2-(3,4-dihydroxyphenyl)-5-hydroxy-6-[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-7-[(2S,3S,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxychromen-4-one

Details

• Internal ID: ef82cef5-6a92-48dd-8767-91ee1f135c48
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 2-(3,4-dihydroxyphenyl)-5-hydroxy-6-[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-7-[(2S,3S,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxychromen-4-one
• SMILES (Canonical): C1C(C(C(C(O1)OC2=C(C(=C3C(=C2)OC(=CC3=O)C4=CC(=C(C=C4)O)O)O)C5C(C(C(C(O5)CO)O)O)O)O)O)O
• SMILES (Isomeric): C1[C@H]([C@@H]([C@@H]([C@@H](O1)OC2=C(C(=C3C(=C2)OC(=CC3=O)C4=CC(=C(C=C4)O)O)O)[C@H]5[C@@H]([C@H]([C@@H]([C@@H](O5)CO)O)O)O)O)O)O
• InChI: InChI=1S/C26H28O15/c27-6-16-20(33)22(35)23(36)25(40-16)18-15(41-26-24(37)19(32)12(31)7-38-26)5-14-17(21(18)34)11(30)4-13(39-14)8-1-2-9(28)10(29)3-8/h1-5,12,16,19-20,22-29,31-37H,6-7H2/t12-,16+,19+,20-,22+,23-,24+,25+,26+/m1/s1
• InChI Key: ULWMURRUKFUJTH-WBVDAKISSA-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): 256.00 Ų
• XlogP: -1.90
• Atomic LogP (AlogP): -2.09
• H-Bond Acceptor: 15
• H-Bond Donor: 10
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5110	51.10%
Caco-2	-	0.9327	93.27%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.4988	49.88%
OATP2B1 inhibitior	-	0.5554	55.54%
OATP1B1 inhibitior	+	0.8728	87.28%
OATP1B3 inhibitior	+	0.9174	91.74%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.5797	57.97%
P-glycoprotein inhibitior	-	0.6226	62.26%
P-glycoprotein substrate	-	0.5772	57.72%
CYP3A4 substrate	+	0.6425	64.25%
CYP2C9 substrate	-	0.6621	66.21%
CYP2D6 substrate	-	0.8575	85.75%
CYP3A4 inhibition	-	0.9373	93.73%
CYP2C9 inhibition	-	0.9644	96.44%
CYP2C19 inhibition	-	0.9395	93.95%
CYP2D6 inhibition	-	0.9332	93.32%
CYP1A2 inhibition	-	0.9304	93.04%
CYP2C8 inhibition	+	0.7269	72.69%
CYP inhibitory promiscuity	-	0.8779	87.79%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6882	68.82%
Eye corrosion	-	0.9940	99.40%
Eye irritation	-	0.8904	89.04%
Skin irritation	-	0.8205	82.05%
Skin corrosion	-	0.9667	96.67%
Ames mutagenesis	+	0.6372	63.72%
Human Ether-a-go-go-Related Gene inhibition	+	0.7353	73.53%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.7821	78.21%
skin sensitisation	-	0.9071	90.71%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.9694	96.94%
Acute Oral Toxicity (c)	III	0.4508	45.08%
Estrogen receptor binding	+	0.7656	76.56%
Androgen receptor binding	+	0.6982	69.82%
Thyroid receptor binding	+	0.5143	51.43%
Glucocorticoid receptor binding	-	0.5775	57.75%
Aromatase binding	+	0.5744	57.44%
PPAR gamma	+	0.7444	74.44%
Honey bee toxicity	-	0.6417	64.17%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6749	67.49%
Fish aquatic toxicity	+	0.7253	72.53%

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	99.89%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.46%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.26%	89.00%
CHEMBL220	P22303	Acetylcholinesterase	95.22%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.88%	94.00%
CHEMBL1951	P21397	Monoamine oxidase A	94.11%	91.49%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.05%	99.15%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	93.00%	96.21%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.57%	97.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	88.66%	86.92%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.32%	95.56%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	86.78%	90.71%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.90%	85.14%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	84.16%	95.83%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.78%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	83.41%	94.73%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.11%	95.89%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.02%	96.09%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	82.21%	95.78%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	81.76%	80.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.25%	94.45%

Plants that contains it

• Vellozia glabra

Cross-Links

• PubChem: 163001033
• LOTUS: LTS0080398
• wikiData: Q105275393