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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:44:41 UTC

Update Date

2022-03-07 02:53:04 UTC

HMDB ID

HMDB0031657

Secondary Accession Numbers

HMDB31657

Metabolite Identification

Common Name

Ferreirin

Description

Ferreirin belongs to the class of organic compounds known as 4'-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C4' atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one. Thus, ferreirin is considered to be a flavonoid. Ferreirin exists in all living organisms, ranging from bacteria to humans. Ferreirin has been detected, but not quantified in, pigeon peas (Cajanus cajan) and pulses. This could make ferreirin a potential biomarker for the consumption of these foods. Ferreirin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on Ferreirin.

Structure

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

HMDB0031657
     RDKit          3D
Ferreirin
 36 38  0  0  0  0  0  0  0  0999 V2000
    6.1903   -0.6141   -0.6852 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3696   -0.0797    0.3209 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9881    0.1256    0.2475 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2728   -0.1675   -0.8955 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8928    0.0483   -0.9048 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1859    0.5384    0.1545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2193    0.6221    0.3130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9456    1.7947   -0.3875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1685    1.9081    0.4212 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9882    0.7503    0.2900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3446    0.8122    0.5149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1216   -0.3144    0.3727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4916   -0.2370    0.6213 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5590   -1.5350   -0.0035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2075   -1.6125   -0.2315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6410   -2.8446   -0.6198 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3915   -0.4767   -0.0855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9612   -0.5353   -0.3213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4844   -1.4666   -0.9832 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9512    0.8275    1.3101 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3090    1.3309    2.4620 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3149    0.6269    1.3510 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8366   -0.3919   -1.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2420   -0.3414   -0.6498 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1167   -1.7537   -0.5138 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8190   -0.5504   -1.7282 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4097   -0.2164   -1.8073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5397    0.6454    1.3590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1780    1.5250   -1.4229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3800    2.7121   -0.3139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7306    1.7877    0.8087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9045    0.6549    0.9106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2383   -2.3600   -0.0963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1859   -3.6881   -0.7684 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8828    1.6031    3.2447 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8994    0.8721    2.2587 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  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
  6 20  1  0
 20 21  1  0
 20 22  2  0
 22  3  1  0
 18  7  1  0
 17 10  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
 11 31  1  0
 13 32  1  0
 14 33  1  0
 16 34  1  0
 21 35  1  0
 22 36  1  0
M  END


  Mrv0541 05061306032D          

 22 24  0  0  0  0            999 V2000
    7.1447    3.3000    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
    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
    5.7158    2.4750    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
    0.7145    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
    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
    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
    1.4289    3.3000    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
    6.4302    3.7125    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  4  2  0  0  0  0
  8  5  1  0  0  0  0
  9  2  1  0  0  0  0
  9  6  2  0  0  0  0
 10  3  1  0  0  0  0
 11  7  1  0  0  0  0
 11 10  1  0  0  0  0
 12  6  1  0  0  0  0
 12 10  2  0  0  0  0
 13  4  1  0  0  0  0
 14  5  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 12  1  0  0  0  0
 19 13  1  0  0  0  0
 20 16  2  0  0  0  0
 21  1  1  0  0  0  0
 21  9  1  0  0  0  0
 22  7  1  0  0  0  0
 22 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031657

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(O)=C(C=C1)C1COC2=CC(O)=CC(O)=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O6/c1-21-9-2-3-10(12(18)6-9)11-7-22-14-5-8(17)4-13(19)15(14)16(11)20/h2-6,11,17-19H,7H2,1H3

> <INCHI_KEY>
CBEPNYOFLRIAGR-UHFFFAOYSA-N

> <FORMULA>
C16H14O6

> <MOLECULAR_WEIGHT>
302.2788

> <EXACT_MASS>
302.07903818

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
29.44923585878874

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-3-(2-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
2.49

> <JCHEM_LOGP>
2.5699868483333326

> <ALOGPS_LOGS>
-3.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.208084436345667

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.884485665551921

> <JCHEM_PKA_STRONGEST_BASIC>
-3.864899029877656

> <JCHEM_POLAR_SURFACE_AREA>
96.22

> <JCHEM_REFRACTIVITY>
78.1397

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.67e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ferreirin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0031657
     RDKit          3D
Ferreirin
 36 38  0  0  0  0  0  0  0  0999 V2000
    6.1903   -0.6141   -0.6852 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3696   -0.0797    0.3209 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9881    0.1256    0.2475 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2728   -0.1675   -0.8955 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8928    0.0483   -0.9048 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1859    0.5384    0.1545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2193    0.6221    0.3130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9456    1.7947   -0.3875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1685    1.9081    0.4212 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9882    0.7503    0.2900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3446    0.8122    0.5149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1216   -0.3144    0.3727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4916   -0.2370    0.6213 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5590   -1.5350   -0.0035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2075   -1.6125   -0.2315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6410   -2.8446   -0.6198 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3915   -0.4767   -0.0855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9612   -0.5353   -0.3213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4844   -1.4666   -0.9832 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9512    0.8275    1.3101 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3090    1.3309    2.4620 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3149    0.6269    1.3510 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8366   -0.3919   -1.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2420   -0.3414   -0.6498 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1167   -1.7537   -0.5138 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8190   -0.5504   -1.7282 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4097   -0.2164   -1.8073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5397    0.6454    1.3590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1780    1.5250   -1.4229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3800    2.7121   -0.3139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7306    1.7877    0.8087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9045    0.6549    0.9106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2383   -2.3600   -0.0963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1859   -3.6881   -0.7684 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8828    1.6031    3.2447 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8994    0.8721    2.2587 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  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
  6 20  1  0
 20 21  1  0
 20 22  2  0
 22  3  1  0
 18  7  1  0
 17 10  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
 11 31  1  0
 13 32  1  0
 14 33  1  0
 16 34  1  0
 21 35  1  0
 22 36  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      13.337   6.160   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       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.669   4.620   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       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.669   6.160   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       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.667   6.160   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      12.003   6.930   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    9                                                       
CONECT    3    2   10                                                       
CONECT    4    8   13                                                       
CONECT    5    8   14                                                       
CONECT    6    9   12                                                       
CONECT    7   11   22                                                       
CONECT    8    4    5   17                                                  
CONECT    9    2    6   21                                                  
CONECT   10    3   11   12                                                  
CONECT   11    7   10   16                                                  
CONECT   12    6   10   18                                                  
CONECT   13    4   15   19                                                  
CONECT   14    5   15   22                                                  
CONECT   15   13   14   16                                                  
CONECT   16   11   15   20                                                  
CONECT   17    8                                                            
CONECT   18   12                                                            
CONECT   19   13                                                            
CONECT   20   16                                                            
CONECT   21    1    9                                                       
CONECT   22    7   14                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0031657
HETATM    1  C1  UNL     1       6.190  -0.614  -0.685  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.370  -0.080   0.321  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.988   0.126   0.248  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.273  -0.168  -0.896  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.893   0.048  -0.905  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.186   0.538   0.154  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.219   0.622   0.313  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.946   1.795  -0.388  1.00  0.00           C  
HETATM    9  O2  UNL     1      -2.168   1.908   0.421  1.00  0.00           O  
HETATM   10  C8  UNL     1      -2.988   0.750   0.290  1.00  0.00           C  
HETATM   11  C9  UNL     1      -4.345   0.812   0.515  1.00  0.00           C  
HETATM   12  C10 UNL     1      -5.122  -0.314   0.373  1.00  0.00           C  
HETATM   13  O3  UNL     1      -6.492  -0.237   0.621  1.00  0.00           O  
HETATM   14  C11 UNL     1      -4.559  -1.535  -0.004  1.00  0.00           C  
HETATM   15  C12 UNL     1      -3.208  -1.613  -0.232  1.00  0.00           C  
HETATM   16  O4  UNL     1      -2.641  -2.845  -0.620  1.00  0.00           O  
HETATM   17  C13 UNL     1      -2.392  -0.477  -0.085  1.00  0.00           C  
HETATM   18  C14 UNL     1      -0.961  -0.535  -0.321  1.00  0.00           C  
HETATM   19  O5  UNL     1      -0.484  -1.467  -0.983  1.00  0.00           O  
HETATM   20  C15 UNL     1       1.951   0.827   1.310  1.00  0.00           C  
HETATM   21  O6  UNL     1       1.309   1.331   2.462  1.00  0.00           O  
HETATM   22  C16 UNL     1       3.315   0.627   1.351  1.00  0.00           C  
HETATM   23  H1  UNL     1       5.837  -0.392  -1.729  1.00  0.00           H  
HETATM   24  H2  UNL     1       7.242  -0.341  -0.650  1.00  0.00           H  
HETATM   25  H3  UNL     1       6.117  -1.754  -0.514  1.00  0.00           H  
HETATM   26  H4  UNL     1       3.819  -0.550  -1.728  1.00  0.00           H  
HETATM   27  H5  UNL     1       1.410  -0.216  -1.807  1.00  0.00           H  
HETATM   28  H6  UNL     1      -0.540   0.645   1.359  1.00  0.00           H  
HETATM   29  H7  UNL     1      -1.178   1.525  -1.423  1.00  0.00           H  
HETATM   30  H8  UNL     1      -0.380   2.712  -0.314  1.00  0.00           H  
HETATM   31  H9  UNL     1      -4.731   1.788   0.809  1.00  0.00           H  
HETATM   32  H10 UNL     1      -6.905   0.655   0.911  1.00  0.00           H  
HETATM   33  H11 UNL     1      -5.238  -2.360  -0.096  1.00  0.00           H  
HETATM   34  H12 UNL     1      -3.186  -3.688  -0.768  1.00  0.00           H  
HETATM   35  H13 UNL     1       1.883   1.603   3.245  1.00  0.00           H  
HETATM   36  H14 UNL     1       3.899   0.872   2.259  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    6   27
CONECT    6    7   20
CONECT    7    8   18   28
CONECT    8    9   29   30
CONECT    9   10
CONECT   10   11   11   17
CONECT   11   12   31
CONECT   12   13   14   14
CONECT   13   32
CONECT   14   15   33
CONECT   15   16   17   17
CONECT   16   34
CONECT   17   18
CONECT   18   19   19
CONECT   20   21   22   22
CONECT   21   35
CONECT   22   36
END

HMDB0031657
     RDKit          3D
Ferreirin
 36 38  0  0  0  0  0  0  0  0999 V2000
    6.1903   -0.6141   -0.6852 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3696   -0.0797    0.3209 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9881    0.1256    0.2475 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2728   -0.1675   -0.8955 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8928    0.0483   -0.9048 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1859    0.5384    0.1545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2193    0.6221    0.3130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9456    1.7947   -0.3875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1685    1.9081    0.4212 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9882    0.7503    0.2900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3446    0.8122    0.5149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1216   -0.3144    0.3727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4916   -0.2370    0.6213 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5590   -1.5350   -0.0035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2075   -1.6125   -0.2315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6410   -2.8446   -0.6198 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3915   -0.4767   -0.0855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9612   -0.5353   -0.3213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4844   -1.4666   -0.9832 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9512    0.8275    1.3101 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3090    1.3309    2.4620 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3149    0.6269    1.3510 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8366   -0.3919   -1.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2420   -0.3414   -0.6498 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1167   -1.7537   -0.5138 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8190   -0.5504   -1.7282 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4097   -0.2164   -1.8073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5397    0.6454    1.3590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1780    1.5250   -1.4229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3800    2.7121   -0.3139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7306    1.7877    0.8087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9045    0.6549    0.9106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2383   -2.3600   -0.0963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1859   -3.6881   -0.7684 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8828    1.6031    3.2447 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8994    0.8721    2.2587 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  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
  6 20  1  0
 20 21  1  0
 20 22  2  0
 22  3  1  0
 18  7  1  0
 17 10  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
 11 31  1  0
 13 32  1  0
 14 33  1  0
 16 34  1  0
 21 35  1  0
 22 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,3-Dihydro-5,7-dihydroxy-3-(2-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one	ChEBI
2',5,7-Trihydroxy-4'-methoxyisoflavanone	HMDB

Chemical Formula

C₁₆H₁₄O₆

Average Molecular Weight

302.2788

Monoisotopic Molecular Weight

302.07903818

IUPAC Name

5,7-dihydroxy-3-(2-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

ferreirin

CAS Registry Number

32898-79-6

SMILES

COC1=CC(O)=C(C=C1)C1COC2=CC(O)=CC(O)=C2C1=O

InChI Identifier

InChI=1S/C16H14O6/c1-21-9-2-3-10(12(18)6-9)11-7-22-14-5-8(17)4-13(19)15(14)16(11)20/h2-6,11,17-19H,7H2,1H3

InChI Key

CBEPNYOFLRIAGR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 4'-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C4' atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

O-methylated isoflavonoids

Direct Parent

4'-O-methylated isoflavonoids

Alternative Parents

Substituents

4p-methoxyisoflavonoid
Isoflavanol
Isoflavanone
Hydroxyisoflavonoid
Isoflavan
Chromone
Methoxyphenol
Benzopyran
1-benzopyran
Chromane
Aryl alkyl ketone
Aryl ketone
Phenol ether
Phenoxy compound
Methoxybenzene
Anisole
1-hydroxy-2-unsubstituted benzenoid
Phenol
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Ketone
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

hydroxyisoflavanone (CHEBI:5018 )
methoxyisoflavanone (CHEBI:5018 )
isoflavanones (C10419 )
Isoflavonoids (C10419 )
Isoflavonoids (LMPK12050501 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0031657)
Cytoplasm (HMDB: HMDB0031657)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031657)

Source

Endogenous

Endogenous (HMDB: HMDB0031657)

Plant

Plant (HMDB: HMDB0031657)
Fabaceae (HMDB: HMDB0031657)

Exogenous

Food

Food (HMDB: HMDB0031657)

Pulse

Pea

Pigeon pea (FooDB: FOOD00037)

Pulses (FooDB: FOOD00867)

Exogenous (HMDB: HMDB0031657)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	210 - 212 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	226.7 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	0.17 g/L	ALOGPS
logP	2.49	ALOGPS
logP	2.57	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	7.88	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	78.14 m³·mol⁻¹	ChemAxon
Polarizability	29.45 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]+	168.846	31661259
DarkChem	[M-H]-	171.767	31661259
DeepCCS	[M+H]+	169.903	30932474
DeepCCS	[M-H]-	167.545	30932474
DeepCCS	[M-2H]-	200.431	30932474
DeepCCS	[M+Na]+	175.996	30932474
AllCCS	[M+H]+	169.9	32859911
AllCCS	[M+H-H2O]+	166.3	32859911
AllCCS	[M+NH4]+	173.3	32859911
AllCCS	[M+Na]+	174.2	32859911
AllCCS	[M-H]-	171.4	32859911
AllCCS	[M+Na-2H]-	170.9	32859911
AllCCS	[M+HCOO]-	170.6	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.	6.92 minutes	32390414
Predicted by Siyang on May 30, 2022	12.7091 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.31 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2227.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	282.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	136.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	167.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	219.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	646.4 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	637.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	85.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1046.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	448.4 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	1459.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	385.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	398.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	448.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	155.7 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	158.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ferreirin	COC1=CC(O)=C(C=C1)C1COC2=CC(O)=CC(O)=C2C1=O	4136.9	Standard polar	33892256
Ferreirin	COC1=CC(O)=C(C=C1)C1COC2=CC(O)=CC(O)=C2C1=O	2973.2	Standard non polar	33892256
Ferreirin	COC1=CC(O)=C(C=C1)C1COC2=CC(O)=CC(O)=C2C1=O	3047.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ferreirin,1TMS,isomer #1	COC1=CC=C(C2COC3=CC(O)=CC(O)=C3C2=O)C(O[Si](C)(C)C)=C1	2901.8	Semi standard non polar	33892256
Ferreirin,1TMS,isomer #2	COC1=CC=C(C2COC3=CC(O[Si](C)(C)C)=CC(O)=C3C2=O)C(O)=C1	2912.5	Semi standard non polar	33892256
Ferreirin,1TMS,isomer #3	COC1=CC=C(C2COC3=CC(O)=CC(O[Si](C)(C)C)=C3C2=O)C(O)=C1	2952.6	Semi standard non polar	33892256
Ferreirin,2TMS,isomer #1	COC1=CC=C(C2COC3=CC(O[Si](C)(C)C)=CC(O)=C3C2=O)C(O[Si](C)(C)C)=C1	2794.1	Semi standard non polar	33892256
Ferreirin,2TMS,isomer #2	COC1=CC=C(C2COC3=CC(O)=CC(O[Si](C)(C)C)=C3C2=O)C(O[Si](C)(C)C)=C1	2880.3	Semi standard non polar	33892256
Ferreirin,2TMS,isomer #3	COC1=CC=C(C2COC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C2=O)C(O)=C1	2869.3	Semi standard non polar	33892256
Ferreirin,3TMS,isomer #1	COC1=CC=C(C2COC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C2=O)C(O[Si](C)(C)C)=C1	2765.4	Semi standard non polar	33892256
Ferreirin,1TBDMS,isomer #1	COC1=CC=C(C2COC3=CC(O)=CC(O)=C3C2=O)C(O[Si](C)(C)C(C)(C)C)=C1	3168.5	Semi standard non polar	33892256
Ferreirin,1TBDMS,isomer #2	COC1=CC=C(C2COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C2=O)C(O)=C1	3169.6	Semi standard non polar	33892256
Ferreirin,1TBDMS,isomer #3	COC1=CC=C(C2COC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C(O)=C1	3211.9	Semi standard non polar	33892256
Ferreirin,2TBDMS,isomer #1	COC1=CC=C(C2COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C2=O)C(O[Si](C)(C)C(C)(C)C)=C1	3299.7	Semi standard non polar	33892256
Ferreirin,2TBDMS,isomer #2	COC1=CC=C(C2COC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C(O[Si](C)(C)C(C)(C)C)=C1	3355.4	Semi standard non polar	33892256
Ferreirin,2TBDMS,isomer #3	COC1=CC=C(C2COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C(O)=C1	3361.5	Semi standard non polar	33892256
Ferreirin,3TBDMS,isomer #1	COC1=CC=C(C2COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C(O[Si](C)(C)C(C)(C)C)=C1	3466.9	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 - Ferreirin GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dr-0971000000-e1a752f1fe5e5bef99b1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ferreirin GC-MS (3 TMS) - 70eV, Positive	splash10-0w91-2790650000-726641b201ef5d1f317f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ferreirin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ferreirin 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 - Ferreirin 10V, Positive-QTOF	splash10-0udi-0439000000-c432e250004639a5b97a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ferreirin 20V, Positive-QTOF	splash10-0udr-0933000000-f509a1599d51f22e9c87	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ferreirin 40V, Positive-QTOF	splash10-0f79-2910000000-9f49b49b0b8876d88ff1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ferreirin 10V, Negative-QTOF	splash10-0udi-0019000000-984f80d99703c2cf5dd9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ferreirin 20V, Negative-QTOF	splash10-0udi-1879000000-cd7addbf04b682ec9998	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ferreirin 40V, Negative-QTOF	splash10-006x-9620000000-f191e4817cbcda7e0cf8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ferreirin 10V, Negative-QTOF	splash10-0udi-0109000000-ca8f0442f17fc86c01ad	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ferreirin 20V, Negative-QTOF	splash10-0udi-0598000000-852bb2bbf10d2bceeb65	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ferreirin 40V, Negative-QTOF	splash10-0uxr-1390000000-18a196624ec42760dd4a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ferreirin 10V, Positive-QTOF	splash10-0ufr-0907000000-a782d3f05e3c9b06fc83	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ferreirin 20V, Positive-QTOF	splash10-0udj-0901000000-15d93d0c4825184dd82e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ferreirin 40V, Positive-QTOF	splash10-1009-3920000000-30644f950f2320dc8b6b	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

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

442771

PDB ID

Not Available

ChEBI ID

5018

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1827331

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

Ferreirin → 3,4,5-trihydroxy-6-{[7-hydroxy-3-(2-hydroxy-4-methoxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-5-yl]oxy}oxane-2-carboxylic acid	details
Ferreirin → 3,4,5-trihydroxy-6-{[5-hydroxy-3-(2-hydroxy-4-methoxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}oxane-2-carboxylic acid	details
Ferreirin → 6-[2-(5,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-3-yl)-5-methoxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid	details

Showing metabocard for Ferreirin (HMDB0031657)

MOL for HMDB0031657 (Ferreirin)

3D MOL for HMDB0031657 (Ferreirin)

3D SDF for HMDB0031657 (Ferreirin)

3D-SDF for HMDB0031657 (Ferreirin)

PDB for HMDB0031657 (Ferreirin)

3D PDB for HMDB0031657 (Ferreirin)

SMILES for HMDB0031657 (Ferreirin)

INCHI for HMDB0031657 (Ferreirin)

Structure for HMDB0031657 (Ferreirin)

3D Structure for HMDB0031657 (Ferreirin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions