Natural Product (NP) Details

General Information of the NP (ID: NP9253)
Name
Liquiritin
Synonyms
Liquiritin; Liquiritoside; 551-15-5; 7-Hydroxyflavanone 4'-O-glucoside; Likviritin; UNII-T0O79T74CD; CHEBI:80845; T0O79T74CD; 4',7-Dihydroxyflavanone 4'-(beta-D-glucopyranoside); (2S)-7-hydroxy-2-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxyphenyl]chroman-4-one; 4'-O-beta-D-glucopyranosyl-7-hydroxyflavan-4-one; Likviriton; 4H-1-Benzopyran-4-one,2-[4-(b-D-glucopyranosyloxy)phenyl]-2,3-dihydro-7-hydroxy-, (2S)-; (S)-7-hydroxy-2-(4-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)chroman-4-one; 4',7-Dihydroxyflavanone 4'-(beta-D-glucoside); Liquiritigenin-4'-O-glucoside; MLS000575018; CHEMBL511995; Liquiritigenin-4'-beta-glucoside; DTXSID40203619; HMS2214B11; liquiritigenin-4'-beta-D-glucoside; HY-N0376; ZINC8829785; BDBM50479044; MFCD00210526; s3930; AKOS015897117; CCG-268869; (S)-2-(4-(beta-D-Glucopyranosyloxy)phenyl)-2,3-dihydro-7-hydroxy-4H-1-benzopyran-4-one; AS-74201; AT-22713; SMR000232362; 7-hydroxyflavanone 4'-O-beta-D-glucoside; liquiritigenin 4'-O-beta-D-glucopyranoside; CS-0008920; X1173; A12084; C16989; Q-100625; Q3242316; Liquiritin, from Glycyrrhizae root (licorice root), >=98% (HPLC); 4-[(2S)-7-hydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl]phenyl beta-D-glucopyranoside; (2S)-7-hydroxy-2-(4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3,4-dihydro-2H-1-benzopyran-4-one; (S)-7-hydroxy-2-(4-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)phenyl)chroman-4-one; (S)-7-Hydroxy-2-[4-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-chroman-4-one; 4H-1-Benzopyran-4-one, 2-(4-(beta-D-glucopyranosyloxy)phenyl)-2,3-dihydro-7-hydroxy-, (S)-
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Species Origin Glycyrrhiza uralensis ...     Click to Show/Hide
Glycyrrhiza uralensis
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Fabales
Family: Fabaceae
Genus: Glycyrrhiza
Species: Glycyrrhiza uralensis
Disease Rheumatoid arthritis [ICD-11: FA20] Investigative [1]
Structure
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2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -6.623
 
MDCK Permeability
 -4.989
 
PAMPA
 +++
 
HIA
 - -
 
Distribution
VDss
 -0.215
 
PPB
 90%
 
BBB
 - - -
 
Metabolism
CYP1A2 inhibitor
 - - -
CYP1A2 substrate
 - - -
CYP2C19 inhibitor
 - - -
CYP2C19 substrate
 - - -
CYP2C9 inhibitor
 - - -
CYP2C9 substrate
 - - -
CYP2D6 inhibitor
 - - -
CYP2D6 substrate
 - - -
CYP3A4 inhibitor
 - -
CYP3A4 substrate
 - - -
CYP2B6 inhibitor
 - - -
CYP2B6 substrate
 - - -
CYP2C8 inhibitor
 - -
HLM Stability
 - -
 
Excretion
CLplasma
 2.502
 
T1/2
 3.697
Toxicity
DILI
 +++
 
Rat Oral Acute Toxicity
 - - -
 
FDAMDD
 - - -
 
Respiratory
 - - -
 
Human Hepatotoxicity
 ++
 
Ototoxicity
 ++
 
Drug-induced Nephrotoxicity
 ++
 
Drug-induced Neurotoxicity
 - - -
 
Hematotoxicity
 - -
 
Genotoxicity
 +++
 
Tips: 1. For the classification endpoints, the prediction probability values are transformed into six symbols: 0-0.1 (- - -), 0.1-0.3 (- -), 0.3-0.5 (-), 0.5-0.7 (+), 0.7-0.9 (++), and 0.9-1.0 (+++). 2. Additionally, the corresponding relationships of the three labels are as follows: excellent; medium; poor.
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Formula
C21H22O9
PubChem CID
503737
Canonical SMILES
C1C(OC2=C(C1=O)C=CC(=C2)O)C3=CC=C(C=C3)OC4C(C(C(C(O4)CO)O)O)O
InChI
1S/C21H22O9/c22-9-17-18(25)19(26)20(27)21(30-17)28-12-4-1-10(2-5-12)15-8-14(24)13-6-3-11(23)7-16(13)29-15/h1-7,15,17-23,25-27H,8-9H2/t15-,17+,18+,19-,20+,21+/m0/s1
InChIKey
DEMKZLAVQYISIA-ZRWXNEIDSA-N
CAS Number
CAS 551-15-5
ChEBI ID
CHEBI:80845
Herb ID
HBIN033383
SymMap ID
SMIT00217
TCMSP ID
MOL004903
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          TNF-related apoptosis inducing ligand      Lung cancer     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Biological
                    Regulation		 Induction Apoptosis
Induction ROS generation
                    In-vitro Model AGS CVCL_0139 Gastric adenocarcinoma Homo sapiens
SNU-216 CVCL_3946 Gastric tubular adenocarcinoma Homo sapiens
                    Experimental
                    Result(s)		 In combination, the two drugs functioned synergistically to impede the progression and growth of human gastric cancer cells in vitro and gastric cancer cell xenograft nude mice in vivo.
References
Reference 1 Liquiritin from Glycyrrhiza uralensis Attenuating Rheumatoid Arthritis via Reducing Inflammation, Suppressing Angiogenesis, and Inhibiting MAPK Signaling Pathway. J Agric Food Chem. 2019 Mar 13;67(10):2856-2864.
Reference 2 Combining TRAIL and liquiritin exerts synergistic effects against human gastric cancer cells and xenograft in nude mice through potentiating apoptosis and ROS generation. Biomed Pharmacother. 2017 Sep;93:948-960.
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