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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:30:59 UTC

Update Date

2022-03-07 02:52:11 UTC

HMDB ID

HMDB0029533

Secondary Accession Numbers

HMDB29533

Metabolite Identification

Common Name

Glabrone

Description

Glabrone, also known as eurycarpin b, 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. Thus, glabrone is considered to be a flavonoid. Based on a literature review very few articles have been published on Glabrone.

Structure

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

HMDB0029533
     RDKit          3D
Glabrone
 41 44  0  0  0  0  0  0  0  0999 V2000
   -5.3037   -1.6200   -0.9394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7468   -0.4619   -0.0969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8788    0.0333    0.7919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2537    0.6083   -0.9740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9971    0.9858   -1.0487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0043    0.3298   -0.2296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3859   -0.6754    0.6217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4767   -1.3612    1.4354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1528   -1.0260    1.3890 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2455   -0.0172    0.5371 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6618    0.3435    0.5402 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1686    1.3642    1.2913 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4456    1.5979    1.2908 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3334    0.9046    0.5951 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6743    1.2015    0.6343 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5563    0.4518   -0.1085 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8974    0.7572   -0.0583 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0804   -0.5900   -0.8852 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7340   -0.8730   -0.9113 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8541   -0.1338   -0.1759 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5037   -0.4393   -0.2207 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0475   -1.3742   -0.9099 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6510    0.6657   -0.2690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2146    1.6780   -1.1122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7204   -1.0315    0.6800 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3435   -1.8235   -0.6491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1905   -1.3520   -2.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7085   -2.5511   -0.8027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5863    1.0438    1.1545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9728   -0.6418    1.6446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7992    0.1234    0.1806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9747    1.1161   -1.6007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7246    1.7782   -1.7224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8159   -2.1493    2.0976 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5981   -1.5399    2.0176 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4423    1.9502    1.8749 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0044    2.0093    1.2545 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3800    1.4004   -0.6564 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7622   -1.1892   -1.4767 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3498   -1.6808   -1.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8377    2.1881   -1.6977 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  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 10 23  2  0
 23 24  1  0
  7 25  1  0
 25  2  1  0
 23  6  1  0
 21 11  1  0
 20 14  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  5 33  1  0
  8 34  1  0
  9 35  1  0
 12 36  1  0
 15 37  1  0
 17 38  1  0
 18 39  1  0
 19 40  1  0
 24 41  1  0
M  END


  Mrv0541 02241212542D          

 25 28  0  0  0  0            999 V2000
   -3.3000    0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0145   -0.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0145   -1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3000   -1.5616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5855   -1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5855   -0.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8711    0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8711   -1.5616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1566   -1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1566   -0.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4421    0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2429    1.3259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4421    0.9134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2723   -0.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9868    0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9573    0.9134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9573    2.5635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2429    2.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6718    1.3259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6718    2.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0843    2.8654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4687    1.9374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1604    1.3193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7289   -1.5616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8711    0.9134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  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
  7  6  1  0  0  0  0
  6  5  2  0  0  0  0
  5  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 13 11  2  0  0  0  0
 11 14  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 18 12  1  0  0  0  0
 12 16  2  0  0  0  0
 16 19  1  0  0  0  0
 17 18  2  0  0  0  0
 17 20  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 13 23  1  0  0  0  0
  3 24  1  0  0  0  0
  7 25  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029533

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1(C)OC2=C(C=C1)C(O)=C(C=C2)C1=COC2=C(C=CC(O)=C2)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H16O5/c1-20(2)8-7-14-16(25-20)6-5-12(18(14)22)15-10-24-17-9-11(21)3-4-13(17)19(15)23/h3-10,21-22H,1-2H3

> <INCHI_KEY>
COLMVFWKLOZOOP-UHFFFAOYSA-N

> <FORMULA>
C20H16O5

> <MOLECULAR_WEIGHT>
336.338

> <EXACT_MASS>
336.099773622

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
35.433219152869

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-hydroxy-3-(5-hydroxy-2,2-dimethyl-2H-chromen-6-yl)-4H-chromen-4-one

> <ALOGPS_LOGP>
4.37

> <JCHEM_LOGP>
3.631061113333333

> <ALOGPS_LOGS>
-4.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.53014404611579

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.4691863068941595

> <JCHEM_PKA_STRONGEST_BASIC>
-4.778411389526237

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
94.0954

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.08e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
glabrone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029533
     RDKit          3D
Glabrone
 41 44  0  0  0  0  0  0  0  0999 V2000
   -5.3037   -1.6200   -0.9394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7468   -0.4619   -0.0969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8788    0.0333    0.7919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2537    0.6083   -0.9740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9971    0.9858   -1.0487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0043    0.3298   -0.2296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3859   -0.6754    0.6217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4767   -1.3612    1.4354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1528   -1.0260    1.3890 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2455   -0.0172    0.5371 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6618    0.3435    0.5402 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1686    1.3642    1.2913 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4456    1.5979    1.2908 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3334    0.9046    0.5951 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6743    1.2015    0.6343 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5563    0.4518   -0.1085 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8974    0.7572   -0.0583 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0804   -0.5900   -0.8852 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7340   -0.8730   -0.9113 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8541   -0.1338   -0.1759 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5037   -0.4393   -0.2207 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0475   -1.3742   -0.9099 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6510    0.6657   -0.2690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2146    1.6780   -1.1122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7204   -1.0315    0.6800 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3435   -1.8235   -0.6491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1905   -1.3520   -2.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7085   -2.5511   -0.8027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5863    1.0438    1.1545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9728   -0.6418    1.6446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7992    0.1234    0.1806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9747    1.1161   -1.6007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7246    1.7782   -1.7224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8159   -2.1493    2.0976 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5981   -1.5399    2.0176 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4423    1.9502    1.8749 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0044    2.0093    1.2545 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3800    1.4004   -0.6564 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7622   -1.1892   -1.4767 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3498   -1.6808   -1.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8377    2.1881   -1.6977 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  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 10 23  2  0
 23 24  1  0
  7 25  1  0
 25  2  1  0
 23  6  1  0
 21 11  1  0
 20 14  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  5 33  1  0
  8 34  1  0
  9 35  1  0
 12 36  1  0
 15 37  1  0
 17 38  1  0
 18 39  1  0
 19 40  1  0
 24 41  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -6.160   0.165   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.494  -0.605   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.494  -2.145   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.160  -2.915   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.826  -2.145   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.826  -0.605   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.493   0.165   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -3.493  -2.915   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.159  -2.145   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.159  -0.605   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.825   0.165   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.453   2.475   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.825   1.705   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.508  -0.605   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.842   0.165   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.787   1.705   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.787   4.785   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.453   4.015   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.121   2.475   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.121   4.015   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.891   5.349   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.608   3.616   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.166   2.463   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -8.827  -2.915   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -3.493   1.705   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   24                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    1    7    5                                                  
CONECT    7    6   10   25                                                  
CONECT    8    5    9                                                       
CONECT    9    8   10                                                       
CONECT   10    7    9   11                                                  
CONECT   11   10   13   14                                                  
CONECT   12   13   18   16                                                  
CONECT   13   11   12   23                                                  
CONECT   14   11   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   12   19                                                  
CONECT   17   18   20                                                       
CONECT   18   12   17                                                       
CONECT   19   16   20                                                       
CONECT   20   17   19   21   22                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   13                                                            
CONECT   24    3                                                            
CONECT   25    7                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

COMPND    HMDB0029533
HETATM    1  C1  UNL     1      -5.304  -1.620  -0.939  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.747  -0.462  -0.097  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.879   0.033   0.792  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.254   0.608  -0.974  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.997   0.986  -1.049  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.004   0.330  -0.230  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.386  -0.675   0.622  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.477  -1.361   1.435  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.153  -1.026   1.389  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.246  -0.017   0.537  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.662   0.344   0.540  1.00  0.00           C  
HETATM   12  C12 UNL     1       2.169   1.364   1.291  1.00  0.00           C  
HETATM   13  O1  UNL     1       3.446   1.598   1.291  1.00  0.00           O  
HETATM   14  C13 UNL     1       4.333   0.905   0.595  1.00  0.00           C  
HETATM   15  C14 UNL     1       5.674   1.201   0.634  1.00  0.00           C  
HETATM   16  C15 UNL     1       6.556   0.452  -0.108  1.00  0.00           C  
HETATM   17  O2  UNL     1       7.897   0.757  -0.058  1.00  0.00           O  
HETATM   18  C16 UNL     1       6.080  -0.590  -0.885  1.00  0.00           C  
HETATM   19  C17 UNL     1       4.734  -0.873  -0.911  1.00  0.00           C  
HETATM   20  C18 UNL     1       3.854  -0.134  -0.176  1.00  0.00           C  
HETATM   21  C19 UNL     1       2.504  -0.439  -0.221  1.00  0.00           C  
HETATM   22  O3  UNL     1       2.048  -1.374  -0.910  1.00  0.00           O  
HETATM   23  C20 UNL     1      -0.651   0.666  -0.269  1.00  0.00           C  
HETATM   24  O4  UNL     1      -0.215   1.678  -1.112  1.00  0.00           O  
HETATM   25  O5  UNL     1      -3.720  -1.031   0.680  1.00  0.00           O  
HETATM   26  H1  UNL     1      -6.343  -1.823  -0.649  1.00  0.00           H  
HETATM   27  H2  UNL     1      -5.191  -1.352  -2.009  1.00  0.00           H  
HETATM   28  H3  UNL     1      -4.708  -2.551  -0.803  1.00  0.00           H  
HETATM   29  H4  UNL     1      -5.586   1.044   1.155  1.00  0.00           H  
HETATM   30  H5  UNL     1      -5.973  -0.642   1.645  1.00  0.00           H  
HETATM   31  H6  UNL     1      -6.799   0.123   0.181  1.00  0.00           H  
HETATM   32  H7  UNL     1      -4.975   1.116  -1.601  1.00  0.00           H  
HETATM   33  H8  UNL     1      -2.725   1.778  -1.722  1.00  0.00           H  
HETATM   34  H9  UNL     1      -1.816  -2.149   2.098  1.00  0.00           H  
HETATM   35  H10 UNL     1       0.598  -1.540   2.018  1.00  0.00           H  
HETATM   36  H11 UNL     1       1.442   1.950   1.875  1.00  0.00           H  
HETATM   37  H12 UNL     1       6.004   2.009   1.255  1.00  0.00           H  
HETATM   38  H13 UNL     1       8.380   1.400  -0.656  1.00  0.00           H  
HETATM   39  H14 UNL     1       6.762  -1.189  -1.477  1.00  0.00           H  
HETATM   40  H15 UNL     1       4.350  -1.681  -1.514  1.00  0.00           H  
HETATM   41  H16 UNL     1      -0.838   2.188  -1.698  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3    4   25
CONECT    3   29   30   31
CONECT    4    5    5   32
CONECT    5    6   33
CONECT    6    7    7   23
CONECT    7    8   25
CONECT    8    9    9   34
CONECT    9   10   35
CONECT   10   11   23   23
CONECT   11   12   12   21
CONECT   12   13   36
CONECT   13   14
CONECT   14   15   15   20
CONECT   15   16   37
CONECT   16   17   18   18
CONECT   17   38
CONECT   18   19   39
CONECT   19   20   20   40
CONECT   20   21
CONECT   21   22   22
CONECT   23   24
CONECT   24   41
END

HMDB0029533
     RDKit          3D
Glabrone
 41 44  0  0  0  0  0  0  0  0999 V2000
   -5.3037   -1.6200   -0.9394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7468   -0.4619   -0.0969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8788    0.0333    0.7919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2537    0.6083   -0.9740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9971    0.9858   -1.0487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0043    0.3298   -0.2296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3859   -0.6754    0.6217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4767   -1.3612    1.4354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1528   -1.0260    1.3890 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2455   -0.0172    0.5371 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6618    0.3435    0.5402 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1686    1.3642    1.2913 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4456    1.5979    1.2908 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3334    0.9046    0.5951 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6743    1.2015    0.6343 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5563    0.4518   -0.1085 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8974    0.7572   -0.0583 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0804   -0.5900   -0.8852 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7340   -0.8730   -0.9113 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8541   -0.1338   -0.1759 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5037   -0.4393   -0.2207 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0475   -1.3742   -0.9099 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6510    0.6657   -0.2690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2146    1.6780   -1.1122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7204   -1.0315    0.6800 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3435   -1.8235   -0.6491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1905   -1.3520   -2.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7085   -2.5511   -0.8027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5863    1.0438    1.1545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9728   -0.6418    1.6446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7992    0.1234    0.1806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9747    1.1161   -1.6007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7246    1.7782   -1.7224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8159   -2.1493    2.0976 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5981   -1.5399    2.0176 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4423    1.9502    1.8749 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0044    2.0093    1.2545 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3800    1.4004   -0.6564 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7622   -1.1892   -1.4767 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3498   -1.6808   -1.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8377    2.1881   -1.6977 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  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 10 23  2  0
 23 24  1  0
  7 25  1  0
 25  2  1  0
 23  6  1  0
 21 11  1  0
 20 14  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  5 33  1  0
  8 34  1  0
  9 35  1  0
 12 36  1  0
 15 37  1  0
 17 38  1  0
 18 39  1  0
 19 40  1  0
 24 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
7-Hydroxy-3-(5-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-yl)-4H-1-benzopyran-4-one, 9ci	HMDB
Eurycarpin b	HMDB
Morusin hydroperoxide	HMDB
7,2'-Dihydroxy-6'',6''-dimethylpyrano-(2'',3''-4',3')isoflavone	HMDB

Chemical Formula

C₂₀H₁₆O₅

Average Molecular Weight

336.338

Monoisotopic Molecular Weight

336.099773622

IUPAC Name

7-hydroxy-3-(5-hydroxy-2,2-dimethyl-2H-chromen-6-yl)-4H-chromen-4-one

Traditional Name

glabrone

CAS Registry Number

60008-02-8

SMILES

CC1(C)OC2=C(C=C1)C(O)=C(C=C2)C1=COC2=C(C=CC(O)=C2)C1=O

InChI Identifier

InChI=1S/C20H16O5/c1-20(2)8-7-14-16(25-20)6-5-12(18(14)22)15-10-24-17-9-11(21)3-4-13(17)19(15)23/h3-10,21-22H,1-2H3

InChI Key

COLMVFWKLOZOOP-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
Isoflavone
Hydroxyisoflavonoid
2,2-dimethyl-1-benzopyran
Chromone
Benzopyran
1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Pyran
Heteroaromatic compound
Ether
Oxacycle
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Isoflavonoids (LMPK12050074 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0029533)
Cell membrane (HMDB: HMDB0029533)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029533)

Source

Endogenous

Endogenous (HMDB: HMDB0029533)

Plant

Plant (HMDB: HMDB0029533)

Exogenous

Food

Food (HMDB: HMDB0029533)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0029533)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	224 - 226 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	7.22 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	0.011 g/L	ALOGPS
logP	4.37	ALOGPS
logP	3.63	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	6.47	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	94.1 m³·mol⁻¹	ChemAxon
Polarizability	35.43 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]+	179.018	31661259
DarkChem	[M-H]-	177.903	31661259
DeepCCS	[M+H]+	182.577	30932474
DeepCCS	[M-H]-	180.219	30932474
DeepCCS	[M-2H]-	214.222	30932474
DeepCCS	[M+Na]+	189.45	30932474
AllCCS	[M+H]+	180.9	32859911
AllCCS	[M+H-H2O]+	177.5	32859911
AllCCS	[M+NH4]+	184.1	32859911
AllCCS	[M+Na]+	185.0	32859911
AllCCS	[M-H]-	181.6	32859911
AllCCS	[M+Na-2H]-	180.9	32859911
AllCCS	[M+HCOO]-	180.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.56 minutes	32390414
Predicted by Siyang on May 30, 2022	12.3829 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.85 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	28.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2305.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	262.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	175.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	175.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	176.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	631.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	586.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	198.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1108.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	426.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1254.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	440.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	395.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	338.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	253.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	10.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Glabrone	CC1(C)OC2=C(C=C1)C(O)=C(C=C2)C1=COC2=C(C=CC(O)=C2)C1=O	4006.6	Standard polar	33892256
Glabrone	CC1(C)OC2=C(C=C1)C(O)=C(C=C2)C1=COC2=C(C=CC(O)=C2)C1=O	2877.2	Standard non polar	33892256
Glabrone	CC1(C)OC2=C(C=C1)C(O)=C(C=C2)C1=COC2=C(C=CC(O)=C2)C1=O	3270.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Glabrone,1TMS,isomer #1	CC1(C)C=CC2=C(C=CC(C3=COC4=CC(O)=CC=C4C3=O)=C2O[Si](C)(C)C)O1	3166.1	Semi standard non polar	33892256
Glabrone,1TMS,isomer #2	CC1(C)C=CC2=C(C=CC(C3=COC4=CC(O[Si](C)(C)C)=CC=C4C3=O)=C2O)O1	3151.4	Semi standard non polar	33892256
Glabrone,2TMS,isomer #1	CC1(C)C=CC2=C(C=CC(C3=COC4=CC(O[Si](C)(C)C)=CC=C4C3=O)=C2O[Si](C)(C)C)O1	3016.9	Semi standard non polar	33892256
Glabrone,1TBDMS,isomer #1	CC1(C)C=CC2=C(C=CC(C3=COC4=CC(O)=CC=C4C3=O)=C2O[Si](C)(C)C(C)(C)C)O1	3390.7	Semi standard non polar	33892256
Glabrone,1TBDMS,isomer #2	CC1(C)C=CC2=C(C=CC(C3=COC4=CC(O[Si](C)(C)C(C)(C)C)=CC=C4C3=O)=C2O)O1	3384.5	Semi standard non polar	33892256
Glabrone,2TBDMS,isomer #1	CC1(C)C=CC2=C(C=CC(C3=COC4=CC(O[Si](C)(C)C(C)(C)C)=CC=C4C3=O)=C2O[Si](C)(C)C(C)(C)C)O1	3513.1	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 - Glabrone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-0239000000-02cdbb828adf59f8e9ea	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glabrone GC-MS (2 TMS) - 70eV, Positive	splash10-00xr-2253900000-f6bfe8e93085c4a37517	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glabrone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glabrone 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 - Glabrone 10V, Positive-QTOF	splash10-000i-0009000000-fc949cee3880d9c2ab1f	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glabrone 20V, Positive-QTOF	splash10-000i-0039000000-1edd6131ef24c47e4806	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glabrone 40V, Positive-QTOF	splash10-0fts-5691000000-ad71d104a59d05ec8c59	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glabrone 10V, Negative-QTOF	splash10-000i-0009000000-4afa58f64fe760256bc1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glabrone 20V, Negative-QTOF	splash10-000i-0009000000-e43df9b15069f6af971f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glabrone 40V, Negative-QTOF	splash10-014r-2895000000-e8a10eca75882be56255	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glabrone 10V, Negative-QTOF	splash10-000i-0009000000-dc81427ba733f47873d1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glabrone 20V, Negative-QTOF	splash10-000i-0019000000-c2ab3766f57ecce69cb8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glabrone 40V, Negative-QTOF	splash10-0006-0091000000-759b8e8f1fed3a4e82b8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glabrone 10V, Positive-QTOF	splash10-000i-0009000000-515a0c5934a26e5d5bd9	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glabrone 20V, Positive-QTOF	splash10-000i-0039000000-38059c03312539ee043e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glabrone 40V, Positive-QTOF	splash10-004i-1191000000-5158d69189a52fff5aec	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

FDB000674

KNApSAcK ID

C00009434

Chemspider ID

4476468

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5317652

PDB ID

Not Available

ChEBI ID

698651

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1810261

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 Glabrone (HMDB0029533)

MOL for HMDB0029533 (Glabrone)

3D MOL for HMDB0029533 (Glabrone)

3D SDF for HMDB0029533 (Glabrone)

3D-SDF for HMDB0029533 (Glabrone)

PDB for HMDB0029533 (Glabrone)

3D PDB for HMDB0029533 (Glabrone)

SMILES for HMDB0029533 (Glabrone)

INCHI for HMDB0029533 (Glabrone)

Structure for HMDB0029533 (Glabrone)

3D Structure for HMDB0029533 (Glabrone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra