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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:48:33 UTC

Update Date

2022-03-07 02:53:57 UTC

HMDB ID

HMDB0034034

Secondary Accession Numbers

HMDB34034

Metabolite Identification

Common Name

Bikojic acid

Description

Bikojic acid, also known as bgy-F compound or bikojate, belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone. Bikojic acid has been detected, but not quantified in, fats and oils. This could make bikojic acid a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Bikojic acid.

Structure

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

HMDB0034034
     RDKit          3D
Bikojic acid
 30 31  0  0  0  0  0  0  0  0999 V2000
    3.7549   -0.0838    2.1705 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9681   -0.0999    1.2067 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3552   -0.0971   -0.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4306   -0.1156   -1.1258 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8688   -0.1113   -2.5662 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2563   -0.0874   -2.5875 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1805   -0.1367   -0.8003 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7008   -0.1424    0.4634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7477   -0.1630    0.6073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3959    0.2767   -0.4826 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6856    0.3451   -0.5466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4054    0.8396   -1.7729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5962    2.2015   -1.7063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4111   -0.0479    0.5432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8215   -0.5097    1.6928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4441   -0.8800    2.7142 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4109   -0.5628    1.7028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7811   -1.0282    2.8312 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5824   -0.1224    1.4919 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1932   -0.1160    2.8071 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4022   -0.0802   -0.3457 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4279    0.7142   -3.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5182   -1.0589   -3.0577 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5860   -0.9950   -2.4174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7610    0.6408   -2.6597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3411    0.2744   -1.9039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5261    2.5805   -0.7978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4841    0.0010    0.5132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2269   -1.3391    3.6747 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8135   -0.0965    3.5873 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  4  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
  8 19  2  0
 19 20  1  0
 19  2  1  0
 17  9  2  0
  3 21  1  0
  5 22  1  0
  5 23  1  0
  6 24  1  0
 12 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 18 29  1  0
 20 30  1  0
M  END


  Mrv0541 05061307312D          

 20 21  0  0  0  0            999 V2000
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  2  0  0  0  0
  5  3  1  0  0  0  0
  6  2  2  0  0  0  0
  6  4  1  0  0  0  0
  7  1  1  0  0  0  0
  8  2  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  2  0  0  0  0
 12 10  2  0  0  0  0
 12 11  1  0  0  0  0
 13  3  1  0  0  0  0
 14  4  1  0  0  0  0
 15  7  2  0  0  0  0
 16  8  2  0  0  0  0
 17  9  1  0  0  0  0
 18 10  1  0  0  0  0
 19  5  1  0  0  0  0
 19 11  1  0  0  0  0
 20  6  1  0  0  0  0
 20 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034034

> <DATABASE_NAME>
hmdb

> <SMILES>
OCC1=CC(=O)C(O)=C(O1)C1=C(O)C(=O)C=C(CO)O1

> <INCHI_IDENTIFIER>
InChI=1S/C12H10O8/c13-3-5-1-7(15)9(17)11(19-5)12-10(18)8(16)2-6(4-14)20-12/h1-2,13-14,17-18H,3-4H2

> <INCHI_KEY>
SBAWSKBDCSMRPE-UHFFFAOYSA-N

> <FORMULA>
C12H10O8

> <MOLECULAR_WEIGHT>
282.203

> <EXACT_MASS>
282.037567296

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
25.472285027314303

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-hydroxy-2-[3-hydroxy-6-(hydroxymethyl)-4-oxo-4H-pyran-2-yl]-6-(hydroxymethyl)-4H-pyran-4-one

> <ALOGPS_LOGP>
-0.68

> <JCHEM_LOGP>
-1.4819595273333337

> <ALOGPS_LOGS>
-2.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.956821289502566

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.8905326607627195

> <JCHEM_PKA_STRONGEST_BASIC>
-3.085698413237351

> <JCHEM_POLAR_SURFACE_AREA>
133.52

> <JCHEM_REFRACTIVITY>
70.70340000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.29e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-2-[3-hydroxy-6-(hydroxymethyl)-4-oxopyran-2-yl]-6-(hydroxymethyl)pyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034034
     RDKit          3D
Bikojic acid
 30 31  0  0  0  0  0  0  0  0999 V2000
    3.7549   -0.0838    2.1705 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9681   -0.0999    1.2067 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3552   -0.0971   -0.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4306   -0.1156   -1.1258 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8688   -0.1113   -2.5662 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2563   -0.0874   -2.5875 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1805   -0.1367   -0.8003 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7008   -0.1424    0.4634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7477   -0.1630    0.6073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3959    0.2767   -0.4826 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6856    0.3451   -0.5466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4054    0.8396   -1.7729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5962    2.2015   -1.7063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4111   -0.0479    0.5432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8215   -0.5097    1.6928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4441   -0.8800    2.7142 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4109   -0.5628    1.7028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7811   -1.0282    2.8312 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5824   -0.1224    1.4919 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1932   -0.1160    2.8071 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4022   -0.0802   -0.3457 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4279    0.7142   -3.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5182   -1.0589   -3.0577 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5860   -0.9950   -2.4174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7610    0.6408   -2.6597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3411    0.2744   -1.9039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5261    2.5805   -0.7978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4841    0.0010    0.5132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2269   -1.3391    3.6747 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8135   -0.0965    3.5873 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  4  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
  8 19  2  0
 19 20  1  0
 19  2  1  0
 17  9  2  0
  3 21  1  0
  5 22  1  0
  5 23  1  0
  6 24  1  0
 12 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 18 29  1  0
 20 30  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      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -5.335   0.000   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
CONECT    1    5    7                                                       
CONECT    2    6    8                                                       
CONECT    3    5   13                                                       
CONECT    4    6   14                                                       
CONECT    5    1    3   19                                                  
CONECT    6    2    4   20                                                  
CONECT    7    1    9   15                                                  
CONECT    8    2   10   16                                                  
CONECT    9    7   11   17                                                  
CONECT   10    8   12   18                                                  
CONECT   11    9   12   19                                                  
CONECT   12   10   11   20                                                  
CONECT   13    3                                                            
CONECT   14    4                                                            
CONECT   15    7                                                            
CONECT   16    8                                                            
CONECT   17    9                                                            
CONECT   18   10                                                            
CONECT   19    5   11                                                       
CONECT   20    6   12                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0034034
HETATM    1  O1  UNL     1       3.755  -0.084   2.170  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.968  -0.100   1.207  1.00  0.00           C  
HETATM    3  C2  UNL     1       3.355  -0.097  -0.107  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.431  -0.116  -1.126  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.869  -0.111  -2.566  1.00  0.00           C  
HETATM    6  O2  UNL     1       4.256  -0.087  -2.587  1.00  0.00           O  
HETATM    7  O3  UNL     1       1.181  -0.137  -0.800  1.00  0.00           O  
HETATM    8  C5  UNL     1       0.701  -0.142   0.463  1.00  0.00           C  
HETATM    9  C6  UNL     1      -0.748  -0.163   0.607  1.00  0.00           C  
HETATM   10  O4  UNL     1      -1.396   0.277  -0.483  1.00  0.00           O  
HETATM   11  C7  UNL     1      -2.686   0.345  -0.547  1.00  0.00           C  
HETATM   12  C8  UNL     1      -3.405   0.840  -1.773  1.00  0.00           C  
HETATM   13  O5  UNL     1      -3.596   2.202  -1.706  1.00  0.00           O  
HETATM   14  C9  UNL     1      -3.411  -0.048   0.543  1.00  0.00           C  
HETATM   15  C10 UNL     1      -2.821  -0.510   1.693  1.00  0.00           C  
HETATM   16  O6  UNL     1      -3.444  -0.880   2.714  1.00  0.00           O  
HETATM   17  C11 UNL     1      -1.411  -0.563   1.703  1.00  0.00           C  
HETATM   18  O7  UNL     1      -0.781  -1.028   2.831  1.00  0.00           O  
HETATM   19  C12 UNL     1       1.582  -0.122   1.492  1.00  0.00           C  
HETATM   20  O8  UNL     1       1.193  -0.116   2.807  1.00  0.00           O  
HETATM   21  H1  UNL     1       4.402  -0.080  -0.346  1.00  0.00           H  
HETATM   22  H2  UNL     1       2.428   0.714  -3.129  1.00  0.00           H  
HETATM   23  H3  UNL     1       2.518  -1.059  -3.058  1.00  0.00           H  
HETATM   24  H4  UNL     1       4.586  -0.995  -2.417  1.00  0.00           H  
HETATM   25  H5  UNL     1      -2.761   0.641  -2.660  1.00  0.00           H  
HETATM   26  H6  UNL     1      -4.341   0.274  -1.904  1.00  0.00           H  
HETATM   27  H7  UNL     1      -3.526   2.580  -0.798  1.00  0.00           H  
HETATM   28  H8  UNL     1      -4.484   0.001   0.513  1.00  0.00           H  
HETATM   29  H9  UNL     1      -1.227  -1.339   3.675  1.00  0.00           H  
HETATM   30  H10 UNL     1       1.813  -0.096   3.587  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   19
CONECT    3    4    4   21
CONECT    4    5    7
CONECT    5    6   22   23
CONECT    6   24
CONECT    7    8
CONECT    8    9   19   19
CONECT    9   10   17   17
CONECT   10   11
CONECT   11   12   14   14
CONECT   12   13   25   26
CONECT   13   27
CONECT   14   15   28
CONECT   15   16   16   17
CONECT   17   18
CONECT   18   29
CONECT   19   20
CONECT   20   30
END

HMDB0034034
     RDKit          3D
Bikojic acid
 30 31  0  0  0  0  0  0  0  0999 V2000
    3.7549   -0.0838    2.1705 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9681   -0.0999    1.2067 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3552   -0.0971   -0.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4306   -0.1156   -1.1258 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8688   -0.1113   -2.5662 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2563   -0.0874   -2.5875 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1805   -0.1367   -0.8003 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7008   -0.1424    0.4634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7477   -0.1630    0.6073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3959    0.2767   -0.4826 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6856    0.3451   -0.5466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4054    0.8396   -1.7729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5962    2.2015   -1.7063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4111   -0.0479    0.5432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8215   -0.5097    1.6928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4441   -0.8800    2.7142 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4109   -0.5628    1.7028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7811   -1.0282    2.8312 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5824   -0.1224    1.4919 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1932   -0.1160    2.8071 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4022   -0.0802   -0.3457 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4279    0.7142   -3.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5182   -1.0589   -3.0577 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5860   -0.9950   -2.4174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7610    0.6408   -2.6597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3411    0.2744   -1.9039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5261    2.5805   -0.7978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4841    0.0010    0.5132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2269   -1.3391    3.6747 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8135   -0.0965    3.5873 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  4  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
  8 19  2  0
 19 20  1  0
 19  2  1  0
 17  9  2  0
  3 21  1  0
  5 22  1  0
  5 23  1  0
  6 24  1  0
 12 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 18 29  1  0
 20 30  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Bikojate	Generator
BGY-F compound	MeSH
BGY-F	MeSH
6,6'-Bis(5-hydroxy-2-hydroxymethyl-4H-pyran-4-one)	HMDB

Chemical Formula

C₁₂H₁₀O₈

Average Molecular Weight

282.203

Monoisotopic Molecular Weight

282.037567296

IUPAC Name

3-hydroxy-2-[3-hydroxy-6-(hydroxymethyl)-4-oxo-4H-pyran-2-yl]-6-(hydroxymethyl)-4H-pyran-4-one

Traditional Name

3-hydroxy-2-[3-hydroxy-6-(hydroxymethyl)-4-oxopyran-2-yl]-6-(hydroxymethyl)pyran-4-one

CAS Registry Number

Not Available

SMILES

OCC1=CC(=O)C(O)=C(O1)C1=C(O)C(=O)C=C(CO)O1

InChI Identifier

InChI=1S/C12H10O8/c13-3-5-1-7(15)9(17)11(19-5)12-10(18)8(16)2-6(4-14)20-12/h1-2,13-14,17-18H,3-4H2

InChI Key

SBAWSKBDCSMRPE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrans

Sub Class

Pyranones and derivatives

Direct Parent

Pyranones and derivatives

Alternative Parents

Substituents

Pyranone
Heteroaromatic compound
Cyclic ketone
Oxacycle
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic alcohol
Primary alcohol
Organooxygen compound
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0034034)
Cytoplasm (HMDB: HMDB0034034)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034034)

Source

Exogenous

Exogenous (HMDB: HMDB0034034)

Food

Food (HMDB: HMDB0034034)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0034034)

Environmental role

Environmental contaminant (HMDB: HMDB0034034)

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	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.29 g/L	ALOGPS
logP	-0.68	ALOGPS
logP	-1.5	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	7.89	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.52 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	70.7 m³·mol⁻¹	ChemAxon
Polarizability	25.47 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	164.172	31661259
DarkChem	[M-H]-	166.085	31661259
DeepCCS	[M+H]+	166.917	30932474
DeepCCS	[M-H]-	164.521	30932474
DeepCCS	[M-2H]-	197.61	30932474
DeepCCS	[M+Na]+	172.937	30932474
AllCCS	[M+H]+	161.7	32859911
AllCCS	[M+H-H2O]+	157.8	32859911
AllCCS	[M+NH4]+	165.4	32859911
AllCCS	[M+Na]+	166.4	32859911
AllCCS	[M-H]-	158.8	32859911
AllCCS	[M+Na-2H]-	158.5	32859911
AllCCS	[M+HCOO]-	158.3	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.	2.78 minutes	32390414
Predicted by Siyang on May 30, 2022	9.569 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.32 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	69.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	938.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	241.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	71.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	155.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	47.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	260.3 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	262.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	774.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	596.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	141.2 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	1133.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	198.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	192.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	538.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	267.3 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	239.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Bikojic acid	OCC1=CC(=O)C(O)=C(O1)C1=C(O)C(=O)C=C(CO)O1	2763.1	Standard polar	33892256
Bikojic acid	OCC1=CC(=O)C(O)=C(O1)C1=C(O)C(=O)C=C(CO)O1	2352.3	Standard non polar	33892256
Bikojic acid	OCC1=CC(=O)C(O)=C(O1)C1=C(O)C(=O)C=C(CO)O1	2699.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Bikojic acid,1TMS,isomer #1	C[Si](C)(C)OCC1=CC(=O)C(O)=C(C2=C(O)C(=O)C=C(CO)O2)O1	2706.6	Semi standard non polar	33892256
Bikojic acid,1TMS,isomer #2	C[Si](C)(C)OC1=C(C2=C(O)C(=O)C=C(CO)O2)OC(CO)=CC1=O	2642.6	Semi standard non polar	33892256
Bikojic acid,2TMS,isomer #1	C[Si](C)(C)OCC1=CC(=O)C(O[Si](C)(C)C)=C(C2=C(O)C(=O)C=C(CO)O2)O1	2649.0	Semi standard non polar	33892256
Bikojic acid,2TMS,isomer #2	C[Si](C)(C)OCC1=CC(=O)C(O)=C(C2=C(O)C(=O)C=C(CO[Si](C)(C)C)O2)O1	2706.1	Semi standard non polar	33892256
Bikojic acid,2TMS,isomer #3	C[Si](C)(C)OCC1=CC(=O)C(O)=C(C2=C(O[Si](C)(C)C)C(=O)C=C(CO)O2)O1	2641.8	Semi standard non polar	33892256
Bikojic acid,2TMS,isomer #4	C[Si](C)(C)OC1=C(C2=C(O[Si](C)(C)C)C(=O)C=C(CO)O2)OC(CO)=CC1=O	2600.6	Semi standard non polar	33892256
Bikojic acid,3TMS,isomer #1	C[Si](C)(C)OCC1=CC(=O)C(O)=C(C2=C(O[Si](C)(C)C)C(=O)C=C(CO[Si](C)(C)C)O2)O1	2644.2	Semi standard non polar	33892256
Bikojic acid,3TMS,isomer #2	C[Si](C)(C)OCC1=CC(=O)C(O[Si](C)(C)C)=C(C2=C(O[Si](C)(C)C)C(=O)C=C(CO)O2)O1	2593.5	Semi standard non polar	33892256
Bikojic acid,4TMS,isomer #1	C[Si](C)(C)OCC1=CC(=O)C(O[Si](C)(C)C)=C(C2=C(O[Si](C)(C)C)C(=O)C=C(CO[Si](C)(C)C)O2)O1	2650.5	Semi standard non polar	33892256
Bikojic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1=CC(=O)C(O)=C(C2=C(O)C(=O)C=C(CO)O2)O1	2986.7	Semi standard non polar	33892256
Bikojic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=C(C2=C(O)C(=O)C=C(CO)O2)OC(CO)=CC1=O	2939.1	Semi standard non polar	33892256
Bikojic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1=CC(=O)C(O[Si](C)(C)C(C)(C)C)=C(C2=C(O)C(=O)C=C(CO)O2)O1	3159.7	Semi standard non polar	33892256
Bikojic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC1=CC(=O)C(O)=C(C2=C(O)C(=O)C=C(CO[Si](C)(C)C(C)(C)C)O2)O1	3205.9	Semi standard non polar	33892256
Bikojic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OCC1=CC(=O)C(O)=C(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C=C(CO)O2)O1	3158.8	Semi standard non polar	33892256
Bikojic acid,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=C(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C=C(CO)O2)OC(CO)=CC1=O	3120.1	Semi standard non polar	33892256
Bikojic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1=CC(=O)C(O)=C(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C=C(CO[Si](C)(C)C(C)(C)C)O2)O1	3378.9	Semi standard non polar	33892256
Bikojic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC1=CC(=O)C(O[Si](C)(C)C(C)(C)C)=C(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C=C(CO)O2)O1	3350.9	Semi standard non polar	33892256
Bikojic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1=CC(=O)C(O[Si](C)(C)C(C)(C)C)=C(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C=C(CO[Si](C)(C)C(C)(C)C)O2)O1	3540.5	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 - Bikojic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0w29-2190000000-45a407fb847579601b2a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bikojic acid GC-MS (4 TMS) - 70eV, Positive	splash10-0a4i-6000390000-574f14a3625962f688ec	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bikojic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bikojic acid 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 - Bikojic acid 10V, Positive-QTOF	splash10-001i-0090000000-231d9e5d2a0de5546269	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bikojic acid 20V, Positive-QTOF	splash10-00lr-0290000000-c2bd3776c461789ea17a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bikojic acid 40V, Positive-QTOF	splash10-052e-9730000000-98611cf1b301e12c2f62	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bikojic acid 10V, Negative-QTOF	splash10-001i-0590000000-41cd563447b5210e759a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bikojic acid 20V, Negative-QTOF	splash10-0f6x-5590000000-daa9ae3c17ea6b6847d1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bikojic acid 40V, Negative-QTOF	splash10-059x-9100000000-029b512c04c04673fe3b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bikojic acid 10V, Positive-QTOF	splash10-00lr-0090000000-e4e9a07351fe0d42e995	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bikojic acid 20V, Positive-QTOF	splash10-000i-0290000000-29fadd54085b1ffad920	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bikojic acid 40V, Positive-QTOF	splash10-05fr-2890000000-667910f92241aa1008dd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bikojic acid 10V, Negative-QTOF	splash10-001i-0090000000-f93d2f26ed6dd718ec66	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bikojic acid 20V, Negative-QTOF	splash10-0gx0-0290000000-2ed13b21194b709e2d41	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bikojic acid 40V, Negative-QTOF	splash10-0knc-8890000000-4452c8ef3090a02feb83	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB012274

KNApSAcK ID

Not Available

Chemspider ID

30777040

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

89014314

PDB ID

Not Available

ChEBI ID

174676

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

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 Bikojic acid (HMDB0034034)

MOL for HMDB0034034 (Bikojic acid)

3D MOL for HMDB0034034 (Bikojic acid)

3D SDF for HMDB0034034 (Bikojic acid)

3D-SDF for HMDB0034034 (Bikojic acid)

PDB for HMDB0034034 (Bikojic acid)

3D PDB for HMDB0034034 (Bikojic acid)

SMILES for HMDB0034034 (Bikojic acid)

INCHI for HMDB0034034 (Bikojic acid)

Structure for HMDB0034034 (Bikojic acid)

3D Structure for HMDB0034034 (Bikojic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra