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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:34:50 UTC

Update Date

2022-03-07 02:52:26 UTC

HMDB ID

HMDB0030111

Secondary Accession Numbers

HMDB30111

Metabolite Identification

Common Name

Homoferreirin

Description

Homoferreirin 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, homoferreirin is considered to be a flavonoid. Homoferreirin has been detected, but not quantified in, chickpeas (Cicer arietinum) and pulses. This could make homoferreirin a potential biomarker for the consumption of these foods. Homoferreirin 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 very few articles have been published on Homoferreirin.

Structure

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

HMDB0030111
     RDKit          3D
Homoferreirin
 39 41  0  0  0  0  0  0  0  0999 V2000
    5.9325   -1.4956   -0.6349 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2033   -0.3094   -0.7274 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8300   -0.2399   -0.4209 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1833   -1.3802   -0.0304 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8450   -1.3010    0.2681 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1128   -0.1275    0.1928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3101   -0.1475    0.4092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6908   -0.1179    1.8900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0341   -0.4646    2.0332 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9911   -0.4057    1.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2897   -0.8557    1.2943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2644   -0.8198    0.3200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5568   -1.2866    0.6366 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9568   -0.3330   -0.9225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6588    0.1189   -1.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2793    0.6239   -2.4105 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6916    0.0798   -0.2120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2818    0.5373   -0.4145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1146    1.4365   -1.2640 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7969    1.0152   -0.2036 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0933    2.2036   -0.2718 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6343    3.4259   -0.6252 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1363    0.9373   -0.5032 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8573   -2.1608   -1.4956 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9893   -1.2470   -0.3413 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5333   -2.0388    0.2663 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6405   -2.3646    0.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3414   -2.2280    0.5733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5971   -1.3239    0.2099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5572    0.9672    2.2109 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0210   -0.7561    2.4225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5501   -1.2367    2.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6986   -2.2888    0.4722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7046   -0.3001   -1.6832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8878    0.6859   -3.1960 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8365    4.1182   -1.0137 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4095    3.3633   -1.4018 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0452    3.8738    0.3332 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6734    1.8425   -0.8203 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
 21 22  1  0
 20 23  2  0
 23  3  1  0
 18  7  1  0
 17 10  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  5 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
 11 32  1  0
 13 33  1  0
 14 34  1  0
 16 35  1  0
 22 36  1  0
 22 37  1  0
 22 38  1  0
 23 39  1  0
M  END


  Mrv0541 05061305002D          

 23 25  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
    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
    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
    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
    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
    6.4302    3.7125    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
  4  3  2  0  0  0  0
  9  5  2  0  0  0  0
  9  6  1  0  0  0  0
 10  3  1  0  0  0  0
 10  7  2  0  0  0  0
 11  4  1  0  0  0  0
 12  8  1  0  0  0  0
 12 11  1  0  0  0  0
 13  5  1  0  0  0  0
 14  7  1  0  0  0  0
 14 11  2  0  0  0  0
 15  6  2  0  0  0  0
 16 13  2  0  0  0  0
 16 15  1  0  0  0  0
 17 12  1  0  0  0  0
 17 16  1  0  0  0  0
 18  9  1  0  0  0  0
 19 13  1  0  0  0  0
 20 17  2  0  0  0  0
 21  1  1  0  0  0  0
 21 10  1  0  0  0  0
 22  2  1  0  0  0  0
 22 14  1  0  0  0  0
 23  8  1  0  0  0  0
 23 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030111

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H16O6/c1-21-10-3-4-11(14(7-10)22-2)12-8-23-15-6-9(18)5-13(19)16(15)17(12)20/h3-7,12,18-19H,8H2,1-2H3

> <INCHI_KEY>
LMLDNMHDNFCNCW-UHFFFAOYSA-N

> <FORMULA>
C17H16O6

> <MOLECULAR_WEIGHT>
316.3053

> <EXACT_MASS>
316.094688244

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
31.54850182827974

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.79

> <JCHEM_LOGP>
2.715880904333333

> <ALOGPS_LOGS>
-3.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.629611902196883

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.905964237489206

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8648991031057784

> <JCHEM_POLAR_SURFACE_AREA>
85.22000000000001

> <JCHEM_REFRACTIVITY>
82.622

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.52e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
homoferreirin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030111
     RDKit          3D
Homoferreirin
 39 41  0  0  0  0  0  0  0  0999 V2000
    5.9325   -1.4956   -0.6349 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2033   -0.3094   -0.7274 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8300   -0.2399   -0.4209 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1833   -1.3802   -0.0304 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8450   -1.3010    0.2681 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1128   -0.1275    0.1928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3101   -0.1475    0.4092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6908   -0.1179    1.8900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0341   -0.4646    2.0332 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9911   -0.4057    1.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2897   -0.8557    1.2943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2644   -0.8198    0.3200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5568   -1.2866    0.6366 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9568   -0.3330   -0.9225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6588    0.1189   -1.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2793    0.6239   -2.4105 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6916    0.0798   -0.2120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2818    0.5373   -0.4145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1146    1.4365   -1.2640 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7969    1.0152   -0.2036 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0933    2.2036   -0.2718 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6343    3.4259   -0.6252 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1363    0.9373   -0.5032 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8573   -2.1608   -1.4956 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9893   -1.2470   -0.3413 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5333   -2.0388    0.2663 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6405   -2.3646    0.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3414   -2.2280    0.5733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5971   -1.3239    0.2099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5572    0.9672    2.2109 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0210   -0.7561    2.4225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5501   -1.2367    2.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6986   -2.2888    0.4722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7046   -0.3001   -1.6832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8878    0.6859   -3.1960 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8365    4.1182   -1.0137 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4095    3.3633   -1.4018 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0452    3.8738    0.3332 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6734    1.8425   -0.8203 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
 21 22  1  0
 20 23  2  0
 23  3  1  0
 18  7  1  0
 17 10  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  5 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
 11 32  1  0
 13 33  1  0
 14 34  1  0
 16 35  1  0
 22 36  1  0
 22 37  1  0
 22 38  1  0
 23 39  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       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   2.310   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      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668   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       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+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      12.003   6.930   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2   22                                                            
CONECT    3    4   10                                                       
CONECT    4    3   11                                                       
CONECT    5    9   13                                                       
CONECT    6    9   15                                                       
CONECT    7   10   14                                                       
CONECT    8   12   23                                                       
CONECT    9    5    6   18                                                  
CONECT   10    3    7   21                                                  
CONECT   11    4   12   14                                                  
CONECT   12    8   11   17                                                  
CONECT   13    5   16   19                                                  
CONECT   14    7   11   22                                                  
CONECT   15    6   16   23                                                  
CONECT   16   13   15   17                                                  
CONECT   17   12   16   20                                                  
CONECT   18    9                                                            
CONECT   19   13                                                            
CONECT   20   17                                                            
CONECT   21    1   10                                                       
CONECT   22    2   14                                                       
CONECT   23    8   15                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0030111
HETATM    1  C1  UNL     1       5.933  -1.496  -0.635  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.203  -0.309  -0.727  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.830  -0.240  -0.421  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.183  -1.380  -0.030  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.845  -1.301   0.268  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.113  -0.128   0.193  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.310  -0.147   0.409  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.691  -0.118   1.890  1.00  0.00           C  
HETATM    9  O2  UNL     1      -2.034  -0.465   2.033  1.00  0.00           O  
HETATM   10  C8  UNL     1      -2.991  -0.406   1.031  1.00  0.00           C  
HETATM   11  C9  UNL     1      -4.290  -0.856   1.294  1.00  0.00           C  
HETATM   12  C10 UNL     1      -5.264  -0.820   0.320  1.00  0.00           C  
HETATM   13  O3  UNL     1      -6.557  -1.287   0.637  1.00  0.00           O  
HETATM   14  C11 UNL     1      -4.957  -0.333  -0.922  1.00  0.00           C  
HETATM   15  C12 UNL     1      -3.659   0.119  -1.180  1.00  0.00           C  
HETATM   16  O4  UNL     1      -3.279   0.624  -2.410  1.00  0.00           O  
HETATM   17  C13 UNL     1      -2.692   0.080  -0.212  1.00  0.00           C  
HETATM   18  C14 UNL     1      -1.282   0.537  -0.414  1.00  0.00           C  
HETATM   19  O5  UNL     1      -1.115   1.437  -1.264  1.00  0.00           O  
HETATM   20  C15 UNL     1       1.797   1.015  -0.204  1.00  0.00           C  
HETATM   21  O6  UNL     1       1.093   2.204  -0.272  1.00  0.00           O  
HETATM   22  C16 UNL     1       1.634   3.426  -0.625  1.00  0.00           C  
HETATM   23  C17 UNL     1       3.136   0.937  -0.503  1.00  0.00           C  
HETATM   24  H1  UNL     1       5.857  -2.161  -1.496  1.00  0.00           H  
HETATM   25  H2  UNL     1       6.989  -1.247  -0.341  1.00  0.00           H  
HETATM   26  H3  UNL     1       5.533  -2.039   0.266  1.00  0.00           H  
HETATM   27  H4  UNL     1       3.640  -2.365   0.046  1.00  0.00           H  
HETATM   28  H5  UNL     1       1.341  -2.228   0.573  1.00  0.00           H  
HETATM   29  H6  UNL     1      -0.597  -1.324   0.210  1.00  0.00           H  
HETATM   30  H7  UNL     1      -0.557   0.967   2.211  1.00  0.00           H  
HETATM   31  H8  UNL     1       0.021  -0.756   2.423  1.00  0.00           H  
HETATM   32  H9  UNL     1      -4.550  -1.237   2.283  1.00  0.00           H  
HETATM   33  H10 UNL     1      -6.699  -2.289   0.472  1.00  0.00           H  
HETATM   34  H11 UNL     1      -5.705  -0.300  -1.683  1.00  0.00           H  
HETATM   35  H12 UNL     1      -3.888   0.686  -3.196  1.00  0.00           H  
HETATM   36  H13 UNL     1       0.837   4.118  -1.014  1.00  0.00           H  
HETATM   37  H14 UNL     1       2.409   3.363  -1.402  1.00  0.00           H  
HETATM   38  H15 UNL     1       2.045   3.874   0.333  1.00  0.00           H  
HETATM   39  H16 UNL     1       3.673   1.843  -0.820  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    4   23
CONECT    4    5   27
CONECT    5    6    6   28
CONECT    6    7   20
CONECT    7    8   18   29
CONECT    8    9   30   31
CONECT    9   10
CONECT   10   11   11   17
CONECT   11   12   32
CONECT   12   13   14   14
CONECT   13   33
CONECT   14   15   34
CONECT   15   16   17   17
CONECT   16   35
CONECT   17   18
CONECT   18   19   19
CONECT   20   21   23   23
CONECT   21   22
CONECT   22   36   37   38
CONECT   23   39
END

HMDB0030111
     RDKit          3D
Homoferreirin
 39 41  0  0  0  0  0  0  0  0999 V2000
    5.9325   -1.4956   -0.6349 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2033   -0.3094   -0.7274 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8300   -0.2399   -0.4209 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1833   -1.3802   -0.0304 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8450   -1.3010    0.2681 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1128   -0.1275    0.1928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3101   -0.1475    0.4092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6908   -0.1179    1.8900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0341   -0.4646    2.0332 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9911   -0.4057    1.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2897   -0.8557    1.2943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2644   -0.8198    0.3200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5568   -1.2866    0.6366 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9568   -0.3330   -0.9225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6588    0.1189   -1.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2793    0.6239   -2.4105 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6916    0.0798   -0.2120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2818    0.5373   -0.4145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1146    1.4365   -1.2640 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7969    1.0152   -0.2036 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0933    2.2036   -0.2718 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6343    3.4259   -0.6252 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1363    0.9373   -0.5032 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8573   -2.1608   -1.4956 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9893   -1.2470   -0.3413 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5333   -2.0388    0.2663 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6405   -2.3646    0.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3414   -2.2280    0.5733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5971   -1.3239    0.2099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5572    0.9672    2.2109 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0210   -0.7561    2.4225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5501   -1.2367    2.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6986   -2.2888    0.4722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7046   -0.3001   -1.6832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8878    0.6859   -3.1960 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8365    4.1182   -1.0137 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4095    3.3633   -1.4018 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0452    3.8738    0.3332 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6734    1.8425   -0.8203 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
 21 22  1  0
 20 23  2  0
 23  3  1  0
 18  7  1  0
 17 10  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  5 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
 11 32  1  0
 13 33  1  0
 14 34  1  0
 16 35  1  0
 22 36  1  0
 22 37  1  0
 22 38  1  0
 23 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5,7-Dihydroxy-2',4'-dimethoxyisoflavanone	ChEBI

Chemical Formula

C₁₇H₁₆O₆

Average Molecular Weight

316.3053

Monoisotopic Molecular Weight

316.094688244

IUPAC Name

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

Traditional Name

homoferreirin

CAS Registry Number

482-01-9

SMILES

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

InChI Identifier

InChI=1S/C17H16O6/c1-21-10-3-4-11(14(7-10)22-2)12-8-23-15-6-9(18)5-13(19)16(15)17(12)20/h3-7,12,18-19H,8H2,1-2H3

InChI Key

LMLDNMHDNFCNCW-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

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dimethoxyflavanone (CHEBI:5754 )
dihydroxyflavanone (CHEBI:5754 )
Isoflavonoids (C10457 )
Isoflavonoids (LMPK12050502 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0030111)
Cell membrane (HMDB: HMDB0030111)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030111)

Source

Endogenous

Endogenous (HMDB: HMDB0030111)

Plant

Plant (HMDB: HMDB0030111)
Fabaceae (HMDB: HMDB0030111)

Exogenous

Food

Food (HMDB: HMDB0030111)

Pulse

Pea

Chickpea (FooDB: FOOD00047)

Pulses (FooDB: FOOD00867)

Exogenous (HMDB: HMDB0030111)

Process

Not Available

Role

Industrial application

Agriculture

Pesticide

Fungicide (HMDB: HMDB0030111)

Pesticide (HMDB: HMDB0030111)

Biological role

Phytoalexin (HMDB: HMDB0030111)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	168 - 169 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	62.2 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	0.075 g/L	ALOGPS
logP	2.79	ALOGPS
logP	2.72	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	7.91	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.22 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	82.62 m³·mol⁻¹	ChemAxon
Polarizability	31.55 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]+	175.225	31661259
DarkChem	[M-H]-	176.893	31661259
DeepCCS	[M+H]+	171.624	30932474
DeepCCS	[M-H]-	169.266	30932474
DeepCCS	[M-2H]-	202.504	30932474
DeepCCS	[M+Na]+	177.873	30932474
AllCCS	[M+H]+	173.7	32859911
AllCCS	[M+H-H2O]+	170.2	32859911
AllCCS	[M+NH4]+	177.0	32859911
AllCCS	[M+Na]+	177.9	32859911
AllCCS	[M-H]-	176.3	32859911
AllCCS	[M+Na-2H]-	175.9	32859911
AllCCS	[M+HCOO]-	175.7	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	13.6153 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.19 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2347.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	308.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	163.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	178.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	186.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	648.9 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	682.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	89.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1183.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	476.2 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	1472.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	404.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	425.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	367.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	173.0 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	88.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Homoferreirin	COC1=CC(OC)=C(C=C1)C1COC2=CC(O)=CC(O)=C2C1=O	4140.5	Standard polar	33892256
Homoferreirin	COC1=CC(OC)=C(C=C1)C1COC2=CC(O)=CC(O)=C2C1=O	2909.9	Standard non polar	33892256
Homoferreirin	COC1=CC(OC)=C(C=C1)C1COC2=CC(O)=CC(O)=C2C1=O	2969.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Homoferreirin,1TMS,isomer #1	COC1=CC=C(C2COC3=CC(O[Si](C)(C)C)=CC(O)=C3C2=O)C(OC)=C1	2834.8	Semi standard non polar	33892256
Homoferreirin,1TMS,isomer #2	COC1=CC=C(C2COC3=CC(O)=CC(O[Si](C)(C)C)=C3C2=O)C(OC)=C1	2889.7	Semi standard non polar	33892256
Homoferreirin,2TMS,isomer #1	COC1=CC=C(C2COC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C2=O)C(OC)=C1	2781.8	Semi standard non polar	33892256
Homoferreirin,1TBDMS,isomer #1	COC1=CC=C(C2COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C2=O)C(OC)=C1	3085.7	Semi standard non polar	33892256
Homoferreirin,1TBDMS,isomer #2	COC1=CC=C(C2COC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C(OC)=C1	3144.4	Semi standard non polar	33892256
Homoferreirin,2TBDMS,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(OC)=C1	3284.9	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 - Homoferreirin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f79-0972000000-bfa02d0e32278d468d89	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Homoferreirin GC-MS (2 TMS) - 70eV, Positive	splash10-01vt-2934500000-7a4fdfeb18c01d5ea7fc	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Homoferreirin 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 - Homoferreirin 10V, Positive-QTOF	splash10-014i-0339000000-346adbec090026b60fb2	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homoferreirin 20V, Positive-QTOF	splash10-0gb9-0965000000-a080c8063d4336811742	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homoferreirin 40V, Positive-QTOF	splash10-0udr-1910000000-acafbcb1364ca94d420c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homoferreirin 10V, Negative-QTOF	splash10-014i-0019000000-a7359d4c2115c453ca7d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homoferreirin 20V, Negative-QTOF	splash10-014j-0796000000-c62eb664a6f0f81108f6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homoferreirin 40V, Negative-QTOF	splash10-0a5i-6940000000-6d81a8f3c9ef6685c79b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homoferreirin 10V, Negative-QTOF	splash10-014i-0109000000-509124d16308cc2ca18f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homoferreirin 20V, Negative-QTOF	splash10-016s-0698000000-029dec21dabef44de6b7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homoferreirin 40V, Negative-QTOF	splash10-0gk9-1490000000-650847b22ef19db39cc4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homoferreirin 10V, Positive-QTOF	splash10-014i-0309000000-eed2ffdf6fb812f81994	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homoferreirin 20V, Positive-QTOF	splash10-0gc9-0902000000-27a42f57801763de67af	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homoferreirin 40V, Positive-QTOF	splash10-0udi-0910000000-217f6e98d9210e7a3ed5	2021-09-24	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

442788

PDB ID

Not Available

ChEBI ID

5754

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1817131

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 Homoferreirin (HMDB0030111)

MOL for HMDB0030111 (Homoferreirin)

3D MOL for HMDB0030111 (Homoferreirin)

3D SDF for HMDB0030111 (Homoferreirin)

3D-SDF for HMDB0030111 (Homoferreirin)

PDB for HMDB0030111 (Homoferreirin)

3D PDB for HMDB0030111 (Homoferreirin)

SMILES for HMDB0030111 (Homoferreirin)

INCHI for HMDB0030111 (Homoferreirin)

Structure for HMDB0030111 (Homoferreirin)

3D Structure for HMDB0030111 (Homoferreirin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra