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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 18:58:56 UTC

Update Date

2022-09-22 18:34:25 UTC

HMDB ID

HMDB0034188

Secondary Accession Numbers

HMDB34188

Metabolite Identification

Common Name

(R)-Glabridin

Description

(R)-Glabridin belongs to the class of organic compounds known as pyranoisoflavonoids. These are isoflavonoids that contain a pyran ring fused to either of the A, B, or C ring of the isoflavonoid skeleton (R)-Glabridin has been detected, but not quantified in, several different foods, such as green tea, black tea, herbal tea, red tea, and herbs and spices. This could make (R)-glabridin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on (R)-Glabridin.

Structure

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

HMDB0034188
     RDKit          3D
(R)-Glabridin
 44 47  0  0  0  0  0  0  0  0999 V2000
   -5.5121    1.2041   -1.4043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8535    0.1557   -0.4897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9720   -0.6440    0.1232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0091   -0.7578   -1.3168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7038   -0.8490   -1.2122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0290    0.0030   -0.2118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7802    0.8423    0.5803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0961    1.6368    1.4949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7342    1.5816    1.5893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0046    0.7454    0.7874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6345   -0.0630   -0.1226 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1245   -0.9240   -0.9240 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2282   -1.6075   -0.2373 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0013   -0.6314    0.5680 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4492   -0.6338    0.3538 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2936   -1.2991    1.2224 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6691   -1.1566    1.1596 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2550   -0.3353    0.2141 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6421   -0.1498    0.1105 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4080    0.3409   -0.6726 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0352    0.1920   -0.5990 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2129    0.8881   -1.5233 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4840    0.7189    0.8138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1350    0.8867    0.4560 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7331    1.8641   -1.8660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0903    1.8785   -0.6924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2298    0.7618   -2.0834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9296   -0.4826   -0.4734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1567   -0.4057    1.1751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7945   -1.7433    0.0347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5335   -1.3640   -2.0525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0821   -1.5080   -1.8218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6961    2.2864    2.1206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1804    2.1946    2.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8289   -2.0400   -1.0863 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7726   -2.4342    0.3027 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9069   -1.1242    1.6790 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9602   -1.9755    1.9991 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3400   -1.6693    1.8241 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1171    0.5862    0.6163 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8452    1.0006   -1.4462 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6608    1.4798   -2.1937 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8354    1.5023    0.1065 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8202    1.0486    1.8600 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  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
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 14 23  1  0
  7 24  1  0
 24  2  1  0
 11  6  1  0
 21 15  1  0
 23 10  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  8 33  1  0
  9 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 16 38  1  0
 17 39  1  0
 19 40  1  0
 20 41  1  0
 22 42  1  0
 23 43  1  0
 23 44  1  0
M  END

  Mrv0541 05061307382D          

 24 27  0  0  0  0            999 V2000
    4.6465    0.9428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6465   -0.1178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5855    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4105    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  6  3  2  0  0  0  0
  8  7  2  0  0  0  0
 12  3  1  0  0  0  0
 12  9  1  0  0  0  0
 13  9  1  0  0  0  0
 13 11  1  0  0  0  0
 14  4  1  0  0  0  0
 14 10  2  0  0  0  0
 15  5  1  0  0  0  0
 15 13  1  0  0  0  0
 16  7  1  0  0  0  0
 17 10  1  0  0  0  0
 17 15  2  0  0  0  0
 18  6  1  0  0  0  0
 18 16  2  0  0  0  0
 19 12  2  0  0  0  0
 19 16  1  0  0  0  0
 20  1  1  0  0  0  0
 20  2  1  0  0  0  0
 20  8  1  0  0  0  0
 21 14  1  0  0  0  0
 22 17  1  0  0  0  0
 23 11  1  0  0  0  0
 23 19  1  0  0  0  0
 24 18  1  0  0  0  0
 24 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034188

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1(C)OC2=C(C=C1)C1=C(CC(CO1)C1=C(O)C=C(O)C=C1)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C20H20O4/c1-20(2)8-7-16-18(24-20)6-3-12-9-13(11-23-19(12)16)15-5-4-14(21)10-17(15)22/h3-8,10,13,21-22H,9,11H2,1-2H3

> <INCHI_KEY>
LBQIJVLKGVZRIW-UHFFFAOYSA-N

> <FORMULA>
C20H20O4

> <MOLECULAR_WEIGHT>
324.3704

> <EXACT_MASS>
324.136159128

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
34.70332244758664

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-{8,8-dimethyl-2H,3H,4H,8H-pyrano[2,3-f]chromen-3-yl}benzene-1,3-diol

> <ALOGPS_LOGP>
3.81

> <JCHEM_LOGP>
4.092301279333332

> <ALOGPS_LOGS>
-4.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.859613955113344

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.516526753486659

> <JCHEM_PKA_STRONGEST_BASIC>
-4.58598679058369

> <JCHEM_POLAR_SURFACE_AREA>
58.92

> <JCHEM_REFRACTIVITY>
93.35359999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.26e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-{8,8-dimethyl-2H,3H,4H-pyrano[2,3-f]chromen-3-yl}benzene-1,3-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034188
     RDKit          3D
(R)-Glabridin
 44 47  0  0  0  0  0  0  0  0999 V2000
   -5.5121    1.2041   -1.4043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8535    0.1557   -0.4897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9720   -0.6440    0.1232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0091   -0.7578   -1.3168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7038   -0.8490   -1.2122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0290    0.0030   -0.2118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7802    0.8423    0.5803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0961    1.6368    1.4949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7342    1.5816    1.5893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0046    0.7454    0.7874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6345   -0.0630   -0.1226 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1245   -0.9240   -0.9240 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2282   -1.6075   -0.2373 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0013   -0.6314    0.5680 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4492   -0.6338    0.3538 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2936   -1.2991    1.2224 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6691   -1.1566    1.1596 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2550   -0.3353    0.2141 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6421   -0.1498    0.1105 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4080    0.3409   -0.6726 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0352    0.1920   -0.5990 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2129    0.8881   -1.5233 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4840    0.7189    0.8138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1350    0.8867    0.4560 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7331    1.8641   -1.8660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0903    1.8785   -0.6924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2298    0.7618   -2.0834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9296   -0.4826   -0.4734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1567   -0.4057    1.1751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7945   -1.7433    0.0347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5335   -1.3640   -2.0525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0821   -1.5080   -1.8218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6961    2.2864    2.1206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1804    2.1946    2.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8289   -2.0400   -1.0863 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7726   -2.4342    0.3027 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9069   -1.1242    1.6790 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9602   -1.9755    1.9991 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3400   -1.6693    1.8241 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1171    0.5862    0.6163 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8452    1.0006   -1.4462 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6608    1.4798   -2.1937 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8354    1.5023    0.1065 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8202    1.0486    1.8600 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  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
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 14 23  1  0
  7 24  1  0
 24  2  1  0
 11  6  1  0
 21 15  1  0
 23 10  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  8 33  1  0
  9 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 16 38  1  0
 17 39  1  0
 19 40  1  0
 20 41  1  0
 22 42  1  0
 23 43  1  0
 23 44  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       8.673   1.760   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.673  -0.220   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.056  -0.564   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.516  -0.564   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.056   2.104   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.826   0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.746   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.516   2.104   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -6.366   0.770   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -1.746   3.437   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       2.104   2.104   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       6.724  -0.564   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2   20                                                            
CONECT    3    6   12                                                       
CONECT    4    5   14                                                       
CONECT    5    4   15                                                       
CONECT    6    3   18                                                       
CONECT    7    8   16                                                       
CONECT    8    7   20                                                       
CONECT    9   12   13                                                       
CONECT   10   14   17                                                       
CONECT   11   13   23                                                       
CONECT   12    3    9   19                                                  
CONECT   13    9   11   15                                                  
CONECT   14    4   10   21                                                  
CONECT   15    5   13   17                                                  
CONECT   16    7   18   19                                                  
CONECT   17   10   15   22                                                  
CONECT   18    6   16   24                                                  
CONECT   19   12   16   23                                                  
CONECT   20    1    2    8   24                                             
CONECT   21   14                                                            
CONECT   22   17                                                            
CONECT   23   11   19                                                       
CONECT   24   18   20                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    HMDB0034188
HETATM    1  C1  UNL     1      -5.512   1.204  -1.404  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.853   0.156  -0.490  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.972  -0.644   0.123  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.009  -0.758  -1.317  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.704  -0.849  -1.212  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.029   0.003  -0.212  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.780   0.842   0.580  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.096   1.637   1.495  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.734   1.582   1.589  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.005   0.745   0.787  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.634  -0.063  -0.123  1.00  0.00           C  
HETATM   12  O1  UNL     1       0.124  -0.924  -0.924  1.00  0.00           O  
HETATM   13  C12 UNL     1       1.228  -1.608  -0.237  1.00  0.00           C  
HETATM   14  C13 UNL     1       2.001  -0.631   0.568  1.00  0.00           C  
HETATM   15  C14 UNL     1       3.449  -0.634   0.354  1.00  0.00           C  
HETATM   16  C15 UNL     1       4.294  -1.299   1.222  1.00  0.00           C  
HETATM   17  C16 UNL     1       5.669  -1.157   1.160  1.00  0.00           C  
HETATM   18  C17 UNL     1       6.255  -0.335   0.214  1.00  0.00           C  
HETATM   19  O2  UNL     1       7.642  -0.150   0.110  1.00  0.00           O  
HETATM   20  C18 UNL     1       5.408   0.341  -0.673  1.00  0.00           C  
HETATM   21  C19 UNL     1       4.035   0.192  -0.599  1.00  0.00           C  
HETATM   22  O3  UNL     1       3.213   0.888  -1.523  1.00  0.00           O  
HETATM   23  C20 UNL     1       1.484   0.719   0.814  1.00  0.00           C  
HETATM   24  O4  UNL     1      -4.135   0.887   0.456  1.00  0.00           O  
HETATM   25  H1  UNL     1      -4.733   1.864  -1.866  1.00  0.00           H  
HETATM   26  H2  UNL     1      -6.090   1.878  -0.692  1.00  0.00           H  
HETATM   27  H3  UNL     1      -6.230   0.762  -2.083  1.00  0.00           H  
HETATM   28  H4  UNL     1      -6.930  -0.483  -0.473  1.00  0.00           H  
HETATM   29  H5  UNL     1      -6.157  -0.406   1.175  1.00  0.00           H  
HETATM   30  H6  UNL     1      -5.794  -1.743   0.035  1.00  0.00           H  
HETATM   31  H7  UNL     1      -4.534  -1.364  -2.053  1.00  0.00           H  
HETATM   32  H8  UNL     1      -2.082  -1.508  -1.822  1.00  0.00           H  
HETATM   33  H9  UNL     1      -2.696   2.286   2.121  1.00  0.00           H  
HETATM   34  H10 UNL     1      -0.180   2.195   2.280  1.00  0.00           H  
HETATM   35  H11 UNL     1       1.829  -2.040  -1.086  1.00  0.00           H  
HETATM   36  H12 UNL     1       0.773  -2.434   0.303  1.00  0.00           H  
HETATM   37  H13 UNL     1       1.907  -1.124   1.679  1.00  0.00           H  
HETATM   38  H14 UNL     1       3.960  -1.975   1.999  1.00  0.00           H  
HETATM   39  H15 UNL     1       6.340  -1.669   1.824  1.00  0.00           H  
HETATM   40  H16 UNL     1       8.117   0.586   0.616  1.00  0.00           H  
HETATM   41  H17 UNL     1       5.845   1.001  -1.446  1.00  0.00           H  
HETATM   42  H18 UNL     1       3.661   1.480  -2.194  1.00  0.00           H  
HETATM   43  H19 UNL     1       1.835   1.502   0.107  1.00  0.00           H  
HETATM   44  H20 UNL     1       1.820   1.049   1.860  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    4   24
CONECT    3   28   29   30
CONECT    4    5    5   31
CONECT    5    6   32
CONECT    6    7    7   11
CONECT    7    8   24
CONECT    8    9    9   33
CONECT    9   10   34
CONECT   10   11   11   23
CONECT   11   12
CONECT   12   13
CONECT   13   14   35   36
CONECT   14   15   23   37
CONECT   15   16   16   21
CONECT   16   17   38
CONECT   17   18   18   39
CONECT   18   19   20
CONECT   19   40
CONECT   20   21   21   41
CONECT   21   22
CONECT   22   42
CONECT   23   43   44
END

HMDB0034188
     RDKit          3D
(R)-Glabridin
 44 47  0  0  0  0  0  0  0  0999 V2000
   -5.5121    1.2041   -1.4043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8535    0.1557   -0.4897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9720   -0.6440    0.1232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0091   -0.7578   -1.3168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7038   -0.8490   -1.2122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0290    0.0030   -0.2118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7802    0.8423    0.5803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0961    1.6368    1.4949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7342    1.5816    1.5893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0046    0.7454    0.7874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6345   -0.0630   -0.1226 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1245   -0.9240   -0.9240 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2282   -1.6075   -0.2373 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0013   -0.6314    0.5680 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4492   -0.6338    0.3538 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2936   -1.2991    1.2224 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6691   -1.1566    1.1596 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2550   -0.3353    0.2141 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6421   -0.1498    0.1105 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4080    0.3409   -0.6726 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0352    0.1920   -0.5990 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2129    0.8881   -1.5233 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4840    0.7189    0.8138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1350    0.8867    0.4560 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7331    1.8641   -1.8660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0903    1.8785   -0.6924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2298    0.7618   -2.0834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9296   -0.4826   -0.4734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1567   -0.4057    1.1751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7945   -1.7433    0.0347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5335   -1.3640   -2.0525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0821   -1.5080   -1.8218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6961    2.2864    2.1206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1804    2.1946    2.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8289   -2.0400   -1.0863 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7726   -2.4342    0.3027 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9069   -1.1242    1.6790 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9602   -1.9755    1.9991 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3400   -1.6693    1.8241 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1171    0.5862    0.6163 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8452    1.0006   -1.4462 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6608    1.4798   -2.1937 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8354    1.5023    0.1065 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8202    1.0486    1.8600 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  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
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 14 23  1  0
  7 24  1  0
 24  2  1  0
 11  6  1  0
 21 15  1  0
 23 10  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  8 33  1  0
  9 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 16 38  1  0
 17 39  1  0
 19 40  1  0
 20 41  1  0
 22 42  1  0
 23 43  1  0
 23 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Glabridin	HMDB

Chemical Formula

C₂₀H₂₀O₄

Average Molecular Weight

324.3704

Monoisotopic Molecular Weight

324.136159128

IUPAC Name

4-{8,8-dimethyl-2H,3H,4H,8H-pyrano[2,3-f]chromen-3-yl}benzene-1,3-diol

Traditional Name

4-{8,8-dimethyl-2H,3H,4H-pyrano[2,3-f]chromen-3-yl}benzene-1,3-diol

CAS Registry Number

59870-68-7

SMILES

CC1(C)OC2=C(C=C1)C1=C(CC(CO1)C1=C(O)C=C(O)C=C1)C=C2

InChI Identifier

InChI=1S/C20H20O4/c1-20(2)8-7-16-18(24-20)6-3-12-9-13(11-23-19(12)16)15-5-4-14(21)10-17(15)22/h3-8,10,13,21-22H,9,11H2,1-2H3

InChI Key

LBQIJVLKGVZRIW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranoisoflavonoids. These are isoflavonoids that contain a pyran ring fused to either of the A, B, or C ring of the isoflavonoid skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Pyranoisoflavonoids

Direct Parent

Pyranoisoflavonoids

Alternative Parents

Substituents

Pyranoisoflavonoid
Hydroxyisoflavonoid
Isoflavanol
Isoflavan
Pyranochromene
2,2-dimethyl-1-benzopyran
Chromane
Benzopyran
1-benzopyran
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0034188)
Cell membrane (HMDB: HMDB0034188)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034188)

Source

Exogenous

Exogenous (HMDB: HMDB0034188)

Food

Food (HMDB: HMDB0034188)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0034188)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0034188)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	154 - 155 °C	Not Available
Boiling Point	518.60 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0.93 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	4.260 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0093 g/L	ALOGPS
logP	3.81	ALOGPS
logP	4.09	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	9.52	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.92 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	93.35 m³·mol⁻¹	ChemAxon
Polarizability	34.7 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]+	177.663	31661259
DarkChem	[M-H]-	178.162	31661259
DeepCCS	[M+H]+	184.188	30932474
DeepCCS	[M-H]-	181.83	30932474
DeepCCS	[M-2H]-	216.03	30932474
DeepCCS	[M+Na]+	191.44	30932474
AllCCS	[M+H]+	179.9	32859911
AllCCS	[M+H-H2O]+	176.5	32859911
AllCCS	[M+NH4]+	183.1	32859911
AllCCS	[M+Na]+	184.0	32859911
AllCCS	[M-H]-	183.5	32859911
AllCCS	[M+Na-2H]-	183.0	32859911
AllCCS	[M+HCOO]-	182.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(R)-Glabridin	CC1(C)OC2=C(C=C1)C1=C(CC(CO1)C1=C(O)C=C(O)C=C1)C=C2	3766.4	Standard polar	33892256
(R)-Glabridin	CC1(C)OC2=C(C=C1)C1=C(CC(CO1)C1=C(O)C=C(O)C=C1)C=C2	2896.0	Standard non polar	33892256
(R)-Glabridin	CC1(C)OC2=C(C=C1)C1=C(CC(CO1)C1=C(O)C=C(O)C=C1)C=C2	3173.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(R)-Glabridin,1TMS,isomer #1	CC1(C)C=CC2=C(C=CC3=C2OCC(C2=CC=C(O)C=C2O[Si](C)(C)C)C3)O1	2859.1	Semi standard non polar	33892256
(R)-Glabridin,1TMS,isomer #2	CC1(C)C=CC2=C(C=CC3=C2OCC(C2=CC=C(O[Si](C)(C)C)C=C2O)C3)O1	2894.1	Semi standard non polar	33892256
(R)-Glabridin,2TMS,isomer #1	CC1(C)C=CC2=C(C=CC3=C2OCC(C2=CC=C(O[Si](C)(C)C)C=C2O[Si](C)(C)C)C3)O1	2774.8	Semi standard non polar	33892256
(R)-Glabridin,1TBDMS,isomer #1	CC1(C)C=CC2=C(C=CC3=C2OCC(C2=CC=C(O)C=C2O[Si](C)(C)C(C)(C)C)C3)O1	3124.7	Semi standard non polar	33892256
(R)-Glabridin,1TBDMS,isomer #2	CC1(C)C=CC2=C(C=CC3=C2OCC(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2O)C3)O1	3168.2	Semi standard non polar	33892256
(R)-Glabridin,2TBDMS,isomer #1	CC1(C)C=CC2=C(C=CC3=C2OCC(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2O[Si](C)(C)C(C)(C)C)C3)O1	3232.6	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 - (R)-Glabridin GC-MS (Non-derivatized) - 70eV, Positive	splash10-05fr-0986000000-a402c5b6e8c58929f3c9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Glabridin GC-MS (2 TMS) - 70eV, Positive	splash10-0udi-3459800000-a946a115c0381a514541	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Glabridin 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 - (R)-Glabridin 10V, Positive-QTOF	splash10-004r-1829000000-4f7978527f8f0227426e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Glabridin 20V, Positive-QTOF	splash10-000i-1954000000-3100d85b046e6a2b3d97	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Glabridin 40V, Positive-QTOF	splash10-00kr-3920000000-63380871cd9494383eb4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Glabridin 10V, Negative-QTOF	splash10-00di-0319000000-aa71f3a8c3f10d8f0067	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Glabridin 20V, Negative-QTOF	splash10-05fr-1967000000-16a39bd697ce2e038736	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Glabridin 40V, Negative-QTOF	splash10-0a4r-1930000000-c0c1123cde5ce6028080	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Glabridin 10V, Negative-QTOF	splash10-00di-0009000000-b64caba2598a2db6662e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Glabridin 20V, Negative-QTOF	splash10-05gi-2069000000-4c00c7aa5fb9df7307f6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Glabridin 40V, Negative-QTOF	splash10-0as0-4592000000-252b77c9d4eace96e92a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Glabridin 10V, Positive-QTOF	splash10-004i-0039000000-1f47f6bebdc38361425c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Glabridin 20V, Positive-QTOF	splash10-004i-0069000000-04dcce05f2db2252e85d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Glabridin 40V, Positive-QTOF	splash10-0abj-1692000000-f247596537c4ed45bb1f	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

4484219

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1700451

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.. .

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

(R)-Glabridin → 6-(4-{8,8-dimethyl-2H,3H,4H,8H-pyrano[2,3-f]chromen-3-yl}-3-hydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid	details
(R)-Glabridin → 6-(2-{8,8-dimethyl-2H,3H,4H,8H-pyrano[2,3-f]chromen-3-yl}-5-hydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid	details

Showing metabocard for (R)-Glabridin (HMDB0034188)

MOL for HMDB0034188 ((R)-Glabridin)

3D MOL for HMDB0034188 ((R)-Glabridin)

3D SDF for HMDB0034188 ((R)-Glabridin)

3D-SDF for HMDB0034188 ((R)-Glabridin)

PDB for HMDB0034188 ((R)-Glabridin)

3D PDB for HMDB0034188 ((R)-Glabridin)

SMILES for HMDB0034188 ((R)-Glabridin)

INCHI for HMDB0034188 ((R)-Glabridin)

Structure for HMDB0034188 ((R)-Glabridin)

3D Structure for HMDB0034188 ((R)-Glabridin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions