NP-MRD: Showing NP-Card for Liquiritin (NP0044057)

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Record Information

Version

1.0

Created at

2021-11-12 23:47:37 UTC

Updated at

2021-11-26 17:44:57 UTC

NP-MRD ID

NP0044057

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Liquiritin

Description

Liquiritin, also known as likviriton, belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. Liquiritin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Liquiritin is found in Apis cerana, Artemisia capillaris, Tetradium glabrifolium, Glycyrrhiza aspera, Glycyrrhiza glabra , Glycyrrhiza inflata , Glycyrrhiza kansuensis, Glycyrrhiza spp., Glycyrrhiza uralensis , Polygonum aviculare and Portulaca oleracea. It was first documented in 2005 (PMID: 16159166). Based on a literature review a significant number of articles have been published on liquiritin (PMID: 34731782) (PMID: 34721339) (PMID: 34655988) (PMID: 34582913).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652311132100472D          

 30 33  0  0  1  0            999 V2000
   -0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    3.3000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  6  8  1  1  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 13 22  1  0  0  0  0
 22 23  1  1  0  0  0
 11 24  1  0  0  0  0
 24 25  2  0  0  0  0
  8 25  1  0  0  0  0
  4 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 29 30  1  0  0  0  0
  3 30  2  0  0  0  0
M  END

     RDKit          3D

 52 55  0  0  0  0  0  0  0  0999 V2000
    4.5003    2.8197   -1.1197 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4877    2.0541   -0.1213 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0628    2.5089    1.2282 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3063    1.4029    1.9464 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9625    1.1521    1.3750 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2479    0.0168    1.7614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0033   -0.2677    1.2574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6313    0.5457    0.3417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8838    0.3094   -0.1964 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7491   -0.7451    0.0502 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0154   -1.5245   -1.0568 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0387   -1.1520   -1.8634 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7415   -0.0132   -2.8052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3817    1.1552   -2.1921 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3424   -0.8983   -1.1333 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.3904   -1.6630   -1.6062 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1413   -1.0947    0.3780 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.3099   -0.6608    1.0163 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9778   -0.1954    0.7350 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8085   -0.2326    2.1120 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0838    1.6852   -0.0475 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3350    1.9632    0.4609 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0968    0.1916    1.8866 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6984   -0.2278    0.7165 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1010   -1.5556    0.5455 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7001   -1.9692   -0.6220 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0822   -3.3202   -0.7313 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9168   -1.0791   -1.6519 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5099    0.2230   -1.4555 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9051    0.6709   -0.2949 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0044    2.7315    1.8168 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4266    3.3945    1.1909 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2898    1.6758    3.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7413   -0.6340    2.4890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5035   -1.1657    1.5996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2819   -1.4299    0.7862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2514   -2.0410   -2.5337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6683    0.1200   -3.4368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9467   -0.2751   -3.5355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2178    1.6378   -1.9245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6239    0.1683   -1.2549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2603   -1.2392   -1.4659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8799   -2.1262    0.6206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4963   -1.2989    1.7344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2445    0.8257    0.3943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1354    0.5922    2.5488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4042    2.3342   -0.7708 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8628    2.8724    0.1218 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9271   -2.2461    1.3582 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0325   -3.5706   -0.4188 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3914   -1.4007   -2.5804 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6563    0.9753   -2.2394 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2 30  1  0
 30 24  2  0
 24 23  1  0
 23  4  1  0
  4  3  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
  8 21  1  0
 21 22  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  2  0
  3  2  1  0
 30 29  1  0
 22  5  1  0
 19 10  1  0
  4 33  1  1
  3 31  1  0
  3 32  1  0
  6 34  1  0
  7 35  1  0
 10 36  1  1
 12 37  1  6
 13 38  1  0
 13 39  1  0
 14 40  1  0
 15 41  1  1
 16 42  1  0
 17 43  1  6
 18 44  1  0
 19 45  1  6
 20 46  1  0
 21 47  1  0
 22 48  1  0
 25 49  1  0
 27 50  1  0
 28 51  1  0
 29 52  1  0
M  END


  Mrv1652311132100472D          

 30 33  0  0  1  0            999 V2000
   -0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    3.3000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  6  8  1  1  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 13 22  1  0  0  0  0
 22 23  1  1  0  0  0
 11 24  1  0  0  0  0
 24 25  2  0  0  0  0
  8 25  1  0  0  0  0
  4 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 29 30  1  0  0  0  0
  3 30  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0044057

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=CC=C(C=C2)[C@@H]2CC(=O)C3=CC=C(O)C=C3O2)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
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

> <INCHI_KEY>
DEMKZLAVQYISIA-ZRWXNEIDSA-N

> <FORMULA>
C21H22O9

> <MOLECULAR_WEIGHT>
418.398

> <EXACT_MASS>
418.126382288

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
40.78744570049187

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(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

> <ALOGPS_LOGP>
0.43

> <JCHEM_LOGP>
0.22060527866666677

> <ALOGPS_LOGS>
-2.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.199625329703442

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.79795829496719

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092343686494

> <JCHEM_POLAR_SURFACE_AREA>
145.91000000000003

> <JCHEM_REFRACTIVITY>
101.45330000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.79e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-7-hydroxy-2-(4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-NOV-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-NOV-21         0                                  
HETATM    1  O   UNK     0      -0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.000  -0.000   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -6.668   2.310   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -8.002   4.620   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -8.002   6.160   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -9.336   6.930   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -9.336   8.470   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -6.668   6.930   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -6.668   8.470   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -4.001   6.930   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -4.001   3.850   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.335  -0.000   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4   30                                                  
CONECT    4    3    5   26                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6    2                                                       
CONECT    8    6    9   25                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   24                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   22                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   13   23                                                  
CONECT   23   22                                                            
CONECT   24   11   25                                                       
CONECT   25   24    8                                                       
CONECT   26    4   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29    3                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Value	Source
4',7-Dihydroxyflavanone 4'-(beta-D-glucopyranoside)	ChEBI
4'-O-beta-D-Glucopyranosyl-7-hydroxyflavan-4-one	ChEBI
7-Hydroxyflavanone 4'-O-beta-D-glucoside	ChEBI
7-Hydroxyflavanone 4'-O-glucoside	ChEBI
Likviritin	ChEBI
Liquiritigenin 4'-O-beta-D-glucopyranoside	ChEBI
Liquiritigenin-4'-beta-D-glucoside	ChEBI
Liquiritoside	ChEBI
Liquiritigenin-4'-beta-glucoside	Kegg
4',7-Dihydroxyflavanone 4'-(b-D-glucopyranoside)	Generator
4',7-Dihydroxyflavanone 4'-(β-D-glucopyranoside)	Generator
4'-O-b-D-Glucopyranosyl-7-hydroxyflavan-4-one	Generator
4'-O-Β-D-glucopyranosyl-7-hydroxyflavan-4-one	Generator
7-Hydroxyflavanone 4'-O-b-D-glucoside	Generator
7-Hydroxyflavanone 4'-O-β-D-glucoside	Generator
Liquiritigenin 4'-O-b-D-glucopyranoside	Generator
Liquiritigenin 4'-O-β-D-glucopyranoside	Generator
Liquiritigenin-4'-b-D-glucoside	Generator
Liquiritigenin-4'-β-D-glucoside	Generator
Liquiritigenin-4'-b-glucoside	Generator
Liquiritigenin-4'-β-glucoside	Generator
Likviriton	MeSH

Chemical Formula

C₂₁H₂₂O₉

Average Mass

418.3980 Da

Monoisotopic Mass

418.12638 Da

IUPAC Name

(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

Traditional Name

(2S)-7-hydroxy-2-(4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-2,3-dihydro-1-benzopyran-4-one

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC2=CC=C(C=C2)[C@@H]2CC(=O)C3=CC=C(O)C=C3O2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

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

InChI Key

DEMKZLAVQYISIA-ZRWXNEIDSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Apis cerana	LOTUS Database	35616633
Artemisia capillaris	LOTUS Database	35616633
Euodia fargesii	LOTUS Database	35616633
Glycyrrhiza aspera	Plant	KNApSAcK
Glycyrrhiza glabra	Plant	KNApSAcK
Glycyrrhiza inflata	Plant	KNApSAcK
Glycyrrhiza kansuensis	Plant	KNApSAcK
Glycyrrhiza spp.	Plant	KNApSAcK
Glycyrrhiza uralensis	Plant	KNApSAcK
Polygonum aviculare	LOTUS Database	35616633
Portulaca oleracea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid O-glycosides

Alternative Parents

Substituents

Flavonoid-4p-o-glycoside
Flavonoid o-glycoside
7-hydroxyflavonoid
Flavanone
Hydroxyflavonoid
Flavan
Phenolic glycoside
Hexose monosaccharide
Chromone
Glycosyl compound
O-glycosyl compound
Chromane
Benzopyran
1-benzopyran
Phenoxy compound
Aryl alkyl ketone
Aryl ketone
Phenol ether
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Oxane
Monocyclic benzene moiety
Monosaccharide
Benzenoid
Secondary alcohol
Ketone
Acetal
Organoheterocyclic compound
Oxacycle
Ether
Polyol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Primary alcohol
Alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

beta-D-glucoside (CHEBI:80845 )
monosaccharide derivative (CHEBI:80845 )
monohydroxyflavanone (CHEBI:80845 )
flavanone glycoside (CHEBI:80845 )
flavanones (C16989 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.43	ALOGPS
logP	0.22	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	7.8	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	145.91 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	101.45 m³·mol⁻¹	ChemAxon
Polarizability	40.79 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Liquiritin

METLIN ID

Not Available

PubChem Compound

503737

PDB ID

Not Available

ChEBI ID

80845

Good Scents ID

rw1810161

References

General References

Fu B, Li H, Wang X, Lee FS, Cui S: Isolation and identification of flavonoids in licorice and a study of their inhibitory effects on tyrosinase. J Agric Food Chem. 2005 Sep 21;53(19):7408-14. doi: 10.1021/jf051258h. [PubMed:16159166 ]
Yang X, Dang X, Zhang X, Zhao S: Liquiritin reduces lipopolysaccharide-aroused HaCaT cell inflammation damage via regulation of microRNA-31/MyD88. Int Immunopharmacol. 2021 Oct 30;101(Pt B):108283. doi: 10.1016/j.intimp.2021.108283. [PubMed:34731782 ]
Li T, Ren G, Jiang D, Liu C: Dynamic Changes in Endophytic Microorganisms and Metabolites During Natural Drying of Licorice. Front Microbiol. 2021 Oct 14;12:740721. doi: 10.3389/fmicb.2021.740721. eCollection 2021. [PubMed:34721339 ]
Chen J, Cheng XL, Li LF, Dai SY, Wang YD, Li MH, Guo XH, Wei F, Ma SC: A general procedure for establishing composite quality evaluation indices based on key quality attributes of traditional Chinese medicine. J Pharm Biomed Anal. 2022 Jan 5;207:114415. doi: 10.1016/j.jpba.2021.114415. Epub 2021 Oct 5. [PubMed:34655988 ]
Jiang D, Li P, Yin Y, Ren G, Liu C: Molecular cloning and functional characterization of UGTs from Glycyrrhiza uralensis flavonoid pathway. Int J Biol Macromol. 2021 Dec 1;192:1108-1116. doi: 10.1016/j.ijbiomac.2021.09.136. Epub 2021 Sep 25. [PubMed:34582913 ]

Showing NP-Card for Liquiritin (NP0044057)

MOL for NP0044057 (Liquiritin)

3D MOL for NP0044057 (Liquiritin)

3D SDF for NP0044057 (Liquiritin)

3D-SDF for NP0044057 (Liquiritin)

PDB for NP0044057 (Liquiritin)

3D PDB for NP0044057 (Liquiritin)

SMILES for NP0044057 (Liquiritin)

INCHI for NP0044057 (Liquiritin)

Structure for NP0044057 (Liquiritin)

3D Structure for NP0044057 (Liquiritin)