NP-MRD: Showing NP-Card for Isoglycyrol (NP0056804)

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Record Information

Version

2.0

Created at

2022-04-28 02:27:31 UTC

Updated at

2022-04-28 02:27:31 UTC

NP-MRD ID

NP0056804

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isoglycyrol

Description

Isoglycyrol belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan. Thus, isoglycyrol is considered to be a flavonoid. Isoglycyrol is found in Glycyrrhiza aspera, Glycyrrhiza glabra , Glycyrrhiza inflata , Glycyrrhiza sp. and Glycyrrhiza uralensis . Isoglycyrol was first documented in 2006 (PMID: 16441081). Based on a literature review a small amount of articles have been published on Isoglycyrol (PMID: 24479468) (PMID: 33365846) (PMID: 35029877) (PMID: 27210480).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282204272D          

 27 31  0  0  0  0            999 V2000
    4.8537   -1.2294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7719   -0.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0200   -0.0689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3500   -0.5502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4318   -1.3711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1837   -1.7107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7618   -1.8525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0099   -1.5129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3399   -1.9943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9281   -0.6920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5981   -0.2106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3473    0.5753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5223    0.5797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2632   -0.2035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4554   -0.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0934    0.2453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1657    1.0285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9736    1.1958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3830    1.6446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9381    0.7521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6081    1.2334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3600    0.8939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4419    0.0729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1504    1.9198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9213    1.9967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6056   -1.5689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2756   -1.0876    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 10 14  1  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
 13 18  1  0  0  0  0
 17 19  1  0  0  0  0
  3 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  2 23  1  0  0  0  0
 21 24  1  0  0  0  0
 21 25  1  0  0  0  0
  1 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END

     RDKit          3D

 45 49  0  0  0  0  0  0  0  0999 V2000
   -5.2446    1.6855    1.2681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1814    0.8849    1.7270 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9952    0.8752    1.0215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7871    1.6136   -0.1230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5735    1.5786   -0.8105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3696    2.2735   -1.8937 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2427    2.2753   -2.5804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0851    2.9586   -3.6193 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8272    1.5098   -2.1731 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0988    1.2771   -2.6246 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8286    1.7366   -3.7030 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1350    1.3188   -3.9208 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7269    0.4291   -3.0521 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0520   -0.0030   -3.2621 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9904   -0.0217   -1.9813 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6832    0.3833   -1.7456 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7864    0.1144   -0.8292 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6619    0.7553   -1.0311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5506    0.7859   -0.3370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7469    0.0423    0.8079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9467    0.0823    1.4796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0788   -0.7628    2.7113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4835   -2.1158    2.2967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0112   -1.9379    1.9770 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7139   -1.9753    3.3119 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5111   -3.0908    1.1496 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2696   -0.7481    1.2846 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1727    1.3553    1.8054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4078    1.6269    0.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0550    2.7316    1.5981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5825    2.2376   -0.5010 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3378    2.4391   -4.3751 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6969    1.6774   -4.7584 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4980   -0.6535   -2.6363 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4656   -0.7214   -1.3051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4437   -0.3624    3.5237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1240   -0.9255    2.9795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5887   -2.8613    3.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0156   -2.3894    1.3668 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1659   -2.6823    3.9606 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6681   -0.9788    3.7824 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7583   -2.3401    3.1721 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0582   -3.8303    1.7698 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1306   -2.6778    0.3338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3775   -3.5693    0.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 24 27  1  0
 27 20  1  0
 20 19  2  0
 19 18  1  0
 18  9  2  0
  9 10  1  0
 10 16  2  0
 16 17  1  0
 16 15  1  0
 15 13  2  0
 13 14  1  0
 13 12  1  0
 12 11  2  0
  9  7  1  0
  7  8  2  0
  7  6  1  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
 20 21  1  0
  5 19  1  0
 17 18  1  0
 11 10  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
 22 36  1  0
 22 37  1  0
 23 38  1  0
 23 39  1  0
 25 40  1  0
 25 41  1  0
 25 42  1  0
 26 43  1  0
 26 44  1  0
 26 45  1  0
 15 35  1  0
 14 34  1  0
 12 33  1  0
 11 32  1  0
  4 31  1  0
M  END


  Mrv1652304282204272D          

 27 31  0  0  0  0            999 V2000
    4.8537   -1.2294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7719   -0.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0200   -0.0689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3500   -0.5502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4318   -1.3711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1837   -1.7107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7618   -1.8525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0099   -1.5129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3399   -1.9943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9281   -0.6920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5981   -0.2106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3473    0.5753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5223    0.5797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2632   -0.2035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4554   -0.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0934    0.2453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1657    1.0285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9736    1.1958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3830    1.6446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9381    0.7521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6081    1.2334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3600    0.8939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4419    0.0729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1504    1.9198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9213    1.9967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6056   -1.5689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2756   -1.0876    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 10 14  1  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
 13 18  1  0  0  0  0
 17 19  1  0  0  0  0
  3 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  2 23  1  0  0  0  0
 21 24  1  0  0  0  0
 21 25  1  0  0  0  0
  1 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0056804

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2CCC(C)(C)OC2=C2C3=C(C4=C(O3)C=C(O)C=C4)C(=O)OC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H18O6/c1-21(2)7-6-12-13(24-3)9-15-17(18(12)27-21)19-16(20(23)26-15)11-5-4-10(22)8-14(11)25-19/h4-5,8-9,22H,6-7H2,1-3H3

> <INCHI_KEY>
OJFZQSUOBVJAIP-UHFFFAOYSA-N

> <FORMULA>
C21H18O6

> <MOLECULAR_WEIGHT>
366.369

> <EXACT_MASS>
366.1103383

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
38.45876289979886

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-hydroxy-15-methoxy-19,19-dimethyl-3,12,20-trioxapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{16,21}]henicosa-1(21),2(10),4(9),5,7,13,15-heptaen-11-one

> <ALOGPS_LOGP>
4.13

> <JCHEM_LOGP>
3.5671529769999997

> <ALOGPS_LOGS>
-3.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.103962450403502

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0632519646492122

> <JCHEM_POLAR_SURFACE_AREA>
78.13000000000001

> <JCHEM_REFRACTIVITY>
97.5326

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.87e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-hydroxy-15-methoxy-19,19-dimethyl-3,12,20-trioxapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{16,21}]henicosa-1(21),2(10),4(9),5,7,13,15-heptaen-11-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       9.060  -2.295   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.907  -0.762   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.504  -0.129   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.253  -1.027   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.406  -2.559   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.810  -3.193   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.155  -3.458   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.752  -2.824   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.501  -3.723   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.599  -1.292   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.850  -0.393   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.382   1.074   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.842   1.082   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.358  -0.380   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.850  -0.692   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.174   0.458   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.309   1.920   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.817   2.232   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.715   3.070   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       7.351   1.404   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       8.602   2.302   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.005   1.669   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.158   0.136   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.748   3.584   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.186   3.727   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      10.464  -2.929   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      11.714  -2.030   0.000  0.00  0.00           C+0
CONECT    1    2    6   26                                                  
CONECT    2    1    3   23                                                  
CONECT    3    2    4   20                                                  
CONECT    4    3    5   11                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   14                                                  
CONECT   11   10    4   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   10   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17   13                                                       
CONECT   19   17                                                            
CONECT   20    3   21                                                       
CONECT   21   20   22   24   25                                             
CONECT   22   21   23                                                       
CONECT   23   22    2                                                       
CONECT   24   21                                                            
CONECT   25   21                                                            
CONECT   26    1   27                                                       
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₁₈O₆

Average Mass

366.3690 Da

Monoisotopic Mass

366.11034 Da

IUPAC Name

6-hydroxy-15-methoxy-19,19-dimethyl-3,12,20-trioxapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{16,21}]henicosa-1(21),2(10),4(9),5,7,13,15-heptaen-11-one

Traditional Name

6-hydroxy-15-methoxy-19,19-dimethyl-3,12,20-trioxapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{16,21}]henicosa-1(21),2(10),4(9),5,7,13,15-heptaen-11-one

CAS Registry Number

Not Available

SMILES

COC1=C2CCC(C)(C)OC2=C2C3=C(C4=C(O3)C=C(O)C=C4)C(=O)OC2=C1

InChI Identifier

InChI=1S/C21H18O6/c1-21(2)7-6-12-13(24-3)9-15-17(18(12)27-21)19-16(20(23)26-15)11-5-4-10(22)8-14(11)25-19/h4-5,8-9,22H,6-7H2,1-3H3

InChI Key

OJFZQSUOBVJAIP-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 sp.	Plant	KNApSAcK
Glycyrrhiza uralensis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Coumestans

Direct Parent

Coumestans

Alternative Parents

Substituents

Coumestan
Angular pyranocoumarin
Pyranocoumarin
Angular furanocoumarin
Furanocoumarin
2,2-dimethyl-1-benzopyran
Coumarin
Chromane
Benzopyran
1-benzopyran
Benzofuran
Furopyran
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Furan
Lactone
Ether
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Coumestan flavonoids (LMPK12090045 )

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	4.13	ALOGPS
logP	3.57	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	9.1	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	78.13 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	97.53 m³·mol⁻¹	ChemAxon
Polarizability	38.46 Å³	ChemAxon
Number of Rings	5	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

C00009778

Chemspider ID

4477112

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5318570

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Villinski JR, Bergeron C, Cannistra JC, Gloer JB, Coleman CM, Ferreira D, Azelmat J, Grenier D, Gafner S: Pyrano-isoflavans from Glycyrrhiza uralensis with antibacterial activity against Streptococcus mutans and Porphyromonas gingivalis. J Nat Prod. 2014 Mar 28;77(3):521-6. doi: 10.1021/np400788r. Epub 2014 Jan 30. [PubMed:24479468 ]
He J, Chen L, Heber D, Shi W, Lu QY: Antibacterial compounds from Glycyrrhiza uralensis. J Nat Prod. 2006 Jan;69(1):121-4. doi: 10.1021/np058069d. [PubMed:16441081 ]
Jia G, Li P, Zhu Q, Peng L: Characterization of the complete chloroplast genome of Glycyrrhiza uralensis (Leguminosae), a traditional Chinese medicine. Mitochondrial DNA B Resour. 2019 Sep 18;4(2):3040-3041. doi: 10.1080/23802359.2019.1666050. [PubMed:33365846 ]
Simayi J, Nuermaimaiti M, Wumaier A, Khan N, Yusufu M, Nuer M, Maihemuti N, Bayinsang, Adurusul K, Zhou W: Analysis of the active components and mechanism of Shufeng Jiedu capsule against COVID-19 based on network pharmacology and molecular docking. Medicine (Baltimore). 2022 Jan 7;101(1):e28286. doi: 10.1097/MD.0000000000028286. [PubMed:35029877 ]
Shults EE, Shakirov MM, Pokrovsky MA, Petrova TN, Pokrovsky AG, Gorovoy PG: Phenolic compounds from Glycyrrhiza pallidiflora Maxim. and their cytotoxic activity. Nat Prod Res. 2017 Feb;31(4):445-452. doi: 10.1080/14786419.2016.1188094. Epub 2016 May 22. [PubMed:27210480 ]

Showing NP-Card for Isoglycyrol (NP0056804)

MOL for NP0056804 (Isoglycyrol)

3D MOL for NP0056804 (Isoglycyrol)

3D SDF for NP0056804 (Isoglycyrol)

3D-SDF for NP0056804 (Isoglycyrol)

PDB for NP0056804 (Isoglycyrol)

3D PDB for NP0056804 (Isoglycyrol)

SMILES for NP0056804 (Isoglycyrol)

INCHI for NP0056804 (Isoglycyrol)

Structure for NP0056804 (Isoglycyrol)

3D Structure for NP0056804 (Isoglycyrol)