22)10-1-3-12(4-2-10)38-25-23(35)26(36,8-28)9-37-25/h1-6,15,17,19-20,23-25,27-31,33-36H,7-9H2/t15-,17-,19+,20-,23+,24+,25+,26-/m1/s1
• InChI Key: BBWYSXMILWHRQK-YBGCGPMFSA-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): -2.13
• 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	-	0.9213	92.13%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.6268	62.68%
OATP2B1 inhibitior	-	0.5587	55.87%
OATP1B1 inhibitior	+	0.9195	91.95%
OATP1B3 inhibitior	+	0.9377	93.77%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7175	71.75%
P-glycoprotein inhibitior	+	0.5982	59.82%
P-glycoprotein substrate	-	0.6075	60.75%
CYP3A4 substrate	+	0.6723	67.23%
CYP2C9 substrate	-	0.8271	82.71%
CYP2D6 substrate	-	0.8606	86.06%
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	+	0.8151	81.51%
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	-	0.8996	89.96%
Skin irritation	-	0.8084	80.84%
Skin corrosion	-	0.9520	95.20%
Ames mutagenesis	+	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6604	66.04%
Micronuclear	+	0.6733	67.33%
Hepatotoxicity	-	0.5573	55.73%
skin sensitisation	-	0.8757	87.57%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.6791	67.91%
Acute Oral Toxicity (c)	III	0.5556	55.56%
Estrogen receptor binding	+	0.7705	77.05%
Androgen receptor binding	+	0.6942	69.42%
Thyroid receptor binding	+	0.5200	52.00%
Glucocorticoid receptor binding	+	0.6466	64.66%
Aromatase binding	+	0.6397	63.97%
PPAR gamma	+	0.7358	73.58%
Honey bee toxicity	-	0.7137	71.37%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6150	61.50%
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	99.73%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.44%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.61%	94.00%
CHEMBL2581	P07339	Cathepsin D	95.17%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.91%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.42%	94.45%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.37%	99.15%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.32%	95.56%
CHEMBL220	P22303	Acetylcholinesterase	91.66%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.68%	86.33%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.93%	95.83%
CHEMBL3401	O75469	Pregnane X receptor	85.83%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.17%	99.23%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.01%	86.92%
CHEMBL226	P30542	Adenosine A1 receptor	84.81%	95.93%
CHEMBL4208	P20618	Proteasome component C5	84.63%	90.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.45%	92.94%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	83.60%	80.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.51%	95.89%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	83.12%	95.53%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.09%	99.17%
CHEMBL1937	Q92769	Histone deacetylase 2	82.68%	94.75%
CHEMBL4530	P00488	Coagulation factor XIII	82.57%	96.00%
CHEMBL1929	P47989	Xanthine dehydrogenase	81.56%	96.12%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	81.43%	95.78%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	80.83%	95.71%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.83%	90.71%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.00%	100.00%

Plants that contains it

• Phlomis spinidens

Cross-Links

• PubChem: 101109944
• LOTUS: LTS0126019
• wikiData: Q104923119