(3S)-5-[[(2R,3R,4S,5R,6S)-5-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-6-[2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-4-oxochromen-3-yl]oxy-3,4-dihydroxyoxan-2-yl]methoxy]-3-hydroxy-3-methyl-5-oxopentanoic acid

Details

• Internal ID: 5f98d06c-6503-4128-bab1-90fecd85c0db
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: (3S)-5-[[(2R,3R,4S,5R,6S)-5-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-6-[2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-4-oxochromen-3-yl]oxy-3,4-dihydroxyoxan-2-yl]methoxy]-3-hydroxy-3-methyl-5-oxopentanoic acid
• SMILES (Canonical): CC(CC(=O)O)(CC(=O)OCC1C(C(C(C(O1)OC2=C(OC3=CC(=CC(=C3C2=O)O)OC)C4=CC(=C(C=C4)O)O)OC5C(C(CO5)(CO)O)O)O)O)O
• SMILES (Isomeric): C[C@](CC(=O)O)(CC(=O)OC[C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)OC2=C(OC3=CC(=CC(=C3C2=O)O)OC)C4=CC(=C(C=C4)O)O)O[C@H]5[C@@H]([C@](CO5)(CO)O)O)O)O)O
• InChI: InChI=1S/C33H38O20/c1-32(45,8-20(38)39)9-21(40)48-10-19-23(41)25(43)28(53-31-29(44)33(46,11-34)12-49-31)30(51-19)52-27-24(42)22-17(37)6-14(47-2)7-18(22)50-26(27)13-3-4-15(35)16(36)5-13/h3-7,19,23,25,28-31,34-37,41,43-46H,8-12H2,1-2H3,(H,38,39)/t19-,23+,25+,28-,29+,30+,31+,32+,33-/m1/s1
• InChI Key: LBWBQACKWAITFN-UYCSNVJISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₃₈O₂₀
• Molecular Weight: 754.60 g/mol
• Exact Mass: 754.19564360 g/mol
• Topological Polar Surface Area (TPSA): 318.00 Ų
• XlogP: -1.50
• Atomic LogP (AlogP): -1.60
• H-Bond Acceptor: 19
• H-Bond Donor: 10
• Rotatable Bonds: 13

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6660	66.60%
Caco-2	-	0.8812	88.12%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.6169	61.69%
OATP2B1 inhibitior	-	0.7200	72.00%
OATP1B1 inhibitior	+	0.8717	87.17%
OATP1B3 inhibitior	+	0.9648	96.48%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8134	81.34%
P-glycoprotein inhibitior	+	0.7024	70.24%
P-glycoprotein substrate	+	0.6313	63.13%
CYP3A4 substrate	+	0.7268	72.68%
CYP2C9 substrate	-	0.6399	63.99%
CYP2D6 substrate	-	0.8692	86.92%
CYP3A4 inhibition	-	0.7839	78.39%
CYP2C9 inhibition	-	0.8896	88.96%
CYP2C19 inhibition	-	0.8711	87.11%
CYP2D6 inhibition	-	0.9331	93.31%
CYP1A2 inhibition	-	0.8918	89.18%
CYP2C8 inhibition	+	0.8159	81.59%
CYP inhibitory promiscuity	-	0.8814	88.14%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5503	55.03%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9142	91.42%
Skin irritation	-	0.8185	81.85%
Skin corrosion	-	0.9427	94.27%
Ames mutagenesis	+	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7873	78.73%
Micronuclear	+	0.6200	62.00%
Hepatotoxicity	+	0.5750	57.50%
skin sensitisation	-	0.8852	88.52%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.9458	94.58%
Acute Oral Toxicity (c)	III	0.5956	59.56%
Estrogen receptor binding	+	0.8043	80.43%
Androgen receptor binding	+	0.7202	72.02%
Thyroid receptor binding	+	0.5170	51.70%
Glucocorticoid receptor binding	+	0.6942	69.42%
Aromatase binding	+	0.6480	64.80%
PPAR gamma	+	0.7313	73.13%
Honey bee toxicity	-	0.7142	71.42%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9394	93.94%

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	99.83%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.70%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.53%	89.00%
CHEMBL2581	P07339	Cathepsin D	97.17%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	96.75%	99.15%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.84%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.47%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.46%	86.33%
CHEMBL226	P30542	Adenosine A1 receptor	94.15%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.55%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.16%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.80%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.14%	99.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.87%	99.23%
CHEMBL220	P22303	Acetylcholinesterase	88.32%	94.45%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	87.97%	94.33%
CHEMBL3401	O75469	Pregnane X receptor	87.40%	94.73%
CHEMBL340	P08684	Cytochrome P450 3A4	87.20%	91.19%
CHEMBL3714130	P46095	G-protein coupled receptor 6	85.65%	97.36%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.12%	86.92%
CHEMBL1951	P21397	Monoamine oxidase A	84.48%	91.49%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.64%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	82.79%	92.50%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	81.70%	95.71%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.43%	97.14%
CHEMBL3922	P50579	Methionine aminopeptidase 2	80.14%	97.28%

Plants that contains it

• Astragalus caprinus

Cross-Links

• PubChem: 163026497
• LOTUS: LTS0102502
• wikiData: Q105149672