Licorice glycoside A

Details

• Internal ID: a1ef0d0d-f0dc-4494-8fdb-24677711aec8
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides
• IUPAC Name: [(3S,4R,5S)-5-[(2S,3R,4S,5S,6R)-2-[4-[(E)-3-(2,4-dihydroxyphenyl)-3-oxoprop-1-enyl]phenoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-3,4-dihydroxyoxolan-3-yl]methyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• SMILES (Canonical): COC1=C(C=CC(=C1)C=CC(=O)OCC2(COC(C2O)OC3C(C(C(OC3OC4=CC=C(C=C4)C=CC(=O)C5=C(C=C(C=C5)O)O)CO)O)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)/C=C/C(=O)OC[C@]2(CO[C@H]([C@@H]2O)O[C@@H]3[C@H]([C@@H]([C@H](O[C@H]3OC4=CC=C(C=C4)/C=C/C(=O)C5=C(C=C(C=C5)O)O)CO)O)O)O)O
• InChI: InChI=1S/C36H38O16/c1-47-27-14-20(5-12-25(27)40)6-13-29(42)48-17-36(46)18-49-35(33(36)45)52-32-31(44)30(43)28(16-37)51-34(32)50-22-8-2-19(3-9-22)4-11-24(39)23-10-7-21(38)15-26(23)41/h2-15,28,30-35,37-38,40-41,43-46H,16-18H2,1H3/b11-4+,13-6+/t28-,30-,31+,32-,33+,34-,35+,36-/m1/s1
• InChI Key: BYQKEKUAWGGZTQ-PMIHXJGWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₃₈O₁₆
• Molecular Weight: 726.70 g/mol
• Exact Mass: 726.21598512 g/mol
• Topological Polar Surface Area (TPSA): 251.00 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 0.62
• H-Bond Acceptor: 16
• H-Bond Donor: 8
• Rotatable Bonds: 13

Synonyms

• CHEBI:190327
• [(3S,4R,5S)-5-[(2S,3R,4S,5S,6R)-2-[4-[(E)-3-(2,4-dihydroxyphenyl)-3-oxoprop-1-enyl]phenoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-3,4-dihydroxyoxolan-3-yl]methyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6237	62.37%
Caco-2	-	0.8909	89.09%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.6245	62.45%
OATP2B1 inhibitior	-	0.7143	71.43%
OATP1B1 inhibitior	+	0.8845	88.45%
OATP1B3 inhibitior	+	0.9656	96.56%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8324	83.24%
P-glycoprotein inhibitior	+	0.6775	67.75%
P-glycoprotein substrate	+	0.5758	57.58%
CYP3A4 substrate	+	0.7027	70.27%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8708	87.08%
CYP3A4 inhibition	-	0.8295	82.95%
CYP2C9 inhibition	-	0.8438	84.38%
CYP2C19 inhibition	-	0.8509	85.09%
CYP2D6 inhibition	-	0.9111	91.11%
CYP1A2 inhibition	-	0.9006	90.06%
CYP2C8 inhibition	+	0.8137	81.37%
CYP inhibitory promiscuity	-	0.8129	81.29%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5549	55.49%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.9163	91.63%
Skin irritation	-	0.8289	82.89%
Skin corrosion	-	0.9388	93.88%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7480	74.80%
Micronuclear	+	0.5433	54.33%
Hepatotoxicity	-	0.7216	72.16%
skin sensitisation	-	0.8047	80.47%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.8994	89.94%
Acute Oral Toxicity (c)	III	0.7205	72.05%
Estrogen receptor binding	+	0.8237	82.37%
Androgen receptor binding	+	0.6304	63.04%
Thyroid receptor binding	+	0.5407	54.07%
Glucocorticoid receptor binding	+	0.6008	60.08%
Aromatase binding	+	0.5884	58.84%
PPAR gamma	+	0.7326	73.26%
Honey bee toxicity	-	0.6936	69.36%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.8142	81.42%

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	99.80%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.80%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.77%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.97%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.12%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.85%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.69%	96.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.47%	94.45%
CHEMBL4208	P20618	Proteasome component C5	93.74%	90.00%
CHEMBL3194	P02766	Transthyretin	91.78%	90.71%
CHEMBL3714130	P46095	G-protein coupled receptor 6	90.97%	97.36%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.02%	99.17%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	89.36%	91.07%
CHEMBL241	Q14432	Phosphodiesterase 3A	88.44%	92.94%
CHEMBL2243	O00519	Anandamide amidohydrolase	88.03%	97.53%
CHEMBL226	P30542	Adenosine A1 receptor	85.37%	95.93%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	84.58%	89.62%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.45%	94.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.43%	94.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.48%	97.14%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.23%	95.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.91%	95.89%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.70%	95.89%
CHEMBL3922	P50579	Methionine aminopeptidase 2	81.83%	97.28%
CHEMBL206	P03372	Estrogen receptor alpha	80.03%	97.64%

Plants that contains it

• Glycyrrhiza glabra
• Glycyrrhiza inflata
• Glycyrrhiza uralensis
• Mitracarpus hirtus

Cross-Links

• PubChem: 101938903
• NPASS: NPC43450