3-[(2-O-D-Apio-beta-D-furanosyl-beta-D-glucopyranosyl)oxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

Details

• Internal ID: 8735ffd9-1db3-4f4a-8f12-4f19d8b4272a
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 3-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
• SMILES (Canonical): C1C(C(C(O1)OC2C(C(C(OC2OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC=C(C=C5)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=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC=C(C=C5)O)CO)O)O)O)(CO)O
• InChI: InChI=1S/C26H28O15/c27-7-15-17(32)19(34)22(41-25-23(35)26(36,8-28)9-37-25)24(39-15)40-21-18(33)16-13(31)5-12(30)6-14(16)38-20(21)10-1-3-11(29)4-2-10/h1-6,15,17,19,22-25,27-32,34-36H,7-9H2/t15-,17-,19+,22-,23+,24+,25+,26-/m1/s1
• InChI Key: MNBRHJWOHPGQIW-CFSZRLFJSA-N
• Popularity: 0 references 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: -0.50
• Atomic LogP (AlogP): -1.78
• H-Bond Acceptor: 15
• H-Bond Donor: 9
• Rotatable Bonds: 7

Synonyms

• 3-[(2-O-D-Apio-beta-D-furanosyl-beta-D-glucopyranosyl)oxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
• 99816-59-8

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6445	64.45%
Caco-2	-	0.9161	91.61%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.6268	62.68%
OATP2B1 inhibitior	-	0.5563	55.63%
OATP1B1 inhibitior	+	0.8840	88.40%
OATP1B3 inhibitior	+	0.9377	93.77%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8897	88.97%
P-glycoprotein inhibitior	-	0.4507	45.07%
P-glycoprotein substrate	-	0.5157	51.57%
CYP3A4 substrate	+	0.6885	68.85%
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	+	0.8077	80.77%
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	-	0.8879	88.79%
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	+	0.6751	67.51%
Micronuclear	+	0.6733	67.33%
Hepatotoxicity	-	0.5625	56.25%
skin sensitisation	-	0.8757	87.57%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.7236	72.36%
Acute Oral Toxicity (c)	III	0.5556	55.56%
Estrogen receptor binding	+	0.8110	81.10%
Androgen receptor binding	+	0.7326	73.26%
Thyroid receptor binding	+	0.5561	55.61%
Glucocorticoid receptor binding	+	0.6038	60.38%
Aromatase binding	+	0.7165	71.65%
PPAR gamma	+	0.7857	78.57%
Honey bee toxicity	-	0.6973	69.73%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.5750	57.50%
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	99.68%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.87%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.81%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.45%	94.45%
CHEMBL2581	P07339	Cathepsin D	95.05%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.83%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.20%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	91.52%	95.93%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	88.55%	86.92%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.47%	86.33%
CHEMBL242	Q92731	Estrogen receptor beta	86.89%	98.35%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.08%	99.15%
CHEMBL1937	Q92769	Histone deacetylase 2	86.05%	94.75%
CHEMBL4530	P00488	Coagulation factor XIII	85.22%	96.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.47%	99.23%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	84.37%	95.83%
CHEMBL1951	P21397	Monoamine oxidase A	83.96%	91.49%
CHEMBL3401	O75469	Pregnane X receptor	83.54%	94.73%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.52%	100.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.14%	94.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.82%	95.89%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	81.77%	95.64%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.74%	92.94%
CHEMBL4208	P20618	Proteasome component C5	81.13%	90.00%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	81.07%	80.33%
CHEMBL3922	P50579	Methionine aminopeptidase 2	80.78%	97.28%
CHEMBL6175	Q9H3R0	Lysine-specific demethylase 4C	80.37%	96.69%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	80.32%	95.53%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.27%	99.17%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	80.08%	95.78%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	80.02%	95.71%

Plants that contains it

• Solidago altissima

Cross-Links

• PubChem: 21722034
• LOTUS: LTS0001991
• wikiData: Q105168255