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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:51:15 UTC

Update Date

2022-03-07 02:53:26 UTC

HMDB ID

HMDB0032695

Secondary Accession Numbers

HMDB32695

Metabolite Identification

Common Name

Barpisoflavone A

Description

Barpisoflavone A belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom. Barpisoflavone A has been detected, but not quantified in, scarlet beans (Phaseolus coccineus). This could make barpisoflavone a a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Barpisoflavone A.

Structure

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

HMDB0032695
     RDKit          3D
Barpisoflavone A
 34 36  0  0  0  0  0  0  0  0999 V2000
   -3.3037   -2.8032   -0.3634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3941   -1.7794   -0.1684 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6634   -0.4575    0.1080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9047    0.0959    0.2626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0654    1.4463    0.5454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3480    1.9498    0.6913 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9569    2.2516    0.6739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6875    1.7250    0.5230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6056    2.4830    0.6403 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6107    2.0070    0.4982 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8397    0.6812    0.2168 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1632    0.0982    0.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4946   -1.0962    0.6739 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7396   -1.6251    0.4879 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7101   -1.0317   -0.3100 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9709   -1.6002   -0.4773 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3365    0.1510   -0.9190 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0929    0.7224   -0.7613 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7796    1.9095   -1.3987 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2833   -0.1137    0.0950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1329   -1.3233   -0.1574 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5556    0.3940    0.2456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3329   -2.4583   -0.1649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0908   -3.7024    0.2827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2662   -3.1709   -1.4202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7697   -0.5369    0.1594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8348    2.3099   -0.1234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0492    3.3171    0.8978 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4598    2.6694    0.6048 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7314   -1.5520    1.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9951   -2.5665    0.9906 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7409   -1.3712    0.1399 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1006    0.6229   -1.5532 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4789    2.3543   -1.9878 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 11 20  1  0
 20 21  2  0
 20 22  1  0
 22  3  1  0
 22  8  2  0
 18 12  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
 10 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  0
 17 33  1  0
 19 34  1  0
M  END


  Mrv0541 05061306382D          

 22 24  0  0  0  0            999 V2000
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    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    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    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
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    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
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    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
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  8  2  1  0  0  0  0
  8  4  2  0  0  0  0
  9  5  2  0  0  0  0
  9  6  1  0  0  0  0
 10  3  1  0  0  0  0
 11  7  2  0  0  0  0
 11 10  1  0  0  0  0
 12  4  1  0  0  0  0
 12 10  2  0  0  0  0
 13  5  1  0  0  0  0
 14  6  2  0  0  0  0
 15 13  2  0  0  0  0
 15 14  1  0  0  0  0
 16 11  1  0  0  0  0
 16 15  1  0  0  0  0
 17  8  1  0  0  0  0
 18  9  1  0  0  0  0
 19 12  1  0  0  0  0
 20 16  2  0  0  0  0
 21  1  1  0  0  0  0
 21 13  1  0  0  0  0
 22  7  1  0  0  0  0
 22 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032695

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C2C(=O)C(=COC2=CC(O)=C1)C1=C(O)C=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O6/c1-21-13-5-9(18)6-14-15(13)16(20)11(7-22-14)10-3-2-8(17)4-12(10)19/h2-7,17-19H,1H3

> <INCHI_KEY>
TUTSVLUUGMNALO-UHFFFAOYSA-N

> <FORMULA>
C16H12O6

> <MOLECULAR_WEIGHT>
300.2629

> <EXACT_MASS>
300.063388116

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
29.33163592879754

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(2,4-dihydroxyphenyl)-7-hydroxy-5-methoxy-4H-chromen-4-one

> <ALOGPS_LOGP>
3.01

> <JCHEM_LOGP>
2.2692011239999994

> <ALOGPS_LOGS>
-3.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.519283424358903

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.534457145983495

> <JCHEM_PKA_STRONGEST_BASIC>
-4.766630310903108

> <JCHEM_POLAR_SURFACE_AREA>
96.22

> <JCHEM_REFRACTIVITY>
78.1461

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.80e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(2,4-dihydroxyphenyl)-7-hydroxy-5-methoxychromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0032695
     RDKit          3D
Barpisoflavone A
 34 36  0  0  0  0  0  0  0  0999 V2000
   -3.3037   -2.8032   -0.3634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3941   -1.7794   -0.1684 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6634   -0.4575    0.1080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9047    0.0959    0.2626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0654    1.4463    0.5454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3480    1.9498    0.6913 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9569    2.2516    0.6739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6875    1.7250    0.5230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6056    2.4830    0.6403 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6107    2.0070    0.4982 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8397    0.6812    0.2168 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1632    0.0982    0.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4946   -1.0962    0.6739 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7396   -1.6251    0.4879 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7101   -1.0317   -0.3100 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9709   -1.6002   -0.4773 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3365    0.1510   -0.9190 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0929    0.7224   -0.7613 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7796    1.9095   -1.3987 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2833   -0.1137    0.0950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1329   -1.3233   -0.1574 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5556    0.3940    0.2456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3329   -2.4583   -0.1649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0908   -3.7024    0.2827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2662   -3.1709   -1.4202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7697   -0.5369    0.1594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8348    2.3099   -0.1234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0492    3.3171    0.8978 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4598    2.6694    0.6048 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7314   -1.5520    1.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9951   -2.5665    0.9906 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7409   -1.3712    0.1399 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1006    0.6229   -1.5532 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4789    2.3543   -1.9878 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 11 20  1  0
 20 21  2  0
 20 22  1  0
 22  3  1  0
 22  8  2  0
 18 12  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
 10 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  0
 17 33  1  0
 19 34  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   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      12.003   6.930   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2    3    8                                                       
CONECT    3    2   10                                                       
CONECT    4    8   12                                                       
CONECT    5    9   13                                                       
CONECT    6    9   14                                                       
CONECT    7   11   22                                                       
CONECT    8    2    4   17                                                  
CONECT    9    5    6   18                                                  
CONECT   10    3   11   12                                                  
CONECT   11    7   10   16                                                  
CONECT   12    4   10   19                                                  
CONECT   13    5   15   21                                                  
CONECT   14    6   15   22                                                  
CONECT   15   13   14   16                                                  
CONECT   16   11   15   20                                                  
CONECT   17    8                                                            
CONECT   18    9                                                            
CONECT   19   12                                                            
CONECT   20   16                                                            
CONECT   21    1   13                                                       
CONECT   22    7   14                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0032695
HETATM    1  C1  UNL     1      -3.304  -2.803  -0.363  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.394  -1.779  -0.168  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.663  -0.458   0.108  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.905   0.096   0.263  1.00  0.00           C  
HETATM    5  C4  UNL     1      -4.065   1.446   0.545  1.00  0.00           C  
HETATM    6  O2  UNL     1      -5.348   1.950   0.691  1.00  0.00           O  
HETATM    7  C5  UNL     1      -2.957   2.252   0.674  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.687   1.725   0.523  1.00  0.00           C  
HETATM    9  O3  UNL     1      -0.606   2.483   0.640  1.00  0.00           O  
HETATM   10  C7  UNL     1       0.611   2.007   0.498  1.00  0.00           C  
HETATM   11  C8  UNL     1       0.840   0.681   0.217  1.00  0.00           C  
HETATM   12  C9  UNL     1       2.163   0.098   0.039  1.00  0.00           C  
HETATM   13  C10 UNL     1       2.495  -1.096   0.674  1.00  0.00           C  
HETATM   14  C11 UNL     1       3.740  -1.625   0.488  1.00  0.00           C  
HETATM   15  C12 UNL     1       4.710  -1.032  -0.310  1.00  0.00           C  
HETATM   16  O4  UNL     1       5.971  -1.600  -0.477  1.00  0.00           O  
HETATM   17  C13 UNL     1       4.337   0.151  -0.919  1.00  0.00           C  
HETATM   18  C14 UNL     1       3.093   0.722  -0.761  1.00  0.00           C  
HETATM   19  O5  UNL     1       2.780   1.909  -1.399  1.00  0.00           O  
HETATM   20  C15 UNL     1      -0.283  -0.114   0.095  1.00  0.00           C  
HETATM   21  O6  UNL     1      -0.133  -1.323  -0.157  1.00  0.00           O  
HETATM   22  C16 UNL     1      -1.556   0.394   0.246  1.00  0.00           C  
HETATM   23  H1  UNL     1      -4.333  -2.458  -0.165  1.00  0.00           H  
HETATM   24  H2  UNL     1      -3.091  -3.702   0.283  1.00  0.00           H  
HETATM   25  H3  UNL     1      -3.266  -3.171  -1.420  1.00  0.00           H  
HETATM   26  H4  UNL     1      -4.770  -0.537   0.159  1.00  0.00           H  
HETATM   27  H5  UNL     1      -5.835   2.310  -0.123  1.00  0.00           H  
HETATM   28  H6  UNL     1      -3.049   3.317   0.898  1.00  0.00           H  
HETATM   29  H7  UNL     1       1.460   2.669   0.605  1.00  0.00           H  
HETATM   30  H8  UNL     1       1.731  -1.552   1.295  1.00  0.00           H  
HETATM   31  H9  UNL     1       3.995  -2.567   0.991  1.00  0.00           H  
HETATM   32  H10 UNL     1       6.741  -1.371   0.140  1.00  0.00           H  
HETATM   33  H11 UNL     1       5.101   0.623  -1.553  1.00  0.00           H  
HETATM   34  H12 UNL     1       3.479   2.354  -1.988  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4   22
CONECT    4    5   26
CONECT    5    6    7    7
CONECT    6   27
CONECT    7    8   28
CONECT    8    9   22   22
CONECT    9   10
CONECT   10   11   11   29
CONECT   11   12   20
CONECT   12   13   13   18
CONECT   13   14   30
CONECT   14   15   15   31
CONECT   15   16   17
CONECT   16   32
CONECT   17   18   18   33
CONECT   18   19
CONECT   19   34
CONECT   20   21   21   22
END

HMDB0032695
     RDKit          3D
Barpisoflavone A
 34 36  0  0  0  0  0  0  0  0999 V2000
   -3.3037   -2.8032   -0.3634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3941   -1.7794   -0.1684 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6634   -0.4575    0.1080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9047    0.0959    0.2626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0654    1.4463    0.5454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3480    1.9498    0.6913 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9569    2.2516    0.6739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6875    1.7250    0.5230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6056    2.4830    0.6403 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6107    2.0070    0.4982 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8397    0.6812    0.2168 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1632    0.0982    0.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4946   -1.0962    0.6739 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7396   -1.6251    0.4879 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7101   -1.0317   -0.3100 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9709   -1.6002   -0.4773 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3365    0.1510   -0.9190 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0929    0.7224   -0.7613 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7796    1.9095   -1.3987 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2833   -0.1137    0.0950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1329   -1.3233   -0.1574 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5556    0.3940    0.2456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3329   -2.4583   -0.1649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0908   -3.7024    0.2827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2662   -3.1709   -1.4202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7697   -0.5369    0.1594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8348    2.3099   -0.1234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0492    3.3171    0.8978 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4598    2.6694    0.6048 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7314   -1.5520    1.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9951   -2.5665    0.9906 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7409   -1.3712    0.1399 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1006    0.6229   -1.5532 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4789    2.3543   -1.9878 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 11 20  1  0
 20 21  2  0
 20 22  1  0
 22  3  1  0
 22  8  2  0
 18 12  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
 10 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  0
 17 33  1  0
 19 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2',4',7-Trihydroxy-5-methoxyisoflavone	HMDB
2'-Hydroxyisoprunetin	HMDB

Chemical Formula

C₁₆H₁₂O₆

Average Molecular Weight

300.2629

Monoisotopic Molecular Weight

300.063388116

IUPAC Name

3-(2,4-dihydroxyphenyl)-7-hydroxy-5-methoxy-4H-chromen-4-one

Traditional Name

3-(2,4-dihydroxyphenyl)-7-hydroxy-5-methoxychromen-4-one

CAS Registry Number

101691-27-4

SMILES

COC1=C2C(=O)C(=COC2=CC(O)=C1)C1=C(O)C=C(O)C=C1

InChI Identifier

InChI=1S/C16H12O6/c1-21-13-5-9(18)6-14-15(13)16(20)11(7-22-14)10-3-2-8(17)4-12(10)19/h2-7,17-19H,1H3

InChI Key

TUTSVLUUGMNALO-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflav-2-enes

Direct Parent

Isoflavones

Alternative Parents

Substituents

Hydroxyisoflavonoid
Isoflavone
Chromone
Benzopyran
1-benzopyran
Anisole
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Pyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous ester
Organoheterocyclic compound
Ether
Oxacycle
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0032695)
Cell membrane (HMDB: HMDB0032695)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032695)

Source

Endogenous

Endogenous (HMDB: HMDB0032695)

Plant

Plant (HMDB: HMDB0032695)
Fabaceae (HMDB: HMDB0032695)

Exogenous

Food

Food (HMDB: HMDB0032695)

Pulse

Bean

Scarlet bean (FooDB: FOOD00132)

Exogenous (HMDB: HMDB0032695)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	290 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	680.5 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	0.078 g/L	ALOGPS
logP	3.01	ALOGPS
logP	2.27	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	6.53	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	78.15 m³·mol⁻¹	ChemAxon
Polarizability	29.33 Å³	ChemAxon
Number of Rings	3	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]+	170.841	31661259
DarkChem	[M-H]-	171.461	31661259
DeepCCS	[M+H]+	175.759	30932474
DeepCCS	[M-H]-	173.401	30932474
DeepCCS	[M-2H]-	207.551	30932474
DeepCCS	[M+Na]+	182.777	30932474
AllCCS	[M+H]+	168.0	32859911
AllCCS	[M+H-H2O]+	164.3	32859911
AllCCS	[M+NH4]+	171.4	32859911
AllCCS	[M+Na]+	172.4	32859911
AllCCS	[M-H]-	168.6	32859911
AllCCS	[M+Na-2H]-	167.8	32859911
AllCCS	[M+HCOO]-	167.1	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.	6.83 minutes	32390414
Predicted by Siyang on May 30, 2022	11.0438 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.41 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1701.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	257.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	129.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	162.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	252.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	524.8 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	418.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	273.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	790.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	343.4 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	1316.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	308.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	323.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	451.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	311.2 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	117.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Barpisoflavone A	COC1=C2C(=O)C(=COC2=CC(O)=C1)C1=C(O)C=C(O)C=C1	4577.1	Standard polar	33892256
Barpisoflavone A	COC1=C2C(=O)C(=COC2=CC(O)=C1)C1=C(O)C=C(O)C=C1	2794.6	Standard non polar	33892256
Barpisoflavone A	COC1=C2C(=O)C(=COC2=CC(O)=C1)C1=C(O)C=C(O)C=C1	3166.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Barpisoflavone A,1TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=CC2=C1C(=O)C(C1=CC=C(O)C=C1O)=CO2	3085.4	Semi standard non polar	33892256
Barpisoflavone A,1TMS,isomer #2	COC1=CC(O)=CC2=C1C(=O)C(C1=CC=C(O)C=C1O[Si](C)(C)C)=CO2	3011.6	Semi standard non polar	33892256
Barpisoflavone A,1TMS,isomer #3	COC1=CC(O)=CC2=C1C(=O)C(C1=CC=C(O[Si](C)(C)C)C=C1O)=CO2	3059.8	Semi standard non polar	33892256
Barpisoflavone A,2TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=CC2=C1C(=O)C(C1=CC=C(O[Si](C)(C)C)C=C1O)=CO2	2950.8	Semi standard non polar	33892256
Barpisoflavone A,2TMS,isomer #2	COC1=CC(O[Si](C)(C)C)=CC2=C1C(=O)C(C1=CC=C(O)C=C1O[Si](C)(C)C)=CO2	2941.9	Semi standard non polar	33892256
Barpisoflavone A,2TMS,isomer #3	COC1=CC(O)=CC2=C1C(=O)C(C1=CC=C(O[Si](C)(C)C)C=C1O[Si](C)(C)C)=CO2	2958.3	Semi standard non polar	33892256
Barpisoflavone A,3TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=CC2=C1C(=O)C(C1=CC=C(O[Si](C)(C)C)C=C1O[Si](C)(C)C)=CO2	2895.9	Semi standard non polar	33892256
Barpisoflavone A,1TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=CC2=C1C(=O)C(C1=CC=C(O)C=C1O)=CO2	3358.8	Semi standard non polar	33892256
Barpisoflavone A,1TBDMS,isomer #2	COC1=CC(O)=CC2=C1C(=O)C(C1=CC=C(O)C=C1O[Si](C)(C)C(C)(C)C)=CO2	3287.0	Semi standard non polar	33892256
Barpisoflavone A,1TBDMS,isomer #3	COC1=CC(O)=CC2=C1C(=O)C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O)=CO2	3334.8	Semi standard non polar	33892256
Barpisoflavone A,2TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=CC2=C1C(=O)C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O)=CO2	3482.9	Semi standard non polar	33892256
Barpisoflavone A,2TBDMS,isomer #2	COC1=CC(O[Si](C)(C)C(C)(C)C)=CC2=C1C(=O)C(C1=CC=C(O)C=C1O[Si](C)(C)C(C)(C)C)=CO2	3440.0	Semi standard non polar	33892256
Barpisoflavone A,2TBDMS,isomer #3	COC1=CC(O)=CC2=C1C(=O)C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C)=CO2	3446.6	Semi standard non polar	33892256
Barpisoflavone A,3TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=CC2=C1C(=O)C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C)=CO2	3586.4	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 - Barpisoflavone A GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-0691000000-f9a8e0f71d8edd9cfaff	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Barpisoflavone A GC-MS (3 TMS) - 70eV, Positive	splash10-0ukc-1080950000-b7d2f8a771fc41478884	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Barpisoflavone A 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Barpisoflavone A , positive-QTOF	splash10-0udi-0879000000-013b69dda9969194e44e	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Barpisoflavone A 10V, Positive-QTOF	splash10-0udi-0009000000-6c20d40d8c15430db8e6	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Barpisoflavone A 20V, Positive-QTOF	splash10-0udi-0029000000-ea58d3806b6c40f22f5b	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Barpisoflavone A 40V, Positive-QTOF	splash10-0gb9-2790000000-a91c1721f47662aade15	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Barpisoflavone A 10V, Negative-QTOF	splash10-0002-0090000000-df454de542410197829c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Barpisoflavone A 20V, Negative-QTOF	splash10-0002-0090000000-fb5cd300639f4f2f9e36	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Barpisoflavone A 40V, Negative-QTOF	splash10-067i-3970000000-92224ab1c64683ade411	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Barpisoflavone A 10V, Positive-QTOF	splash10-0udi-0009000000-545fc7c692e0abcd7966	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Barpisoflavone A 20V, Positive-QTOF	splash10-0udi-0009000000-6a27502587726ed7fc95	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Barpisoflavone A 40V, Positive-QTOF	splash10-0560-0490000000-14271fc4dd6d16c92327	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Barpisoflavone A 10V, Negative-QTOF	splash10-0002-0090000000-fb4a565723d52a1e4624	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Barpisoflavone A 20V, Negative-QTOF	splash10-0002-0090000000-7822d96b278917a6a0bf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Barpisoflavone A 40V, Negative-QTOF	splash10-004i-0490000000-499ce5d8d1c68b37580a	2021-09-22	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

FDB010652

KNApSAcK ID

C00020291

Chemspider ID

8119755

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9944143

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1830951

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

Barpisoflavone A → 3,4,5-trihydroxy-6-[3-hydroxy-4-(7-hydroxy-5-methoxy-4-oxo-4H-chromen-3-yl)phenoxy]oxane-2-carboxylic acid	details
Barpisoflavone A → 6-{[3-(2,4-dihydroxyphenyl)-5-methoxy-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid	details

Showing metabocard for Barpisoflavone A (HMDB0032695)

MOL for HMDB0032695 (Barpisoflavone A)

3D MOL for HMDB0032695 (Barpisoflavone A)

3D SDF for HMDB0032695 (Barpisoflavone A)

3D-SDF for HMDB0032695 (Barpisoflavone A)

PDB for HMDB0032695 (Barpisoflavone A)

3D PDB for HMDB0032695 (Barpisoflavone A)

SMILES for HMDB0032695 (Barpisoflavone A)

INCHI for HMDB0032695 (Barpisoflavone A)

Structure for HMDB0032695 (Barpisoflavone A)

3D Structure for HMDB0032695 (Barpisoflavone A)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions