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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:30:43 UTC

Update Date

2022-03-07 02:52:11 UTC

HMDB ID

HMDB0029491

Secondary Accession Numbers

HMDB29491

Metabolite Identification

Common Name

Isoferreirin

Description

Isoferreirin belongs to the class of organic compounds known as 2'-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C2' atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one. Thus, isoferreirin is considered to be a flavonoid. Isoferreirin has been detected, but not quantified in, a few different foods, such as fruits, lima beans (Phaseolus lunatus), and scarlet beans (Phaseolus coccineus). This could make isoferreirin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Isoferreirin.

Structure

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

HMDB0029491
     RDKit          3D
Isoferreirin
 36 38  0  0  0  0  0  0  0  0999 V2000
    3.0210    1.4898    2.4731 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1341    1.1916    1.4334 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4186    0.3845    0.3451 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6724   -0.1802    0.2746 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0247   -1.0053   -0.8014 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2799   -1.5786   -0.8857 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1113   -1.2516   -1.7921 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8620   -0.6712   -1.6923 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4723    0.1475   -0.6520 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1589    0.7711   -0.4956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6426    0.8328   -1.7819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8965    1.4415   -1.4420 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7386    0.7367   -0.5950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1205    0.8202   -0.7331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8690    0.0802    0.1558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2565    0.1785    0.0009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3147   -0.6957    1.1220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9096   -0.7754    1.2572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3895   -1.5638    2.2379 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1216   -0.0480    0.3864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6509   -0.0698    0.4541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0931   -0.7823    1.2945 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6675    2.3606    3.0678 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0057    1.7200    1.9757 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1008    0.6349    3.1651 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4427   -0.0248    1.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5238   -2.4627   -0.5062 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3658   -1.9023   -2.6471 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1478   -0.8692   -2.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2841    1.8015   -0.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8562   -0.1468   -2.2161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1685    1.5358   -2.5211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5616    1.4358   -1.4992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6768   -0.5010   -0.6365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9286   -1.2626    1.8003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4982   -1.7715    2.5097 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  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
  9  3  1  0
 21 10  1  0
 20 13  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
  8 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  0
 19 36  1  0
M  END


  Mrv0541 05061304472D          

 22 24  0  0  0  0            999 V2000
    4.2868    0.8250    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
    5.7158    2.4750    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
    1.4289    2.4750    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
    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
    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
    5.0013    1.2375    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  5  2  0  0  0  0
  9  4  2  0  0  0  0
  9  6  1  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  4  1  0  0  0  0
 13  5  1  0  0  0  0
 13 10  2  0  0  0  0
 14  6  2  0  0  0  0
 15 12  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>
HMDB0029491

> <DATABASE_NAME>
hmdb

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

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

> <INCHI_KEY>
VODZWHSRITUHNI-UHFFFAOYSA-N

> <FORMULA>
C16H14O6

> <MOLECULAR_WEIGHT>
302.2788

> <EXACT_MASS>
302.07903818

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
29.630596849961336

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.48

> <JCHEM_LOGP>
2.5699868483333326

> <ALOGPS_LOGS>
-3.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.432385299310093

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.893577284696494

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8648991031021565

> <JCHEM_POLAR_SURFACE_AREA>
96.22

> <JCHEM_REFRACTIVITY>
78.1397

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.48e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isoferreirin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029491
     RDKit          3D
Isoferreirin
 36 38  0  0  0  0  0  0  0  0999 V2000
    3.0210    1.4898    2.4731 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1341    1.1916    1.4334 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4186    0.3845    0.3451 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6724   -0.1802    0.2746 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0247   -1.0053   -0.8014 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2799   -1.5786   -0.8857 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1113   -1.2516   -1.7921 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8620   -0.6712   -1.6923 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4723    0.1475   -0.6520 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1589    0.7711   -0.4956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6426    0.8328   -1.7819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8965    1.4415   -1.4420 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7386    0.7367   -0.5950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1205    0.8202   -0.7331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8690    0.0802    0.1558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2565    0.1785    0.0009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3147   -0.6957    1.1220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9096   -0.7754    1.2572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3895   -1.5638    2.2379 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1216   -0.0480    0.3864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6509   -0.0698    0.4541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0931   -0.7823    1.2945 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6675    2.3606    3.0678 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0057    1.7200    1.9757 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1008    0.6349    3.1651 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4427   -0.0248    1.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5238   -2.4627   -0.5062 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3658   -1.9023   -2.6471 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1478   -0.8692   -2.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2841    1.8015   -0.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8562   -0.1468   -2.2161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1685    1.5358   -2.5211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5616    1.4358   -1.4992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6768   -0.5010   -0.6365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9286   -1.2626    1.8003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4982   -1.7715    2.5097 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  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
  9  3  1  0
 21 10  1  0
 20 13  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
  8 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  0
 19 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       8.002   1.540   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      10.669   4.620   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       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336   3.850   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       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       9.336   2.310   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    9   12                                                       
CONECT    5    8   13                                                       
CONECT    6    9   14                                                       
CONECT    7   11   22                                                       
CONECT    8    2    5   17                                                  
CONECT    9    4    6   18                                                  
CONECT   10    3   11   13                                                  
CONECT   11    7   10   16                                                  
CONECT   12    4   15   19                                                  
CONECT   13    5   10   21                                                  
CONECT   14    6   15   22                                                  
CONECT   15   12   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    HMDB0029491
HETATM    1  C1  UNL     1       3.021   1.490   2.473  1.00  0.00           C  
HETATM    2  O1  UNL     1       2.134   1.192   1.433  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.419   0.384   0.345  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.672  -0.180   0.275  1.00  0.00           C  
HETATM    5  C4  UNL     1       4.025  -1.005  -0.801  1.00  0.00           C  
HETATM    6  O2  UNL     1       5.280  -1.579  -0.886  1.00  0.00           O  
HETATM    7  C5  UNL     1       3.111  -1.252  -1.792  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.862  -0.671  -1.692  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.472   0.148  -0.652  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.159   0.771  -0.496  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.643   0.833  -1.782  1.00  0.00           C  
HETATM   12  O3  UNL     1      -1.897   1.442  -1.442  1.00  0.00           O  
HETATM   13  C10 UNL     1      -2.739   0.737  -0.595  1.00  0.00           C  
HETATM   14  C11 UNL     1      -4.121   0.820  -0.733  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.869   0.080   0.156  1.00  0.00           C  
HETATM   16  O4  UNL     1      -6.257   0.179   0.001  1.00  0.00           O  
HETATM   17  C13 UNL     1      -4.315  -0.696   1.122  1.00  0.00           C  
HETATM   18  C14 UNL     1      -2.910  -0.775   1.257  1.00  0.00           C  
HETATM   19  O5  UNL     1      -2.390  -1.564   2.238  1.00  0.00           O  
HETATM   20  C15 UNL     1      -2.122  -0.048   0.386  1.00  0.00           C  
HETATM   21  C16 UNL     1      -0.651  -0.070   0.454  1.00  0.00           C  
HETATM   22  O6  UNL     1      -0.093  -0.782   1.295  1.00  0.00           O  
HETATM   23  H1  UNL     1       2.667   2.361   3.068  1.00  0.00           H  
HETATM   24  H2  UNL     1       4.006   1.720   1.976  1.00  0.00           H  
HETATM   25  H3  UNL     1       3.101   0.635   3.165  1.00  0.00           H  
HETATM   26  H4  UNL     1       4.443  -0.025   1.025  1.00  0.00           H  
HETATM   27  H5  UNL     1       5.524  -2.463  -0.506  1.00  0.00           H  
HETATM   28  H6  UNL     1       3.366  -1.902  -2.647  1.00  0.00           H  
HETATM   29  H7  UNL     1       1.148  -0.869  -2.463  1.00  0.00           H  
HETATM   30  H8  UNL     1       0.284   1.801  -0.125  1.00  0.00           H  
HETATM   31  H9  UNL     1      -0.856  -0.147  -2.216  1.00  0.00           H  
HETATM   32  H10 UNL     1      -0.168   1.536  -2.521  1.00  0.00           H  
HETATM   33  H11 UNL     1      -4.562   1.436  -1.499  1.00  0.00           H  
HETATM   34  H12 UNL     1      -6.677  -0.501  -0.636  1.00  0.00           H  
HETATM   35  H13 UNL     1      -4.929  -1.263   1.800  1.00  0.00           H  
HETATM   36  H14 UNL     1      -1.498  -1.772   2.510  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4    9
CONECT    4    5   26
CONECT    5    6    7    7
CONECT    6   27
CONECT    7    8   28
CONECT    8    9    9   29
CONECT    9   10
CONECT   10   11   21   30
CONECT   11   12   31   32
CONECT   12   13
CONECT   13   14   14   20
CONECT   14   15   33
CONECT   15   16   17   17
CONECT   16   34
CONECT   17   18   35
CONECT   18   19   20   20
CONECT   19   36
CONECT   20   21
CONECT   21   22   22
END

HMDB0029491
     RDKit          3D
Isoferreirin
 36 38  0  0  0  0  0  0  0  0999 V2000
    3.0210    1.4898    2.4731 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1341    1.1916    1.4334 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4186    0.3845    0.3451 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6724   -0.1802    0.2746 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0247   -1.0053   -0.8014 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2799   -1.5786   -0.8857 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1113   -1.2516   -1.7921 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8620   -0.6712   -1.6923 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4723    0.1475   -0.6520 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1589    0.7711   -0.4956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6426    0.8328   -1.7819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8965    1.4415   -1.4420 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7386    0.7367   -0.5950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1205    0.8202   -0.7331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8690    0.0802    0.1558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2565    0.1785    0.0009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3147   -0.6957    1.1220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9096   -0.7754    1.2572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3895   -1.5638    2.2379 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1216   -0.0480    0.3864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6509   -0.0698    0.4541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0931   -0.7823    1.2945 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6675    2.3606    3.0678 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0057    1.7200    1.9757 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1008    0.6349    3.1651 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4427   -0.0248    1.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5238   -2.4627   -0.5062 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3658   -1.9023   -2.6471 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1478   -0.8692   -2.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2841    1.8015   -0.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8562   -0.1468   -2.2161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1685    1.5358   -2.5211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5616    1.4358   -1.4992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6768   -0.5010   -0.6365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9286   -1.2626    1.8003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4982   -1.7715    2.5097 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  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
  9  3  1  0
 21 10  1  0
 20 13  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
  8 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  0
 19 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4',5,7-Trihydroxy-2'-methoxyisoflavanone	HMDB

Chemical Formula

C₁₆H₁₄O₆

Average Molecular Weight

302.2788

Monoisotopic Molecular Weight

302.07903818

IUPAC Name

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

Traditional Name

isoferreirin

CAS Registry Number

76656-75-2

SMILES

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

InChI Identifier

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

InChI Key

VODZWHSRITUHNI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2'-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C2' 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

2'-O-methylated isoflavonoids

Alternative Parents

Substituents

2p-methoxyisoflavonoid-skeleton
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

Isoflavonoids (LMPK12050503 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0029491)
Cytoplasm (HMDB: HMDB0029491)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029491)

Source

Endogenous

Endogenous (HMDB: HMDB0029491)

Plant

Plant (HMDB: HMDB0029491)
Fabaceae (HMDB: HMDB0029491)

Exogenous

Food

Food (HMDB: HMDB0029491)

Pulse

Bean

Lima bean (FooDB: FOOD00133)
Scarlet bean (FooDB: FOOD00132)

Fruit

Fruits (FooDB: FOOD00871)

Process

Not Available

Role

Not Available

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	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	0.15 g/L	ALOGPS
logP	2.48	ALOGPS
logP	2.57	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	7.89	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	29.63 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]+	170.543	31661259
DarkChem	[M-H]-	169.582	31661259
DeepCCS	[M+H]+	169.612	30932474
DeepCCS	[M-H]-	167.254	30932474
DeepCCS	[M-2H]-	200.14	30932474
DeepCCS	[M+Na]+	175.705	30932474
AllCCS	[M+H]+	169.5	32859911
AllCCS	[M+H-H2O]+	165.8	32859911
AllCCS	[M+NH4]+	172.8	32859911
AllCCS	[M+Na]+	173.8	32859911
AllCCS	[M-H]-	170.9	32859911
AllCCS	[M+Na-2H]-	170.3	32859911
AllCCS	[M+HCOO]-	169.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isoferreirin	COC1=C(C=CC(O)=C1)C1COC2=CC(O)=CC(O)=C2C1=O	4121.7	Standard polar	33892256
Isoferreirin	COC1=C(C=CC(O)=C1)C1COC2=CC(O)=CC(O)=C2C1=O	2940.1	Standard non polar	33892256
Isoferreirin	COC1=C(C=CC(O)=C1)C1COC2=CC(O)=CC(O)=C2C1=O	3100.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Isoferreirin,1TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=CC=C1C1COC2=CC(O)=CC(O)=C2C1=O	2919.3	Semi standard non polar	33892256
Isoferreirin,1TMS,isomer #2	COC1=CC(O)=CC=C1C1COC2=CC(O[Si](C)(C)C)=CC(O)=C2C1=O	2906.5	Semi standard non polar	33892256
Isoferreirin,1TMS,isomer #3	COC1=CC(O)=CC=C1C1COC2=CC(O)=CC(O[Si](C)(C)C)=C2C1=O	2940.5	Semi standard non polar	33892256
Isoferreirin,2TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=CC=C1C1COC2=CC(O[Si](C)(C)C)=CC(O)=C2C1=O	2827.9	Semi standard non polar	33892256
Isoferreirin,2TMS,isomer #2	COC1=CC(O[Si](C)(C)C)=CC=C1C1COC2=CC(O)=CC(O[Si](C)(C)C)=C2C1=O	2894.5	Semi standard non polar	33892256
Isoferreirin,2TMS,isomer #3	COC1=CC(O)=CC=C1C1COC2=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C2C1=O	2889.5	Semi standard non polar	33892256
Isoferreirin,3TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=CC=C1C1COC2=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C2C1=O	2775.6	Semi standard non polar	33892256
Isoferreirin,1TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1C1COC2=CC(O)=CC(O)=C2C1=O	3192.2	Semi standard non polar	33892256
Isoferreirin,1TBDMS,isomer #2	COC1=CC(O)=CC=C1C1COC2=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C2C1=O	3177.4	Semi standard non polar	33892256
Isoferreirin,1TBDMS,isomer #3	COC1=CC(O)=CC=C1C1COC2=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C2C1=O	3214.1	Semi standard non polar	33892256
Isoferreirin,2TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1C1COC2=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C2C1=O	3334.9	Semi standard non polar	33892256
Isoferreirin,2TBDMS,isomer #2	COC1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1C1COC2=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C2C1=O	3380.1	Semi standard non polar	33892256
Isoferreirin,2TBDMS,isomer #3	COC1=CC(O)=CC=C1C1COC2=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C2C1=O	3374.3	Semi standard non polar	33892256
Isoferreirin,3TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1C1COC2=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C2C1=O	3497.0	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 - Isoferreirin GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dr-0971000000-ee5cfcd61d28041e466d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoferreirin GC-MS (3 TMS) - 70eV, Positive	splash10-0w91-2690650000-8eb3972531ebbafa81ac	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoferreirin 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 - Isoferreirin 10V, Positive-QTOF	splash10-0udi-0439000000-f935d68f92181bd84126	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoferreirin 20V, Positive-QTOF	splash10-0udr-0933000000-938eb046c9246d8aa0c1	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoferreirin 40V, Positive-QTOF	splash10-0f79-3900000000-ee2398fb409ee73b3722	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoferreirin 10V, Negative-QTOF	splash10-0udi-0019000000-0af4c2ca8b44a15cefc2	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoferreirin 20V, Negative-QTOF	splash10-0udi-1869000000-40a81608780e20d6184a	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoferreirin 40V, Negative-QTOF	splash10-006x-9620000000-043ccee68ed8858c4c71	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoferreirin 10V, Positive-QTOF	splash10-0udi-0009000000-d1450f45777bb06cb577	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoferreirin 20V, Positive-QTOF	splash10-0udi-0913000000-1f7abd1a9624c3d18ceb	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoferreirin 40V, Positive-QTOF	splash10-0fvr-1910000000-c1cecbeac21c534c018a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoferreirin 10V, Negative-QTOF	splash10-0udi-0309000000-dcc4dcfe1b2a36efa446	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoferreirin 20V, Negative-QTOF	splash10-0fba-0792000000-db2f5160872db93bc93a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoferreirin 40V, Negative-QTOF	splash10-0f6t-1590000000-81c11f258adfbbf0cb3f	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

FDB000623

KNApSAcK ID

C00009554

Chemspider ID

137998

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

156743

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1809911

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 Isoferreirin (HMDB0029491)

MOL for HMDB0029491 (Isoferreirin)

3D MOL for HMDB0029491 (Isoferreirin)

3D SDF for HMDB0029491 (Isoferreirin)

3D-SDF for HMDB0029491 (Isoferreirin)

PDB for HMDB0029491 (Isoferreirin)

3D PDB for HMDB0029491 (Isoferreirin)

SMILES for HMDB0029491 (Isoferreirin)

INCHI for HMDB0029491 (Isoferreirin)

Structure for HMDB0029491 (Isoferreirin)

3D Structure for HMDB0029491 (Isoferreirin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra