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

Details

• Internal ID: da68c77a-d00d-4c2e-bef6-6256d7e2ee4f
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 3-[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)chromen-4-one
• SMILES (Canonical): COC1=C(C=CC(=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)OC4C(C(C(C(O4)CO)O)O)OC5C(C(C(CO5)O)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O[C@H]4[C@@H]([C@H]([C@H]([C@H](O4)CO)O)O)O[C@H]5[C@@H]([C@H]([C@@H](CO5)O)O)O)O
• InChI: InChI=1S/C27H30O16/c1-38-14-4-9(2-3-11(14)30)23-24(20(35)17-12(31)5-10(29)6-15(17)40-23)42-27-25(21(36)19(34)16(7-28)41-27)43-26-22(37)18(33)13(32)8-39-26/h2-6,13,16,18-19,21-22,25-34,36-37H,7-8H2,1H3/t13-,16-,18+,19+,21+,22-,25-,26+,27+/m1/s1
• InChI Key: YAZLWFHAKRXSJO-CGAFZRRXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀O₁₆
• Molecular Weight: 610.50 g/mol
• Exact Mass: 610.15338487 g/mol
• Topological Polar Surface Area (TPSA): 255.00 Ų
• XlogP: -0.80
• Atomic LogP (AlogP): -1.77
• H-Bond Acceptor: 16
• 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	-	0.4761	47.61%
Caco-2	-	0.9224	92.24%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.5114	51.14%
OATP2B1 inhibitior	-	0.5763	57.63%
OATP1B1 inhibitior	+	0.8968	89.68%
OATP1B3 inhibitior	+	0.9679	96.79%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.6730	67.30%
P-glycoprotein inhibitior	-	0.5757	57.57%
P-glycoprotein substrate	+	0.5335	53.35%
CYP3A4 substrate	+	0.6842	68.42%
CYP2C9 substrate	-	0.8485	84.85%
CYP2D6 substrate	-	0.8501	85.01%
CYP3A4 inhibition	-	0.9417	94.17%
CYP2C9 inhibition	-	0.9488	94.88%
CYP2C19 inhibition	-	0.9370	93.70%
CYP2D6 inhibition	-	0.9411	94.11%
CYP1A2 inhibition	-	0.9224	92.24%
CYP2C8 inhibition	+	0.8132	81.32%
CYP inhibitory promiscuity	-	0.8596	85.96%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6677	66.77%
Eye corrosion	-	0.9915	99.15%
Eye irritation	-	0.9133	91.33%
Skin irritation	-	0.8242	82.42%
Skin corrosion	-	0.9582	95.82%
Ames mutagenesis	-	0.5128	51.28%
Human Ether-a-go-go-Related Gene inhibition	-	0.4212	42.12%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.6424	64.24%
skin sensitisation	-	0.9265	92.65%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.9368	93.68%
Acute Oral Toxicity (c)	III	0.7135	71.35%
Estrogen receptor binding	+	0.8647	86.47%
Androgen receptor binding	+	0.6252	62.52%
Thyroid receptor binding	-	0.4932	49.32%
Glucocorticoid receptor binding	+	0.6566	65.66%
Aromatase binding	+	0.6459	64.59%
PPAR gamma	+	0.7418	74.18%
Honey bee toxicity	-	0.7307	73.07%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	-	0.4193	41.93%

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	99.56%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.00%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.46%	94.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.44%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.98%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.09%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.58%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.19%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.76%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.55%	85.14%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.51%	99.15%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.98%	86.92%
CHEMBL4208	P20618	Proteasome component C5	85.83%	90.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.30%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	84.32%	94.73%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	83.60%	95.53%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	83.32%	95.83%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.20%	96.00%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	82.71%	95.78%
CHEMBL1951	P21397	Monoamine oxidase A	82.68%	91.49%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.67%	90.71%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	82.23%	95.64%
CHEMBL220	P22303	Acetylcholinesterase	82.15%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.74%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.57%	97.14%

Plants that contains it

• Glinus oppositifolius

Cross-Links

• PubChem: 162957344
• LOTUS: LTS0229990
• wikiData: Q105345724