NP-MRD: Showing NP-Card for Glycycoumarin (NP0057037)

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Record Information

Version

2.0

Created at

2022-04-28 02:36:19 UTC

Updated at

2022-04-28 02:36:19 UTC

NP-MRD ID

NP0057037

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Glycycoumarin

Description

Glycycoumarin belongs to the class of organic compounds known as hydroxyisoflavonoids. These are organic compounds containing an isoflavonoid skeleton carrying one or more hydroxyl groups. Thus, glycycoumarin is considered to be a flavonoid lipid molecule. Glycycoumarin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Glycycoumarin has been detected, but not quantified in, root vegetables. Glycycoumarin is found in Glycyrrhiza aspera, Glycyrrhiza glabra , Glycyrrhiza inflata and Glycyrrhiza uralensis . Glycycoumarin was first documented in 2003 (PMID: 12808302). This could make glycycoumarin a potential biomarker for the consumption of these foods (PMID: 20724155) (PMID: 16387459) (PMID: 23164761).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061310182D          

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

     RDKit          3D

 47 49  0  0  0  0  0  0  0  0999 V2000
   -0.6226   -0.0788   -2.7280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8420   -0.4873   -1.3930 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8371    0.4004   -0.3254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0239    0.9975    0.0410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2859    0.7170   -0.6758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8109   -0.6152   -0.3029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0039   -0.7587    0.2040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5183   -2.1215    0.5772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8740    0.4173    0.4112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0172    1.8735    1.0947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1623    2.5035    1.5119 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8384    2.1456    1.7699 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3372    1.5285    1.3762 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4675    1.7735    2.0042 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6043    1.2139    1.6675 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6267    1.5139    2.3295 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7068    0.3199    0.6239 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9458   -0.3220    0.2180 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8024   -0.8841    1.1420 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9780   -1.4915    0.7519 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3604   -1.5707   -0.5714 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5374   -2.1760   -0.9901 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5070   -1.0095   -1.5036 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3333   -0.4034   -1.1127 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4733    0.1615   -2.0450 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5291    0.0534   -0.0437 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3491    0.6506    0.3256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9709    0.9631   -2.8815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2166   -0.7248   -3.3925 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4344   -0.1247   -3.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0518    1.4802   -0.3822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1082    0.7643   -1.7790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1861   -1.5056   -0.4546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1627   -2.0654    1.4610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6468   -2.7684    0.8158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0089   -2.5817   -0.3106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4653    1.0970    1.1580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8754    0.0886    0.7981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9915    0.9343   -0.5717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1722    3.1506    2.2869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8176    2.8354    2.6044 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5016   -0.8228    2.1937 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6273   -1.9219    1.4989 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3886   -1.5954   -1.0594 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8094   -1.0719   -2.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6453    0.1655   -3.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5458   -0.6478   -0.8806 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  3
  7  8  1  0
  7  9  1  0
  4 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 27  2  0
 27 26  1  0
 26 17  2  0
 17 15  1  0
 15 16  2  0
 15 14  1  0
 17 18  1  0
 18 24  2  0
 24 25  1  0
 24 23  1  0
 23 21  2  0
 21 22  1  0
 21 20  1  0
 20 19  2  0
 27  3  1  0
 19 18  1  0
 14 13  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  8 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
  9 39  1  0
 11 40  1  0
 12 41  1  0
 26 47  1  0
 25 46  1  0
 23 45  1  0
 22 44  1  0
 20 43  1  0
 19 42  1  0
M  END


  Mrv0541 05061310182D          

 27 29  0  0  0  0            999 V2000
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    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
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   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
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    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
   -3.5724    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
 11  1  1  0  0  0  0
 11  2  1  0  0  0  0
 11  4  2  0  0  0  0
 12  5  1  0  0  0  0
 12  8  2  0  0  0  0
 13  7  1  0  0  0  0
 14  6  1  0  0  0  0
 15  9  2  0  0  0  0
 15 13  1  0  0  0  0
 16  9  1  0  0  0  0
 17  8  1  0  0  0  0
 17 13  2  0  0  0  0
 18 10  2  0  0  0  0
 18 14  1  0  0  0  0
 19 10  1  0  0  0  0
 19 16  2  0  0  0  0
 20 14  2  0  0  0  0
 20 16  1  0  0  0  0
 21 15  1  0  0  0  0
 22 12  1  0  0  0  0
 23 17  1  0  0  0  0
 24 18  1  0  0  0  0
 25 21  2  0  0  0  0
 26  3  1  0  0  0  0
 26 20  1  0  0  0  0
 27 19  1  0  0  0  0
 27 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0057037

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(CC=C(C)C)C(O)=CC2=C1C=C(C(=O)O2)C1=C(O)C=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O6/c1-11(2)4-6-14-18(24)10-19-16(20(14)26-3)9-15(21(25)27-19)13-7-5-12(22)8-17(13)23/h4-5,7-10,22-24H,6H2,1-3H3

> <INCHI_KEY>
NZYSZZDSYIBYLC-UHFFFAOYSA-N

> <FORMULA>
C21H20O6

> <MOLECULAR_WEIGHT>
368.3799

> <EXACT_MASS>
368.125988372

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
39.007957752170114

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(2,4-dihydroxyphenyl)-7-hydroxy-5-methoxy-6-(3-methylbut-2-en-1-yl)-2H-chromen-2-one

> <ALOGPS_LOGP>
4.06

> <JCHEM_LOGP>
4.111647179333334

> <ALOGPS_LOGS>
-4.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.554700103996533

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.601662780880913

> <JCHEM_PKA_STRONGEST_BASIC>
-4.873010248114108

> <JCHEM_POLAR_SURFACE_AREA>
96.22

> <JCHEM_REFRACTIVITY>
102.64939999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.44e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
glycycoumarin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -6.668   6.930   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   11                                                            
CONECT    3   26                                                            
CONECT    4    6   11                                                       
CONECT    5    7   12                                                       
CONECT    6    4   14                                                       
CONECT    7    5   13                                                       
CONECT    8   12   17                                                       
CONECT    9   15   16                                                       
CONECT   10   18   19                                                       
CONECT   11    1    2    4                                                  
CONECT   12    5    8   22                                                  
CONECT   13    7   15   17                                                  
CONECT   14    6   18   20                                                  
CONECT   15    9   13   21                                                  
CONECT   16    9   19   20                                                  
CONECT   17    8   13   23                                                  
CONECT   18   10   14   24                                                  
CONECT   19   10   16   27                                                  
CONECT   20   14   16   26                                                  
CONECT   21   15   25   27                                                  
CONECT   22   12                                                            
CONECT   23   17                                                            
CONECT   24   18                                                            
CONECT   25   21                                                            
CONECT   26    3   20                                                       
CONECT   27   19   21                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

View in JSmol

Synonyms

Value	Source
3-(2,4-Dihydroxy-phenyl)-7-hydroxy-5-methoxy-6-(3-methyl-but-2-enyl)-1-benzopyran-2-one	ChEBI
3-(2,4-Dihydroxyphenyl)-7-hydroxy-5-methoxy-6-(3-methyl-2-butenyl)-2H-1-benzopyran-2-one, 9ci	HMDB

Chemical Formula

C₂₁H₂₀O₆

Average Mass

368.3799 Da

Monoisotopic Mass

368.12599 Da

IUPAC Name

3-(2,4-dihydroxyphenyl)-7-hydroxy-5-methoxy-6-(3-methylbut-2-en-1-yl)-2H-chromen-2-one

Traditional Name

glycycoumarin

CAS Registry Number

Not Available

SMILES

COC1=C(CC=C(C)C)C(O)=CC2=C1C=C(C(=O)O2)C1=C(O)C=C(O)C=C1

InChI Identifier

InChI=1S/C21H20O6/c1-11(2)4-6-14-18(24)10-19-16(20(14)26-3)9-15(21(25)27-19)13-7-5-12(22)8-17(13)23/h4-5,7-10,22-24H,6H2,1-3H3

InChI Key

NZYSZZDSYIBYLC-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Glycyrrhiza aspera	Plant	KNApSAcK
Glycyrrhiza glabra	Plant	KNApSAcK
Glycyrrhiza inflata	Plant	KNApSAcK
Glycyrrhiza uralensis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxyisoflavonoids. These are organic compounds containing an isoflavonoid skeleton carrying one or more hydroxyl groups.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Hydroxyisoflavonoids

Direct Parent

Hydroxyisoflavonoids

Alternative Parents

Substituents

Hydroxyisoflavonoid
Isoflav-3-enone skeleton
7-hydroxycoumarin
Hydroxycoumarin
Coumarin
Benzopyran
1-benzopyran
Anisole
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Monocyclic benzene moiety
Pyran
Benzenoid
Heteroaromatic compound
Lactone
Ether
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aromatic ether (CHEBI:69087 )
resorcinols (CHEBI:69087 )
coumarins (CHEBI:69087 )
Other Flavonoids (LMPK12160018 )

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	4.06	ALOGPS
logP	4.11	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	7.6	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	102.65 m³·mol⁻¹	ChemAxon
Polarizability	39.01 Å³	ChemAxon
Number of Rings	3	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

HMDB0038225

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB017468

KNApSAcK ID

C00010040

Chemspider ID

4476511

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5317756

PDB ID

Not Available

ChEBI ID

69087

Good Scents ID

Not Available

References

General References

Li S, Li W, Wang Y, Asada Y, Koike K: Prenylflavonoids from Glycyrrhiza uralensis and their protein tyrosine phosphatase-1B inhibitory activities. Bioorg Med Chem Lett. 2010 Sep 15;20(18):5398-401. doi: 10.1016/j.bmcl.2010.07.110. Epub 2010 Aug 1. [PubMed:20724155 ]
Hayashi H, Hattori S, Inoue K, Sarsenbaev K, Ito M, Honda G: Field survey of Glycyrrhiza plants in Central Asia (1). Characterization of G. uralensis, G. glabra and the putative intermediate collected in Kazakhstan. Biol Pharm Bull. 2003 Jun;26(6):867-71. doi: 10.1248/bpb.26.867. [PubMed:12808302 ]
Sato Y, Akao T, He JX, Nojima H, Kuraishi Y, Morota T, Asano T, Tani T: Glycycoumarin from Glycyrrhizae Radix acts as a potent antispasmodic through inhibition of phosphodiesterase 3. J Ethnopharmacol. 2006 May 24;105(3):409-14. doi: 10.1016/j.jep.2005.11.017. Epub 2006 Jan 4. [PubMed:16387459 ]
Lee KK, Omiya Y, Yuzurihara M, Kase Y, Kobayashi H: Antispasmodic effect of shakuyakukanzoto extract on experimental muscle cramps in vivo: role of the active constituents of Glycyrrhizae radix. J Ethnopharmacol. 2013 Jan 9;145(1):286-93. doi: 10.1016/j.jep.2012.11.005. Epub 2012 Nov 17. [PubMed:23164761 ]

Showing NP-Card for Glycycoumarin (NP0057037)

MOL for NP0057037 (Glycycoumarin)

3D MOL for NP0057037 (Glycycoumarin)

3D SDF for NP0057037 (Glycycoumarin)

3D-SDF for NP0057037 (Glycycoumarin)

PDB for NP0057037 (Glycycoumarin)

3D PDB for NP0057037 (Glycycoumarin)

SMILES for NP0057037 (Glycycoumarin)

INCHI for NP0057037 (Glycycoumarin)

Structure for NP0057037 (Glycycoumarin)

3D Structure for NP0057037 (Glycycoumarin)