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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:42:51 UTC

Update Date

2022-03-07 02:53:54 UTC

HMDB ID

HMDB0033940

Secondary Accession Numbers

HMDB33940

Metabolite Identification

Common Name

Vignafuran

Description

Vignafuran belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. Thus, vignafuran is considered to be a flavonoid. Vignafuran has been detected, but not quantified in, a few different foods, such as cowpeas (Vigna unguiculata), hyacinth beans (Lablab purpureus), and pulses. This could make vignafuran a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Vignafuran.

Structure

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

HMDB0033940
     RDKit          3D
Vignafuran
 34 36  0  0  0  0  0  0  0  0999 V2000
    5.9129    1.2915   -0.3863 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5506   -0.0187    0.0168 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2133   -0.3412    0.1182 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8624   -1.6078    0.5079 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5414   -1.9683    0.6208 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5692   -1.0404    0.3374 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1640   -1.0582    0.3452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3016    0.1700   -0.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6871    0.6018   -0.1618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9591    1.9139   -0.5644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2373    2.4029   -0.7126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2836    1.5469   -0.4478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5798    2.0045   -0.5863 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0263    0.2568   -0.0519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7324   -0.2421    0.0992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5590   -1.5580    0.5033 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6379   -2.4232    0.7709 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7693    0.9133   -0.2615 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8782    0.2374   -0.0557 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2234    0.5654   -0.1587 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0136    1.4452   -0.2284 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3435    1.9942    0.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6319    1.5052   -1.4391 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6137   -2.3608    0.7380 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2441   -2.9774    0.9314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3704   -1.9449    0.6185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1452    2.6056   -0.7783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4141    3.4395   -1.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3669    1.3905   -0.3964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8288   -0.4382    0.1629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2351   -2.5978   -0.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3342   -3.4055    1.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3103   -1.8885    1.4996 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4774    1.5865   -0.4728 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
  8 18  1  0
 18 19  1  0
 19 20  2  0
 20  3  1  0
 19  6  1  0
 15  9  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  5 25  1  0
  7 26  1  0
 10 27  1  0
 11 28  1  0
 13 29  1  0
 14 30  1  0
 17 31  1  0
 17 32  1  0
 17 33  1  0
 20 34  1  0
M  END


  Mrv0541 05061307272D          

 20 22  0  0  0  0            999 V2000
    3.4990    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    2.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1034    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9284    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    2.9519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  2  0  0  0  0
  6  4  2  0  0  0  0
 10  3  1  0  0  0  0
 10  7  1  0  0  0  0
 11  4  1  0  0  0  0
 11  8  2  0  0  0  0
 12  5  1  0  0  0  0
 12  9  2  0  0  0  0
 13  6  1  0  0  0  0
 14  9  1  0  0  0  0
 14 10  2  0  0  0  0
 15  8  1  0  0  0  0
 15 13  2  0  0  0  0
 16  7  2  0  0  0  0
 16 13  1  0  0  0  0
 17 11  1  0  0  0  0
 18  1  1  0  0  0  0
 18 12  1  0  0  0  0
 19  2  1  0  0  0  0
 19 15  1  0  0  0  0
 20 14  1  0  0  0  0
 20 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033940

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(C=C(O2)C2=C(OC)C=C(O)C=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O4/c1-18-12-5-3-10-7-16(20-14(10)9-12)13-6-4-11(17)8-15(13)19-2/h3-9,17H,1-2H3

> <INCHI_KEY>
YCDZKMJZSGRQML-UHFFFAOYSA-N

> <FORMULA>
C16H14O4

> <MOLECULAR_WEIGHT>
270.28

> <EXACT_MASS>
270.089208936

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
28.926025755335644

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-methoxy-4-(6-methoxy-1-benzofuran-2-yl)phenol

> <ALOGPS_LOGP>
3.75

> <JCHEM_LOGP>
3.0806878493333327

> <ALOGPS_LOGS>
-3.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.015858325429045

> <JCHEM_PKA_STRONGEST_BASIC>
-3.119930172802826

> <JCHEM_POLAR_SURFACE_AREA>
51.83

> <JCHEM_REFRACTIVITY>
74.82010000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.97e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
vignafuran

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033940
     RDKit          3D
Vignafuran
 34 36  0  0  0  0  0  0  0  0999 V2000
    5.9129    1.2915   -0.3863 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5506   -0.0187    0.0168 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2133   -0.3412    0.1182 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8624   -1.6078    0.5079 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5414   -1.9683    0.6208 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5692   -1.0404    0.3374 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1640   -1.0582    0.3452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3016    0.1700   -0.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6871    0.6018   -0.1618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9591    1.9139   -0.5644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2373    2.4029   -0.7126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2836    1.5469   -0.4478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5798    2.0045   -0.5863 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0263    0.2568   -0.0519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7324   -0.2421    0.0992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5590   -1.5580    0.5033 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6379   -2.4232    0.7709 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7693    0.9133   -0.2615 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8782    0.2374   -0.0557 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2234    0.5654   -0.1587 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0136    1.4452   -0.2284 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3435    1.9942    0.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6319    1.5052   -1.4391 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6137   -2.3608    0.7380 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2441   -2.9774    0.9314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3704   -1.9449    0.6185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1452    2.6056   -0.7783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4141    3.4395   -1.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3669    1.3905   -0.3964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8288   -0.4382    0.1629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2351   -2.5978   -0.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3342   -3.4055    1.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3103   -1.8885    1.4996 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4774    1.5865   -0.4728 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
  8 18  1  0
 18 19  1  0
 19 20  2  0
 20  3  1  0
 19  6  1  0
 15  9  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  5 25  1  0
  7 26  1  0
 10 27  1  0
 11 28  1  0
 13 29  1  0
 14 30  1  0
 17 31  1  0
 17 32  1  0
 17 33  1  0
 20 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       6.531   3.613   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.173   5.510   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.023   1.509   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.483   1.509   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.268   1.597   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.023   4.176   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.793   2.843   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.713   2.843   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.483   4.176   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -7.333   2.843   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.198   4.383   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -2.713   5.510   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -0.268   4.089   0.000  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2   19                                                            
CONECT    3    5   10                                                       
CONECT    4    6   11                                                       
CONECT    5    3   12                                                       
CONECT    6    4   13                                                       
CONECT    7   10   16                                                       
CONECT    8   11   15                                                       
CONECT    9   12   14                                                       
CONECT   10    3    7   14                                                  
CONECT   11    4    8   17                                                  
CONECT   12    5    9   18                                                  
CONECT   13    6   15   16                                                  
CONECT   14    9   10   20                                                  
CONECT   15    8   13   19                                                  
CONECT   16    7   13   20                                                  
CONECT   17   11                                                            
CONECT   18    1   12                                                       
CONECT   19    2   15                                                       
CONECT   20   14   16                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0033940
HETATM    1  C1  UNL     1       5.913   1.292  -0.386  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.551  -0.019   0.017  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.213  -0.341   0.118  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.862  -1.608   0.508  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.541  -1.968   0.621  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.569  -1.040   0.337  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.164  -1.058   0.345  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.302   0.170  -0.031  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.687   0.602  -0.162  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.959   1.914  -0.564  1.00  0.00           C  
HETATM   11  C10 UNL     1      -3.237   2.403  -0.713  1.00  0.00           C  
HETATM   12  C11 UNL     1      -4.284   1.547  -0.448  1.00  0.00           C  
HETATM   13  O2  UNL     1      -5.580   2.004  -0.586  1.00  0.00           O  
HETATM   14  C12 UNL     1      -4.026   0.257  -0.052  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.732  -0.242   0.099  1.00  0.00           C  
HETATM   16  O3  UNL     1      -2.559  -1.558   0.503  1.00  0.00           O  
HETATM   17  C14 UNL     1      -3.638  -2.423   0.771  1.00  0.00           C  
HETATM   18  O4  UNL     1       0.769   0.913  -0.262  1.00  0.00           O  
HETATM   19  C15 UNL     1       1.878   0.237  -0.056  1.00  0.00           C  
HETATM   20  C16 UNL     1       3.223   0.565  -0.159  1.00  0.00           C  
HETATM   21  H1  UNL     1       7.014   1.445  -0.228  1.00  0.00           H  
HETATM   22  H2  UNL     1       5.344   1.994   0.279  1.00  0.00           H  
HETATM   23  H3  UNL     1       5.632   1.505  -1.439  1.00  0.00           H  
HETATM   24  H4  UNL     1       4.614  -2.361   0.738  1.00  0.00           H  
HETATM   25  H5  UNL     1       2.244  -2.977   0.931  1.00  0.00           H  
HETATM   26  H6  UNL     1      -0.370  -1.945   0.618  1.00  0.00           H  
HETATM   27  H7  UNL     1      -1.145   2.606  -0.778  1.00  0.00           H  
HETATM   28  H8  UNL     1      -3.414   3.439  -1.031  1.00  0.00           H  
HETATM   29  H9  UNL     1      -6.367   1.390  -0.396  1.00  0.00           H  
HETATM   30  H10 UNL     1      -4.829  -0.438   0.163  1.00  0.00           H  
HETATM   31  H11 UNL     1      -4.235  -2.598  -0.170  1.00  0.00           H  
HETATM   32  H12 UNL     1      -3.334  -3.405   1.128  1.00  0.00           H  
HETATM   33  H13 UNL     1      -4.310  -1.889   1.500  1.00  0.00           H  
HETATM   34  H14 UNL     1       3.477   1.586  -0.473  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3
CONECT    3    4    4   20
CONECT    4    5   24
CONECT    5    6    6   25
CONECT    6    7   19
CONECT    7    8    8   26
CONECT    8    9   18
CONECT    9   10   10   15
CONECT   10   11   27
CONECT   11   12   12   28
CONECT   12   13   14
CONECT   13   29
CONECT   14   15   15   30
CONECT   15   16
CONECT   16   17
CONECT   17   31   32   33
CONECT   18   19
CONECT   19   20   20
CONECT   20   34
END

HMDB0033940
     RDKit          3D
Vignafuran
 34 36  0  0  0  0  0  0  0  0999 V2000
    5.9129    1.2915   -0.3863 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5506   -0.0187    0.0168 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2133   -0.3412    0.1182 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8624   -1.6078    0.5079 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5414   -1.9683    0.6208 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5692   -1.0404    0.3374 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1640   -1.0582    0.3452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3016    0.1700   -0.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6871    0.6018   -0.1618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9591    1.9139   -0.5644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2373    2.4029   -0.7126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2836    1.5469   -0.4478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5798    2.0045   -0.5863 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0263    0.2568   -0.0519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7324   -0.2421    0.0992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5590   -1.5580    0.5033 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6379   -2.4232    0.7709 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7693    0.9133   -0.2615 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8782    0.2374   -0.0557 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2234    0.5654   -0.1587 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0136    1.4452   -0.2284 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3435    1.9942    0.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6319    1.5052   -1.4391 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6137   -2.3608    0.7380 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2441   -2.9774    0.9314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3704   -1.9449    0.6185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1452    2.6056   -0.7783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4141    3.4395   -1.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3669    1.3905   -0.3964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8288   -0.4382    0.1629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2351   -2.5978   -0.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3342   -3.4055    1.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3103   -1.8885    1.4996 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4774    1.5865   -0.4728 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
  8 18  1  0
 18 19  1  0
 19 20  2  0
 20  3  1  0
 19  6  1  0
 15  9  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  5 25  1  0
  7 26  1  0
 10 27  1  0
 11 28  1  0
 13 29  1  0
 14 30  1  0
 17 31  1  0
 17 32  1  0
 17 33  1  0
 20 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(4-Hydroxy-2-methoxyphenyl)-6-methoxybenzofuran	HMDB

Chemical Formula

C₁₆H₁₄O₄

Average Molecular Weight

270.28

Monoisotopic Molecular Weight

270.089208936

IUPAC Name

3-methoxy-4-(6-methoxy-1-benzofuran-2-yl)phenol

Traditional Name

vignafuran

CAS Registry Number

57800-41-6

SMILES

COC1=CC2=C(C=C(O2)C2=C(OC)C=C(O)C=C2)C=C1

InChI Identifier

InChI=1S/C16H14O4/c1-18-12-5-3-10-7-16(20-14(10)9-12)13-6-4-11(17)8-15(13)19-2/h3-9,17H,1-2H3

InChI Key

YCDZKMJZSGRQML-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

2-arylbenzofuran flavonoids

Sub Class

Not Available

Direct Parent

2-arylbenzofuran flavonoids

Alternative Parents

Substituents

2-arylbenzofuran flavonoid
2-phenylbenzofuran
Phenylbenzofuran
Methoxyphenol
Benzofuran
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Furan
Ether
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

1-benzofurans (CHEBI:9980 )
Other Flavonoids (C08993 )
2-Arylbenzofurans (C08993 )
Other Flavonoids (LMPK12160036 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0033940)
Cell membrane (HMDB: HMDB0033940)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033940)

Source

Exogenous

Exogenous (HMDB: HMDB0033940)

Food

Food (HMDB: HMDB0033940)

Pulse

Pea

Cowpea (FooDB: FOOD00202)

Bean

Hyacinth bean (FooDB: FOOD00381)

Pulses (FooDB: FOOD00867)

Endogenous

Plant

Fabaceae (HMDB: HMDB0033940)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033940)

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	27.39 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	0.05 g/L	ALOGPS
logP	3.75	ALOGPS
logP	3.08	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	9.02	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	51.83 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	74.82 m³·mol⁻¹	ChemAxon
Polarizability	28.93 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]+	163.357	31661259
DarkChem	[M-H]-	167.156	31661259
DeepCCS	[M+H]+	168.62	30932474
DeepCCS	[M-H]-	166.262	30932474
DeepCCS	[M-2H]-	199.148	30932474
DeepCCS	[M+Na]+	174.714	30932474
AllCCS	[M+H]+	162.2	32859911
AllCCS	[M+H-H2O]+	158.3	32859911
AllCCS	[M+NH4]+	165.9	32859911
AllCCS	[M+Na]+	166.9	32859911
AllCCS	[M-H]-	165.4	32859911
AllCCS	[M+Na-2H]-	164.8	32859911
AllCCS	[M+HCOO]-	164.2	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.	7.84 minutes	32390414
Predicted by Siyang on May 30, 2022	14.1528 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.1 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1965.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	403.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	189.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	209.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	288.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	592.3 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	529.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	111.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1241.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	515.2 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	1285.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	405.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	423.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	374.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	319.3 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	16.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Vignafuran	COC1=CC2=C(C=C(O2)C2=C(OC)C=C(O)C=C2)C=C1	3919.0	Standard polar	33892256
Vignafuran	COC1=CC2=C(C=C(O2)C2=C(OC)C=C(O)C=C2)C=C1	2439.5	Standard non polar	33892256
Vignafuran	COC1=CC2=C(C=C(O2)C2=C(OC)C=C(O)C=C2)C=C1	2632.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Vignafuran,1TMS,isomer #1	COC1=CC=C2C=C(C3=CC=C(O[Si](C)(C)C)C=C3OC)OC2=C1	2648.1	Semi standard non polar	33892256
Vignafuran,1TBDMS,isomer #1	COC1=CC=C2C=C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3OC)OC2=C1	2889.4	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 - Vignafuran GC-MS (Non-derivatized) - 70eV, Positive	splash10-05du-0290000000-678fa416099de46093ce	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vignafuran GC-MS (1 TMS) - 70eV, Positive	splash10-00b9-4389000000-5d90f43e105e7f56d417	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vignafuran 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 - Vignafuran 10V, Positive-QTOF	splash10-00di-0090000000-71534b7080646d7d8e9d	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vignafuran 20V, Positive-QTOF	splash10-00di-0090000000-8185285362e1affaba28	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vignafuran 40V, Positive-QTOF	splash10-07ko-2390000000-980b6e9eeee3c2e9215a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vignafuran 10V, Negative-QTOF	splash10-014i-0090000000-1acc694e6728a2a1b386	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vignafuran 20V, Negative-QTOF	splash10-014i-0090000000-8ade677fac31f22d914b	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vignafuran 40V, Negative-QTOF	splash10-014r-3970000000-735d4798d1e49e43da9e	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vignafuran 10V, Positive-QTOF	splash10-00di-0090000000-cfedaa36beb953194222	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vignafuran 20V, Positive-QTOF	splash10-00di-0190000000-b164076d107beec6645d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vignafuran 40V, Positive-QTOF	splash10-000i-0960000000-c1f5d997a58e56fc15a5	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vignafuran 10V, Negative-QTOF	splash10-014i-0090000000-6871b36f9793cdefd019	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vignafuran 20V, Negative-QTOF	splash10-014i-0090000000-fba2c953c1b5684b0df0	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vignafuran 40V, Negative-QTOF	splash10-00fs-1890000000-181613c5abe83e7a6228	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

441958

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1839391

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 Vignafuran (HMDB0033940)

MOL for HMDB0033940 (Vignafuran)

3D MOL for HMDB0033940 (Vignafuran)

3D SDF for HMDB0033940 (Vignafuran)

3D-SDF for HMDB0033940 (Vignafuran)

PDB for HMDB0033940 (Vignafuran)

3D PDB for HMDB0033940 (Vignafuran)

SMILES for HMDB0033940 (Vignafuran)

INCHI for HMDB0033940 (Vignafuran)

Structure for HMDB0033940 (Vignafuran)

3D Structure for HMDB0033940 (Vignafuran)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra