3-[(2S,3S,4S,5S,6R)-6-[[(2R,3S,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-[(2S,3S,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)chromen-4-one

Details

• Internal ID: 033c0863-61c3-4c06-8f64-21b0ce982bf9
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 3-[(2S,3S,4S,5S,6R)-6-[[(2R,3S,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-[(2S,3S,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)chromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC(=C(C=C5)O)OC)O)O)O)O)OC6C(C(C(CO6)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@@H]([C@@H](O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC(=C(C=C5)O)OC)O)O)O)O)O[C@H]6[C@H]([C@H]([C@H](CO6)O)O)O)O
• InChI: InChI=1S/C33H40O20/c1-10-20(38)29(52-31-25(43)21(39)15(37)8-47-31)27(45)32(49-10)48-9-18-22(40)24(42)26(44)33(51-18)53-30-23(41)19-14(36)6-12(34)7-17(19)50-28(30)11-3-4-13(35)16(5-11)46-2/h3-7,10,15,18,20-22,24-27,29,31-40,42-45H,8-9H2,1-2H3/t10-,15-,18+,20-,21-,22+,24-,25-,26-,27-,29+,31-,32+,33-/m0/s1
• InChI Key: GUDFTJNDUNRMLG-GIUIMVCRSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₄₀O₂₀
• Molecular Weight: 756.70 g/mol
• Exact Mass: 756.21129366 g/mol
• Topological Polar Surface Area (TPSA): 313.00 Ų
• XlogP: -2.50
• Atomic LogP (AlogP): -2.92
• H-Bond Acceptor: 20
• H-Bond Donor: 11
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4594	45.94%
Caco-2	-	0.9000	90.00%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.5851	58.51%
OATP2B1 inhibitior	-	0.7167	71.67%
OATP1B1 inhibitior	+	0.8824	88.24%
OATP1B3 inhibitior	+	0.9495	94.95%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.5996	59.96%
P-glycoprotein inhibitior	-	0.4357	43.57%
P-glycoprotein substrate	+	0.7085	70.85%
CYP3A4 substrate	+	0.6861	68.61%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8527	85.27%
CYP3A4 inhibition	-	0.9206	92.06%
CYP2C9 inhibition	-	0.9461	94.61%
CYP2C19 inhibition	-	0.9332	93.32%
CYP2D6 inhibition	-	0.9275	92.75%
CYP1A2 inhibition	-	0.9269	92.69%
CYP2C8 inhibition	+	0.8331	83.31%
CYP inhibitory promiscuity	-	0.8326	83.26%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6686	66.86%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9083	90.83%
Skin irritation	-	0.8326	83.26%
Skin corrosion	-	0.9576	95.76%
Ames mutagenesis	-	0.5828	58.28%
Human Ether-a-go-go-Related Gene inhibition	-	0.4268	42.68%
Micronuclear	+	0.7233	72.33%
Hepatotoxicity	-	0.5674	56.74%
skin sensitisation	-	0.9301	93.01%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.9675	96.75%
Acute Oral Toxicity (c)	III	0.7494	74.94%
Estrogen receptor binding	+	0.7979	79.79%
Androgen receptor binding	+	0.5696	56.96%
Thyroid receptor binding	-	0.4919	49.19%
Glucocorticoid receptor binding	+	0.6310	63.10%
Aromatase binding	+	0.5782	57.82%
PPAR gamma	+	0.7194	71.94%
Honey bee toxicity	-	0.7216	72.16%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.7604	76.04%

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%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.96%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.60%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.09%	94.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.59%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.51%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	95.96%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.72%	95.56%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	89.55%	95.64%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.76%	99.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.41%	99.15%
CHEMBL4208	P20618	Proteasome component C5	87.56%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.98%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	85.38%	94.73%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.31%	90.71%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.77%	92.94%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.08%	85.14%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	83.54%	95.53%
CHEMBL3714130	P46095	G-protein coupled receptor 6	83.39%	97.36%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.13%	97.09%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	83.10%	95.78%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.71%	96.00%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	81.63%	94.03%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.54%	86.92%

Plants that contains it

• Haloxylon scoparium

Cross-Links

• PubChem: 163099535
• LOTUS: LTS0045728
• wikiData: Q105020018