Licuraside

Details

• Internal ID: 973369fa-0a4c-49a4-a4ca-2c3a0e313124
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides
• IUPAC Name: (E)-1-[4-[(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-2-hydroxyphenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
• SMILES (Canonical): C1C(C(C(O1)OC2C(C(C(OC2OC3=CC(=C(C=C3)C(=O)C=CC4=CC=C(C=C4)O)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=CC(=C(C=C3)C(=O)/C=C/C4=CC=C(C=C4)O)O)CO)O)O)O)(CO)O
• InChI: InChI=1S/C26H30O13/c27-10-19-20(32)21(33)22(39-25-23(34)26(35,11-28)12-36-25)24(38-19)37-15-6-7-16(18(31)9-15)17(30)8-3-13-1-4-14(29)5-2-13/h1-9,19-25,27-29,31-35H,10-12H2/b8-3+/t19-,20-,21+,22-,23+,24-,25+,26-/m1/s1
• InChI Key: NIZFPXZQERMCLE-KVFWHIKKSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₀O₁₃
• Molecular Weight: 550.50 g/mol
• Exact Mass: 550.16864101 g/mol
• Topological Polar Surface Area (TPSA): 216.00 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): -1.36
• H-Bond Acceptor: 13
• H-Bond Donor: 8
• Rotatable Bonds: 9

Synonyms

• Licuraside
• Liquirazide
• Licurazid
• 29913-71-1
• UNII-3UT49C2OHM
• 3UT49C2OHM
• CHEMBL1940910
• 2-Propen-1-one, 1-(4-((2-o-D-apio-beta-D-furanosyl-beta-D-glucopyranosyl)oxy)-2-hydroxyphenyl)-3-(4-hydroxyphenyl)-, (2E)-
• (E)-1-(4-(((2S,3R,4S,5S,6R)-3-(((2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)tetrahydrofuran-2-yl)oxy)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-2-hydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
• (E)-1-[4-[(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-2-hydroxyphenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
• HY-N6987
• BDBM50362888
• AKOS040741953
• MS-30069
• CS-0101434
• D84916
• Q27258053
• 1-[4-[(2-O-D-Apio-beta-D-furanosyl-beta-D-glucopyranosyl)oxy]-2-hydroxyphenyl]-3-(4-hydroxyphenyl)propenal
• 2-PROPEN-1-ONE, 1-(4-((2-O-D-APIO-.BETA.-D-FURANOSYL-.BETA.-D-GLUCOPYRANOSYL)OXY)-2-HYDROXYPHENYL)-3-(4-HYDROXYPHENYL)-, (2E)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5825	58.25%
Caco-2	-	0.9150	91.50%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.6707	67.07%
OATP2B1 inhibitior	-	0.5667	56.67%
OATP1B1 inhibitior	+	0.9151	91.51%
OATP1B3 inhibitior	+	0.9534	95.34%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.7721	77.21%
P-glycoprotein inhibitior	-	0.5657	56.57%
P-glycoprotein substrate	-	0.6980	69.80%
CYP3A4 substrate	+	0.6451	64.51%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8683	86.83%
CYP3A4 inhibition	-	0.8390	83.90%
CYP2C9 inhibition	-	0.8898	88.98%
CYP2C19 inhibition	-	0.8493	84.93%
CYP2D6 inhibition	-	0.8673	86.73%
CYP1A2 inhibition	-	0.9016	90.16%
CYP2C8 inhibition	+	0.6654	66.54%
CYP inhibitory promiscuity	-	0.7165	71.65%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5805	58.05%
Eye corrosion	-	0.9929	99.29%
Eye irritation	-	0.9109	91.09%
Skin irritation	-	0.8203	82.03%
Skin corrosion	-	0.9473	94.73%
Ames mutagenesis	+	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3693	36.93%
Micronuclear	+	0.5133	51.33%
Hepatotoxicity	-	0.7250	72.50%
skin sensitisation	-	0.7750	77.50%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.6889	68.89%
Acute Oral Toxicity (c)	III	0.6726	67.26%
Estrogen receptor binding	+	0.7578	75.78%
Androgen receptor binding	+	0.6169	61.69%
Thyroid receptor binding	+	0.5445	54.45%
Glucocorticoid receptor binding	-	0.5255	52.55%
Aromatase binding	+	0.7217	72.17%
PPAR gamma	+	0.7712	77.12%
Honey bee toxicity	-	0.7025	70.25%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.8516	85.16%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1900	P15121	Aldose reductase	560 nM; 560 nM	IC50; IC50	via Super-PRED; PMID: 22261024

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.61%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	96.97%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.20%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.25%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.64%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.48%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.62%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	90.41%	96.00%
CHEMBL4208	P20618	Proteasome component C5	89.27%	90.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	88.98%	91.07%
CHEMBL3194	P02766	Transthyretin	88.51%	90.71%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.36%	96.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.33%	92.94%
CHEMBL3714130	P46095	G-protein coupled receptor 6	85.93%	97.36%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.13%	99.17%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	84.94%	85.00%
CHEMBL2243	O00519	Anandamide amidohydrolase	84.20%	97.53%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.91%	94.33%
CHEMBL206	P03372	Estrogen receptor alpha	82.62%	97.64%
CHEMBL2581	P07339	Cathepsin D	82.24%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.16%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	81.74%	94.73%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.43%	95.89%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	81.21%	91.24%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.48%	95.83%

Plants that contains it

• Glycyrrhiza
• Glycyrrhiza uralensis
• Glycyrrhiza uralensis
• Mitracarpus hirtus

Cross-Links

• PubChem: 14282455
• NPASS: NPC265480
• ChEMBL: CHEMBL1940910
• LOTUS: LTS0190017
• wikiData: Q27258053