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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:37:59 UTC

Update Date

2022-03-07 02:53:53 UTC

HMDB ID

HMDB0033859

Secondary Accession Numbers

HMDB33859

Metabolite Identification

Common Name

Glyzaglabrin

Description

Glyzaglabrin belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom. Thus, glyzaglabrin is considered to be a flavonoid. Glyzaglabrin has been detected, but not quantified in, several different foods, such as herbal tea, red tea, green tea, teas (Camellia sinensis), and black tea. This could make glyzaglabrin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Glyzaglabrin.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0033859
     RDKit          3D
Glyzaglabrin
 32 35  0  0  0  0  0  0  0  0999 V2000
    0.4403    0.6082    1.5162 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9259    0.0810    0.4894 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1219   -0.5508   -0.4284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3015   -0.6195   -0.2147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9861   -1.7924    0.0252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3471   -1.8158    0.2302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0718   -0.6444    0.1999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4234    0.5583   -0.0381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0759    0.5469   -0.2371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3811    1.7258   -0.4787 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4168    1.5370   -0.0049 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5184    0.9996    0.7418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4433   -0.3819    0.3736 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6916   -1.1114   -1.5343 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0133   -1.0418   -1.7110 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8149   -0.4493   -0.8598 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1867   -0.3897   -1.0657 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0077    0.2390   -0.1558 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3785    0.3066   -0.3477 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4583    0.8143    0.9707 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1076    0.7578    1.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3097    0.1316    0.2657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3906   -2.7066    0.0436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8412   -2.7517    0.4138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9080    2.5807   -0.5009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2490    1.0866    1.8122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4659    1.4654    0.4692 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1288   -1.6327   -2.3148 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5942   -0.8473   -1.9555 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9708    0.7700    0.3272 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0509    1.3277    1.7334 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6191    1.1990    2.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
  3 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 22  2  1  0
  9  4  1  0
 22 16  1  0
 13  7  1  0
  5 23  1  0
  6 24  1  0
 10 25  1  0
 12 26  1  0
 12 27  1  0
 14 28  1  0
 17 29  1  0
 19 30  1  0
 20 31  1  0
 21 32  1  0
M  END


  Mrv0541 05061307242D          

 22 25  0  0  0  0            999 V2000
    5.4957   -6.4729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -6.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -5.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -6.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -5.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246   -6.4729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -5.2354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -3.9979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -2.5055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -3.8404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  4  3  2  0  0  0  0
  8  1  1  0  0  0  0
  8  5  2  0  0  0  0
  9  3  1  0  0  0  0
 10  2  1  0  0  0  0
 11  6  2  0  0  0  0
 11  9  1  0  0  0  0
 12  4  1  0  0  0  0
 13  5  1  0  0  0  0
 13 10  2  0  0  0  0
 14 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15  9  2  0  0  0  0
 16 12  2  0  0  0  0
 16 15  1  0  0  0  0
 17  8  1  0  0  0  0
 18 14  2  0  0  0  0
 19 15  1  0  0  0  0
 20  6  1  0  0  0  0
 20 13  1  0  0  0  0
 21  7  1  0  0  0  0
 21 12  1  0  0  0  0
 22  7  1  0  0  0  0
 22 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033859

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC2=C(C=C1)C(=O)C(=CO2)C1=C(O)C2=C(OCO2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H10O6/c17-8-1-2-10-13(5-8)20-6-11(14(10)18)9-3-4-12-16(15(9)19)22-7-21-12/h1-6,17,19H,7H2

> <INCHI_KEY>
GRMSSCUVELGNHC-UHFFFAOYSA-N

> <FORMULA>
C16H10O6

> <MOLECULAR_WEIGHT>
298.247

> <EXACT_MASS>
298.047738052

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
29.016520962719746

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-hydroxy-3-(4-hydroxy-2H-1,3-benzodioxol-5-yl)-4H-chromen-4-one

> <ALOGPS_LOGP>
2.71

> <JCHEM_LOGP>
2.353671179

> <ALOGPS_LOGS>
-3.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.011857509155961

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.471456463148671

> <JCHEM_PKA_STRONGEST_BASIC>
-4.676357670603118

> <JCHEM_POLAR_SURFACE_AREA>
85.22000000000001

> <JCHEM_REFRACTIVITY>
75.4689

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.58e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
glyzaglabrin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033859
     RDKit          3D
Glyzaglabrin
 32 35  0  0  0  0  0  0  0  0999 V2000
    0.4403    0.6082    1.5162 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9259    0.0810    0.4894 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1219   -0.5508   -0.4284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3015   -0.6195   -0.2147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9861   -1.7924    0.0252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3471   -1.8158    0.2302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0718   -0.6444    0.1999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4234    0.5583   -0.0381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0759    0.5469   -0.2371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3811    1.7258   -0.4787 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4168    1.5370   -0.0049 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5184    0.9996    0.7418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4433   -0.3819    0.3736 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6916   -1.1114   -1.5343 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0133   -1.0418   -1.7110 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8149   -0.4493   -0.8598 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1867   -0.3897   -1.0657 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0077    0.2390   -0.1558 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3785    0.3066   -0.3477 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4583    0.8143    0.9707 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1076    0.7578    1.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3097    0.1316    0.2657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3906   -2.7066    0.0436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8412   -2.7517    0.4138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9080    2.5807   -0.5009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2490    1.0866    1.8122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4659    1.4654    0.4692 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1288   -1.6327   -2.3148 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5942   -0.8473   -1.9555 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9708    0.7700    0.3272 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0509    1.3277    1.7334 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6191    1.1990    2.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
  3 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 22  2  1  0
  9  4  1  0
 22 16  1  0
 13  7  1  0
  5 23  1  0
  6 24  1  0
 10 25  1  0
 12 26  1  0
 12 27  1  0
 14 28  1  0
 17 29  1  0
 19 30  1  0
 20 31  1  0
 21 32  1  0
M  END

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      10.259 -12.083   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.925 -11.313   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.258  -5.153   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.924  -4.383   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.592  -9.773   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.925  -6.693   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.220  -5.923   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.592 -11.313   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.258  -6.693   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.925  -9.773   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.591  -7.463   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.590  -5.153   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.259  -9.003   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.591  -9.003   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.924  -7.463   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.590  -6.693   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      12.926 -12.083   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.258  -9.773   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.924  -9.003   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      10.259  -7.463   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.126  -4.677   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.126  -7.169   0.000  0.00  0.00           O+0
CONECT    1    2    8                                                       
CONECT    2    1   10                                                       
CONECT    3    4    9                                                       
CONECT    4    3   12                                                       
CONECT    5    8   13                                                       
CONECT    6   11   20                                                       
CONECT    7   21   22                                                       
CONECT    8    1    5   17                                                  
CONECT    9    3   11   15                                                  
CONECT   10    2   13   14                                                  
CONECT   11    6    9   14                                                  
CONECT   12    4   16   21                                                  
CONECT   13    5   10   20                                                  
CONECT   14   10   11   18                                                  
CONECT   15    9   16   19                                                  
CONECT   16   12   15   22                                                  
CONECT   17    8                                                            
CONECT   18   14                                                            
CONECT   19   15                                                            
CONECT   20    6   13                                                       
CONECT   21    7   12                                                       
CONECT   22    7   16                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0033859
HETATM    1  O1  UNL     1       0.440   0.608   1.516  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.926   0.081   0.489  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.122  -0.551  -0.428  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.302  -0.620  -0.215  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.986  -1.792   0.025  1.00  0.00           C  
HETATM    6  C5  UNL     1      -3.347  -1.816   0.230  1.00  0.00           C  
HETATM    7  C6  UNL     1      -4.072  -0.644   0.200  1.00  0.00           C  
HETATM    8  C7  UNL     1      -3.423   0.558  -0.038  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.076   0.547  -0.237  1.00  0.00           C  
HETATM   10  O2  UNL     1      -1.381   1.726  -0.479  1.00  0.00           O  
HETATM   11  O3  UNL     1      -4.417   1.537  -0.005  1.00  0.00           O  
HETATM   12  C9  UNL     1      -5.518   1.000   0.742  1.00  0.00           C  
HETATM   13  O4  UNL     1      -5.443  -0.382   0.374  1.00  0.00           O  
HETATM   14  C10 UNL     1       0.692  -1.111  -1.534  1.00  0.00           C  
HETATM   15  O5  UNL     1       2.013  -1.042  -1.711  1.00  0.00           O  
HETATM   16  C11 UNL     1       2.815  -0.449  -0.860  1.00  0.00           C  
HETATM   17  C12 UNL     1       4.187  -0.390  -1.066  1.00  0.00           C  
HETATM   18  C13 UNL     1       5.008   0.239  -0.156  1.00  0.00           C  
HETATM   19  O6  UNL     1       6.379   0.307  -0.348  1.00  0.00           O  
HETATM   20  C14 UNL     1       4.458   0.814   0.971  1.00  0.00           C  
HETATM   21  C15 UNL     1       3.108   0.758   1.177  1.00  0.00           C  
HETATM   22  C16 UNL     1       2.310   0.132   0.266  1.00  0.00           C  
HETATM   23  H1  UNL     1      -1.391  -2.707   0.044  1.00  0.00           H  
HETATM   24  H2  UNL     1      -3.841  -2.752   0.414  1.00  0.00           H  
HETATM   25  H3  UNL     1      -1.908   2.581  -0.501  1.00  0.00           H  
HETATM   26  H4  UNL     1      -5.249   1.087   1.812  1.00  0.00           H  
HETATM   27  H5  UNL     1      -6.466   1.465   0.469  1.00  0.00           H  
HETATM   28  H6  UNL     1       0.129  -1.633  -2.315  1.00  0.00           H  
HETATM   29  H7  UNL     1       4.594  -0.847  -1.956  1.00  0.00           H  
HETATM   30  H8  UNL     1       6.971   0.770   0.327  1.00  0.00           H  
HETATM   31  H9  UNL     1       5.051   1.328   1.733  1.00  0.00           H  
HETATM   32  H10 UNL     1       2.619   1.199   2.055  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   22
CONECT    3    4   14   14
CONECT    4    5    5    9
CONECT    5    6   23
CONECT    6    7    7   24
CONECT    7    8   13
CONECT    8    9    9   11
CONECT    9   10
CONECT   10   25
CONECT   11   12
CONECT   12   13   26   27
CONECT   14   15   28
CONECT   15   16
CONECT   16   17   17   22
CONECT   17   18   29
CONECT   18   19   20   20
CONECT   19   30
CONECT   20   21   31
CONECT   21   22   22   32
END

HMDB0033859
     RDKit          3D
Glyzaglabrin
 32 35  0  0  0  0  0  0  0  0999 V2000
    0.4403    0.6082    1.5162 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9259    0.0810    0.4894 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1219   -0.5508   -0.4284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3015   -0.6195   -0.2147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9861   -1.7924    0.0252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3471   -1.8158    0.2302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0718   -0.6444    0.1999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4234    0.5583   -0.0381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0759    0.5469   -0.2371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3811    1.7258   -0.4787 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4168    1.5370   -0.0049 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5184    0.9996    0.7418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4433   -0.3819    0.3736 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6916   -1.1114   -1.5343 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0133   -1.0418   -1.7110 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8149   -0.4493   -0.8598 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1867   -0.3897   -1.0657 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0077    0.2390   -0.1558 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3785    0.3066   -0.3477 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4583    0.8143    0.9707 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1076    0.7578    1.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3097    0.1316    0.2657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3906   -2.7066    0.0436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8412   -2.7517    0.4138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9080    2.5807   -0.5009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2490    1.0866    1.8122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4659    1.4654    0.4692 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1288   -1.6327   -2.3148 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5942   -0.8473   -1.9555 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9708    0.7700    0.3272 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0509    1.3277    1.7334 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6191    1.1990    2.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
  3 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 22  2  1  0
  9  4  1  0
 22 16  1  0
 13  7  1  0
  5 23  1  0
  6 24  1  0
 10 25  1  0
 12 26  1  0
 12 27  1  0
 14 28  1  0
 17 29  1  0
 19 30  1  0
 20 31  1  0
 21 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2',7-Dihydroxy-3',4'-methylenedioxyisoflavone	HMDB
7,2'-Dihydroxy-3',4'-methylenedioxyisoflavone	HMDB

Chemical Formula

C₁₆H₁₀O₆

Average Molecular Weight

298.247

Monoisotopic Molecular Weight

298.047738052

IUPAC Name

7-hydroxy-3-(4-hydroxy-2H-1,3-benzodioxol-5-yl)-4H-chromen-4-one

Traditional Name

glyzaglabrin

CAS Registry Number

65242-64-0

SMILES

OC1=CC2=C(C=C1)C(=O)C(=CO2)C1=C(O)C2=C(OCO2)C=C1

InChI Identifier

InChI=1S/C16H10O6/c17-8-1-2-10-13(5-8)20-6-11(14(10)18)9-3-4-12-16(15(9)19)22-7-21-12/h1-6,17,19H,7H2

InChI Key

GRMSSCUVELGNHC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflav-2-enes

Direct Parent

Isoflavones

Alternative Parents

Substituents

Isoflavone
Hydroxyisoflavonoid
Chromone
Benzopyran
1-benzopyran
Benzodioxole
1-hydroxy-2-unsubstituted benzenoid
Pyranone
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Pyran
Heteroaromatic compound
Oxacycle
Organoheterocyclic compound
Acetal
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Isoflavonoids (LMPK12050085 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0033859)

Cellular substructure

Membrane (HMDB: HMDB0033859)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033859)

Source

Exogenous

Food

Food (HMDB: HMDB0033859)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0033859)

Not Available

Nutrient (HMDB: HMDB0033859)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	282.3 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.16 g/L	ALOGPS
logP	2.71	ALOGPS
logP	2.35	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	6.47	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.22 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	75.47 m³·mol⁻¹	ChemAxon
Polarizability	29.02 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	167.462	31661259
DarkChem	[M-H]-	167.684	31661259
DeepCCS	[M+H]+	171.952	30932474
DeepCCS	[M-H]-	169.594	30932474
DeepCCS	[M-2H]-	203.516	30932474
DeepCCS	[M+Na]+	178.768	30932474
AllCCS	[M+H]+	167.3	32859911
AllCCS	[M+H-H2O]+	163.6	32859911
AllCCS	[M+NH4]+	170.7	32859911
AllCCS	[M+Na]+	171.7	32859911
AllCCS	[M-H]-	168.5	32859911
AllCCS	[M+Na-2H]-	167.5	32859911
AllCCS	[M+HCOO]-	166.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Glyzaglabrin	OC1=CC2=C(C=C1)C(=O)C(=CO2)C1=C(O)C2=C(OCO2)C=C1	4078.1	Standard polar	33892256
Glyzaglabrin	OC1=CC2=C(C=C1)C(=O)C(=CO2)C1=C(O)C2=C(OCO2)C=C1	2768.5	Standard non polar	33892256
Glyzaglabrin	OC1=CC2=C(C=C1)C(=O)C(=CO2)C1=C(O)C2=C(OCO2)C=C1	3070.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Glyzaglabrin,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C2C(=O)C(C3=CC=C4OCOC4=C3O)=COC2=C1	2995.8	Semi standard non polar	33892256
Glyzaglabrin,1TMS,isomer #2	C[Si](C)(C)OC1=C(C2=COC3=CC(O)=CC=C3C2=O)C=CC2=C1OCO2	2977.8	Semi standard non polar	33892256
Glyzaglabrin,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C2C(=O)C(C3=CC=C4OCOC4=C3O[Si](C)(C)C)=COC2=C1	2952.2	Semi standard non polar	33892256
Glyzaglabrin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=O)C(C3=CC=C4OCOC4=C3O)=COC2=C1	3237.8	Semi standard non polar	33892256
Glyzaglabrin,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=C(C2=COC3=CC(O)=CC=C3C2=O)C=CC2=C1OCO2	3226.6	Semi standard non polar	33892256
Glyzaglabrin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=O)C(C3=CC=C4OCOC4=C3O[Si](C)(C)C(C)(C)C)=COC2=C1	3451.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Glyzaglabrin GC-MS (Non-derivatized) - 70eV, Positive	splash10-00xr-0290000000-1af27d28183f047e83b8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glyzaglabrin GC-MS (2 TMS) - 70eV, Positive	splash10-00di-6258900000-8f9afff93fed40e8d361	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glyzaglabrin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glyzaglabrin 10V, Positive-QTOF	splash10-0002-0090000000-5bda2756d0ddbfc4a0a3	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glyzaglabrin 20V, Positive-QTOF	splash10-0002-0090000000-920ea4d3542e248ab697	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glyzaglabrin 40V, Positive-QTOF	splash10-03g0-2590000000-c0ead0d703f631524f21	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glyzaglabrin 10V, Negative-QTOF	splash10-0002-0090000000-28ca22ce90df33e58ebb	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glyzaglabrin 20V, Negative-QTOF	splash10-0002-0090000000-aeb617a91b3117584d49	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glyzaglabrin 40V, Negative-QTOF	splash10-004r-4890000000-5075616fa31480d3af74	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glyzaglabrin 10V, Negative-QTOF	splash10-0002-0090000000-96de5c56a94c496da9f8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glyzaglabrin 20V, Negative-QTOF	splash10-0002-0090000000-ff73fa19df83630a66b7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glyzaglabrin 40V, Negative-QTOF	splash10-00or-0290000000-5b25734485ad1750b90b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glyzaglabrin 10V, Positive-QTOF	splash10-0002-0090000000-0e40d1dc69d66b601127	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glyzaglabrin 20V, Positive-QTOF	splash10-0002-0090000000-b9d731bcc7f1987e8394	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glyzaglabrin 40V, Positive-QTOF	splash10-00r2-0190000000-d1410e87c752015ed03a	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB012043

KNApSAcK ID

C00009399

Chemspider ID

4476529

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5317777

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1838871

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Glyzaglabrin (HMDB0033859)

MOL for HMDB0033859 (Glyzaglabrin)

3D MOL for HMDB0033859 (Glyzaglabrin)

3D SDF for HMDB0033859 (Glyzaglabrin)

3D-SDF for HMDB0033859 (Glyzaglabrin)

PDB for HMDB0033859 (Glyzaglabrin)

3D PDB for HMDB0033859 (Glyzaglabrin)

SMILES for HMDB0033859 (Glyzaglabrin)

INCHI for HMDB0033859 (Glyzaglabrin)

Structure for HMDB0033859 (Glyzaglabrin)

3D Structure for HMDB0033859 (Glyzaglabrin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra