NP-MRD: Showing NP-Card for Isoliquiritin (NP0044056)

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Record Information

Version

1.0

Created at

2021-11-12 23:47:35 UTC

Updated at

2021-11-26 17:44:56 UTC

NP-MRD ID

NP0044056

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isoliquiritin

Description

Isoliquiritin 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. Thus, isoliquiritin is considered to be a flavonoid. Isoliquiritin 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. Isoliquiritin is found in Allium chinense , Glycyrrhiza aspera, Glycyrrhiza glabra , Glycyrrhiza inflata , Glycyrrhiza kansuensis, Glycyrrhiza spp., Glycyrrhiza spp.,, Glycyrrhiza uralensis and Trifolium subterraneum . It was first documented in 2005 (PMID: 16159166). Based on a literature review a small amount of articles have been published on isoliquiritin (PMID: 23325115) (PMID: 23336517) (PMID: 24247527) (PMID: 25871879).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652311132100472D          

 30 32  0  0  1  0            999 V2000
    5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  1  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
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  5  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  1  0  0  0
  1 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 21 28  1  0  0  0  0
 16 29  1  0  0  0  0
 29 30  2  0  0  0  0
 13 30  1  0  0  0  0
M  END

     RDKit          3D

 52 54  0  0  0  0  0  0  0  0999 V2000
    5.2721   -2.5189   -1.6273 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9502   -1.4412   -0.9302 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5627   -1.2764   -0.8389 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8382   -0.3674   -0.2561 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3507   -0.3629   -0.2702 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7172    0.6703    0.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6591    0.7451    0.4268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4673   -0.1874   -0.1884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8247   -0.1279   -0.1654 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6194    0.8300    0.4477 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2990    0.1843    1.4734 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4143   -0.4902    1.0582 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1781   -1.4973   -0.0241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4243   -2.0886   -0.3226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4644    0.5256    0.7352 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.7478    1.2075    1.9410 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9671    1.4866   -0.2830 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.6333    1.1742   -1.4955 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5133    1.5713   -0.4966 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1558    2.9316   -0.5765 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8160   -1.2367   -0.8629 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5755   -1.2830   -0.8771 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0983   -0.7316   -0.4555 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0688    0.4165    0.2910 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2160    1.0810    0.7364 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4481    0.5912    0.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5751    1.2556    0.8771 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5400   -0.5384   -0.3019 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4002   -1.2209   -0.7590 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5790   -2.3284   -1.4774 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9074   -2.0676   -1.3608 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3383    0.4195    0.2612 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2886    1.4278    0.8928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0546    1.5982    0.9767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9813    1.5798    0.9427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7823   -1.0739    1.9532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5097   -2.2715    0.3567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7963   -1.0979   -0.9607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9835   -2.1261    0.4891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4263    0.0613    0.4313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2424    2.0555    1.9973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4061    2.4949   -0.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5996    1.0954   -1.2322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2727    1.1724   -1.5283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2015    3.0107   -0.3330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4201   -1.9789   -1.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0201   -2.1158   -1.4132 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1407    0.8788    0.5813 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1238    1.9723    1.3152 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0285    1.9886    0.3296 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5138   -0.9337   -0.5480 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3072   -3.0634   -1.9587 H   0  0  0  0  0  0  0  0  0  0  0  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
  9  8  1  0
  8  7  2  0
  7  6  1  0
  6  5  2  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  2  0
  2 23  1  0
 23 29  2  0
 29 30  1  0
 29 28  1  0
 28 26  2  0
 26 27  1  0
 26 25  1  0
 25 24  2  0
  5 22  1  0
 22 21  2  0
 19 10  1  0
 21  8  1  0
 24 23  1  0
 10 35  1  1
 12 36  1  1
 13 37  1  0
 13 38  1  0
 14 39  1  0
 15 40  1  6
 16 41  1  0
 17 42  1  1
 18 43  1  0
 19 44  1  6
 20 45  1  0
  7 34  1  0
  6 33  1  0
  4 32  1  0
  3 31  1  0
 30 52  1  0
 28 51  1  0
 27 50  1  0
 25 49  1  0
 24 48  1  0
 22 47  1  0
 21 46  1  0
M  END


  Mrv1652311132100472D          

 30 32  0  0  1  0            999 V2000
    5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  1  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
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  5  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  1  0  0  0
  1 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 21 28  1  0  0  0  0
 16 29  1  0  0  0  0
 29 30  2  0  0  0  0
 13 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0044056

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H22O9/c22-10-17-18(26)19(27)20(28)21(30-17)29-13-5-1-11(2-6-13)3-8-15(24)14-7-4-12(23)9-16(14)25/h1-9,17-23,25-28H,10H2/b8-3+/t17-,18-,19+,20-,21-/m1/s1

> <INCHI_KEY>
YNWXJFQOCHMPCK-LXGDFETPSA-N

> <FORMULA>
C21H22O9

> <MOLECULAR_WEIGHT>
418.398

> <EXACT_MASS>
418.126382288

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
42.21171847640438

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-1-(2,4-dihydroxyphenyl)-3-(4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-en-1-one

> <ALOGPS_LOGP>
0.82

> <JCHEM_LOGP>
1.361561250666667

> <ALOGPS_LOGS>
-2.89

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.749587052338391

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.116176143173165

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092343686506

> <JCHEM_POLAR_SURFACE_AREA>
156.91

> <JCHEM_REFRACTIVITY>
104.96409999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.36e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isoliquiritin

> <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      10.669  -3.080   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      13.337  -9.240   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      10.669  -9.240   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.337   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.670  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      16.004   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.338  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      18.672  -0.000   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      18.672   1.540   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      20.005  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      21.339  -0.000   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      21.339   1.540   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      22.673  -0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      22.673  -2.310   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      24.006  -3.080   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      21.339  -3.080   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      20.005  -2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.670  -2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2   13                                                       
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5                                                            
CONECT    7    4    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    2   12                                                  
CONECT   12   11                                                            
CONECT   13    1   14   30                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   29                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   28                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   21                                                       
CONECT   29   16   30                                                       
CONECT   30   29   13                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Value	Source
4-beta-D-Glucopyranosyloxy-2',4'-dihydroxy-trans-chalcone	ChEBI
4-b-D-Glucopyranosyloxy-2',4'-dihydroxy-trans-chalcone	Generator
4-Β-D-glucopyranosyloxy-2',4'-dihydroxy-trans-chalcone	Generator
4-((1E)-3-(2,4-Dihydroxyphenyl)-3-oxo-1-propen-1-yl)phenyl beta-D-glucopyranoside	MeSH
Neoisoliquiritin	MeSH
Neoisoliquiritin, (e)-isomer	MeSH

Chemical Formula

C₂₁H₂₂O₉

Average Mass

418.3980 Da

Monoisotopic Mass

418.12638 Da

IUPAC Name

(2E)-1-(2,4-dihydroxyphenyl)-3-(4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-en-1-one

Traditional Name

isoliquiritin

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C21H22O9/c22-10-17-18(26)19(27)20(28)21(30-17)29-13-5-1-11(2-6-13)3-8-15(24)14-7-4-12(23)9-16(14)25/h1-9,17-23,25-28H,10H2/b8-3+/t17-,18-,19+,20-,21-/m1/s1

InChI Key

YNWXJFQOCHMPCK-LXGDFETPSA-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
Allium chinense	Plant	KNApSAcK
Glycyrrhiza aspera	Plant	KNApSAcK
Glycyrrhiza glabra	Plant	KNApSAcK
Glycyrrhiza inflata	Plant	KNApSAcK
Glycyrrhiza kansuensis	Plant	KNApSAcK
Glycyrrhiza spp.	Plant	KNApSAcK
Glycyrrhiza spp.,	Plant	KNApSAcK
Glycyrrhiza uralensis	Plant	KNApSAcK
Trifolium subterraneum	Plant	KNApSAcK

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 o-glycoside
2'-hydroxychalcone
Linear 1,3-diarylpropanoid
Phenolic glycoside
Cinnamylphenol
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Benzoyl
Phenoxy compound
Phenol ether
Resorcinol
Styrene
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monosaccharide
Oxane
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Enone
Acryloyl-group
Alpha,beta-unsaturated ketone
Ketone
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Polyol
Acetal
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Alcohol
Primary alcohol
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

beta-D-glucoside (CHEBI:80839 )
monosaccharide derivative (CHEBI:80839 )
resorcinols (CHEBI:80839 )
chalcones (CHEBI:80839 )
Chalcones and dihydrochalcones (C16978 )
Chalcones and dihydrochalcones (LMPK12120021 )

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	0.82	ALOGPS
logP	1.36	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	7.12	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	156.91 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	104.96 m³·mol⁻¹	ChemAxon
Polarizability	42.21 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00007184

Chemspider ID

4477128

KEGG Compound ID

C16978

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5318591

PDB ID

Not Available

ChEBI ID

80839

Good Scents ID

rw1859791

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 ]
Dirican E, Turkez H: In vitro studies on protective effect of Glycyrrhiza glabra root extracts against cadmium-induced genetic and oxidative damage in human lymphocytes. Cytotechnology. 2014 Jan;66(1):9-16. doi: 10.1007/s10616-012-9531-5. Epub 2013 Jan 17. [PubMed:23325115 ]
Wu YP, Meng XS, Bao YR, Wang S, Kang TG: Simultaneous quantitative determination of nine active chemical compositions in traditional Chinese medicine Glycyrrhiza by RP-HPLC with full-time five-wavelength fusion method. Am J Chin Med. 2013;41(1):211-9. doi: 10.1142/S0192415X13500158. [PubMed:23336517 ]
Zhou Y, Ho WS: Combination of liquiritin, isoliquiritin and isoliquirigenin induce apoptotic cell death through upregulating p53 and p21 in the A549 non-small cell lung cancer cells. Oncol Rep. 2014 Jan;31(1):298-304. doi: 10.3892/or.2013.2849. Epub 2013 Nov 14. [PubMed:24247527 ]
Wang R, Zhang CY, Bai LP, Pan HD, Shu LM, Kong AN, Leung EL, Liu L, Li T: Flavonoids derived from liquorice suppress murine macrophage activation by up-regulating heme oxygenase-1 independent of Nrf2 activation. Int Immunopharmacol. 2015 Oct;28(2):917-24. doi: 10.1016/j.intimp.2015.03.040. Epub 2015 Apr 11. [PubMed:25871879 ]

Showing NP-Card for Isoliquiritin (NP0044056)

MOL for NP0044056 (Isoliquiritin)

3D MOL for NP0044056 (Isoliquiritin)

3D SDF for NP0044056 (Isoliquiritin)

3D-SDF for NP0044056 (Isoliquiritin)

PDB for NP0044056 (Isoliquiritin)

3D PDB for NP0044056 (Isoliquiritin)

SMILES for NP0044056 (Isoliquiritin)

INCHI for NP0044056 (Isoliquiritin)

Structure for NP0044056 (Isoliquiritin)

3D Structure for NP0044056 (Isoliquiritin)