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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 03:50:19 UTC

Update Date

2021-09-23 03:50:19 UTC

HMDB ID

HMDB0301940

Secondary Accession Numbers

None

Metabolite Identification

Common Name

5-O-Methylgenistein

Description

5-o-methylgenistein is a member of the class of compounds known as isoflavones. Isoflavones are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom. Thus, 5-o-methylgenistein is considered to be a flavonoid lipid molecule. 5-o-methylgenistein is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 5-o-methylgenistein can be found in scarlet bean, which makes 5-o-methylgenistein a potential biomarker for the consumption of this food product.

Structure

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

HMDB0301940
     RDKit          3D
5-O-Methylgenistein
 33 35  0  0  0  0  0  0  0  0999 V2000
   -3.2302    2.7132    1.1069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2898    1.7721    0.7127 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5509    0.5643    0.1013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8362    0.1529   -0.1929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0153   -1.0695   -0.8056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3189   -1.5007   -1.1109 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9613   -1.8942   -1.1346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6877   -1.4594   -0.8297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6645   -2.2082   -1.1236 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5662   -1.8386   -0.8538 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8630   -0.6377   -0.2432 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2616   -0.2615    0.0418 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7355    1.0042   -0.2320 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0538    1.3227    0.0484 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9206    0.3978    0.6018 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2479    0.7056    0.8883 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4482   -0.8666    0.8756 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1487   -1.1630    0.5935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1867    0.1926    0.0888 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0079    1.3018    0.6470 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4645   -0.2324   -0.2116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3258    3.5409    0.3447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2370    2.3438    1.2886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9204    3.2562    2.0460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7020    0.7865    0.0557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4777   -2.3911   -1.5592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1102   -2.8548   -1.6166 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4334   -2.4675   -1.1001 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0690    1.7279   -0.6616 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4519    2.3064   -0.1557 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9370    0.5424    0.1636 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0841   -1.6240    1.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7502   -2.1622    0.8025 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 11 19  1  0
 19 20  2  0
 19 21  1  0
 21  3  1  0
 21  8  2  0
 18 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
  7 27  1  0
 10 28  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
M  END


  Mrv0541 02241220452D          

 21 23  0  0  0  0            999 V2000
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    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
   -1.4289   -1.6500    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   -2.8875    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
   -3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
  8 14  1  0  0  0  0
  4 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
  3 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0301940

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(O)=CC2=C1C(=O)C(=CO2)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O5/c1-20-13-6-11(18)7-14-15(13)16(19)12(8-21-14)9-2-4-10(17)5-3-9/h2-8,17-18H,1H3

> <INCHI_KEY>
YSINCDVRUMTOPK-UHFFFAOYSA-N

> <FORMULA>
C16H12O5

> <MOLECULAR_WEIGHT>
284.2635

> <EXACT_MASS>
284.068473494

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
28.534234679734016

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-hydroxy-3-(4-hydroxyphenyl)-5-methoxy-4H-chromen-4-one

> <ALOGPS_LOGP>
3.35

> <JCHEM_LOGP>
2.5727664456666663

> <ALOGPS_LOGS>
-3.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.960078645481795

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.542611577394699

> <JCHEM_PKA_STRONGEST_BASIC>
-4.766230649544202

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
76.1652

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.67e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-O-methylgenistein

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0301940
     RDKit          3D
5-O-Methylgenistein
 33 35  0  0  0  0  0  0  0  0999 V2000
   -3.2302    2.7132    1.1069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2898    1.7721    0.7127 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5509    0.5643    0.1013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8362    0.1529   -0.1929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0153   -1.0695   -0.8056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3189   -1.5007   -1.1109 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9613   -1.8942   -1.1346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6877   -1.4594   -0.8297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6645   -2.2082   -1.1236 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5662   -1.8386   -0.8538 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8630   -0.6377   -0.2432 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2616   -0.2615    0.0418 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7355    1.0042   -0.2320 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0538    1.3227    0.0484 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9206    0.3978    0.6018 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2479    0.7056    0.8883 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4482   -0.8666    0.8756 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1487   -1.1630    0.5935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1867    0.1926    0.0888 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0079    1.3018    0.6470 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4645   -0.2324   -0.2116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3258    3.5409    0.3447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2370    2.3438    1.2886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9204    3.2562    2.0460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7020    0.7865    0.0557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4777   -2.3911   -1.5592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1102   -2.8548   -1.6166 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4334   -2.4675   -1.1001 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0690    1.7279   -0.6616 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4519    2.3064   -0.1557 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9370    0.5424    0.1636 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0841   -1.6240    1.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7502   -2.1622    0.8025 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 11 19  1  0
 19 20  2  0
 19 21  1  0
 21  3  1  0
 21  8  2  0
 18 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
  7 27  1  0
 10 28  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -5.335  -3.080   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       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4   19                                                  
CONECT    4    3    5   15                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    2    8                                                  
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    8                                                       
CONECT   15    4   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18    3   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0301940
HETATM    1  C1  UNL     1      -3.230   2.713   1.107  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.290   1.772   0.713  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.551   0.564   0.101  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.836   0.153  -0.193  1.00  0.00           C  
HETATM    5  C4  UNL     1      -4.015  -1.069  -0.806  1.00  0.00           C  
HETATM    6  O2  UNL     1      -5.319  -1.501  -1.111  1.00  0.00           O  
HETATM    7  C5  UNL     1      -2.961  -1.894  -1.135  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.688  -1.459  -0.830  1.00  0.00           C  
HETATM    9  O3  UNL     1      -0.664  -2.208  -1.124  1.00  0.00           O  
HETATM   10  C7  UNL     1       0.566  -1.839  -0.854  1.00  0.00           C  
HETATM   11  C8  UNL     1       0.863  -0.638  -0.243  1.00  0.00           C  
HETATM   12  C9  UNL     1       2.262  -0.262   0.042  1.00  0.00           C  
HETATM   13  C10 UNL     1       2.736   1.004  -0.232  1.00  0.00           C  
HETATM   14  C11 UNL     1       4.054   1.323   0.048  1.00  0.00           C  
HETATM   15  C12 UNL     1       4.921   0.398   0.602  1.00  0.00           C  
HETATM   16  O4  UNL     1       6.248   0.706   0.888  1.00  0.00           O  
HETATM   17  C13 UNL     1       4.448  -0.867   0.876  1.00  0.00           C  
HETATM   18  C14 UNL     1       3.149  -1.163   0.594  1.00  0.00           C  
HETATM   19  C15 UNL     1      -0.187   0.193   0.089  1.00  0.00           C  
HETATM   20  O5  UNL     1       0.008   1.302   0.647  1.00  0.00           O  
HETATM   21  C16 UNL     1      -1.465  -0.232  -0.212  1.00  0.00           C  
HETATM   22  H1  UNL     1      -3.326   3.541   0.345  1.00  0.00           H  
HETATM   23  H2  UNL     1      -4.237   2.344   1.289  1.00  0.00           H  
HETATM   24  H3  UNL     1      -2.920   3.256   2.046  1.00  0.00           H  
HETATM   25  H4  UNL     1      -4.702   0.786   0.056  1.00  0.00           H  
HETATM   26  H5  UNL     1      -5.478  -2.391  -1.559  1.00  0.00           H  
HETATM   27  H6  UNL     1      -3.110  -2.855  -1.617  1.00  0.00           H  
HETATM   28  H7  UNL     1       1.433  -2.467  -1.100  1.00  0.00           H  
HETATM   29  H8  UNL     1       2.069   1.728  -0.662  1.00  0.00           H  
HETATM   30  H9  UNL     1       4.452   2.306  -0.156  1.00  0.00           H  
HETATM   31  H10 UNL     1       6.937   0.542   0.164  1.00  0.00           H  
HETATM   32  H11 UNL     1       5.084  -1.624   1.307  1.00  0.00           H  
HETATM   33  H12 UNL     1       2.750  -2.162   0.802  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4   21
CONECT    4    5   25
CONECT    5    6    7    7
CONECT    6   26
CONECT    7    8   27
CONECT    8    9   21   21
CONECT    9   10
CONECT   10   11   11   28
CONECT   11   12   19
CONECT   12   13   13   18
CONECT   13   14   29
CONECT   14   15   15   30
CONECT   15   16   17
CONECT   16   31
CONECT   17   18   18   32
CONECT   18   33
CONECT   19   20   20   21
END

HMDB0301940
     RDKit          3D
5-O-Methylgenistein
 33 35  0  0  0  0  0  0  0  0999 V2000
   -3.2302    2.7132    1.1069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2898    1.7721    0.7127 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5509    0.5643    0.1013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8362    0.1529   -0.1929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0153   -1.0695   -0.8056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3189   -1.5007   -1.1109 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9613   -1.8942   -1.1346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6877   -1.4594   -0.8297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6645   -2.2082   -1.1236 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5662   -1.8386   -0.8538 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8630   -0.6377   -0.2432 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2616   -0.2615    0.0418 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7355    1.0042   -0.2320 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0538    1.3227    0.0484 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9206    0.3978    0.6018 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2479    0.7056    0.8883 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4482   -0.8666    0.8756 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1487   -1.1630    0.5935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1867    0.1926    0.0888 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0079    1.3018    0.6470 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4645   -0.2324   -0.2116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3258    3.5409    0.3447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2370    2.3438    1.2886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9204    3.2562    2.0460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7020    0.7865    0.0557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4777   -2.3911   -1.5592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1102   -2.8548   -1.6166 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4334   -2.4675   -1.1001 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0690    1.7279   -0.6616 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4519    2.3064   -0.1557 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9370    0.5424    0.1636 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0841   -1.6240    1.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7502   -2.1622    0.8025 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 11 19  1  0
 19 20  2  0
 19 21  1  0
 21  3  1  0
 21  8  2  0
 18 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
  7 27  1  0
 10 28  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₆H₁₂O₅

Average Molecular Weight

284.2635

Monoisotopic Molecular Weight

284.068473494

IUPAC Name

7-hydroxy-3-(4-hydroxyphenyl)-5-methoxy-4H-chromen-4-one

Traditional Name

5-O-methylgenistein

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=CC2=C1C(=O)C(=CO2)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C16H12O5/c1-20-13-6-11(18)7-14-15(13)16(19)12(8-21-14)9-2-4-10(17)5-3-9/h2-8,17-18H,1H3

InChI Key

YSINCDVRUMTOPK-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflav-2-enes

Direct Parent

Isoflavones

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Isoflavonoids (LMPK12050338 )

Ontology

Not Available

Exogenous (HMDB: HMDB0301940)

Food

Pulse

Bean

Scarlet bean (FooDB: FOOD00132)

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	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	3.35	ALOGPS
logP	2.57	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	6.54	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	76.17 m³·mol⁻¹	ChemAxon
Polarizability	28.53 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
AllCCS	[M+H]+	164.587	32859911
AllCCS	[M+H-H2O]+	160.786	32859911
AllCCS	[M+Na]+	169.134	32859911
AllCCS	[M+NH4]+	168.118	32859911
AllCCS	[M-H]-	166.19	32859911
AllCCS	[M+Na-2H]-	165.44	32859911
AllCCS	[M+HCOO]-	164.747	32859911
DeepCCS	[M+H]+	169.327	30932474
DeepCCS	[M-H]-	166.969	30932474
DeepCCS	[M-2H]-	199.978	30932474
DeepCCS	[M+Na]+	175.42	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	11.4521 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.13 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1981.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	287.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	153.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	176.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	378.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	487.0 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	487.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	118.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1001.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	372.0 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	1251.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	341.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	342.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	367.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	286.1 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	75.1 seconds	40023050

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-O-Methylgenistein 10V, Positive-QTOF	splash10-000i-0090000000-23303322ebea0f056c7b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-O-Methylgenistein 20V, Positive-QTOF	splash10-000i-0090000000-5ee04a63348d0898fa46	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-O-Methylgenistein 40V, Positive-QTOF	splash10-0v4i-3590000000-b9792ca23f8c6952c1f2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-O-Methylgenistein 10V, Negative-QTOF	splash10-001i-0090000000-a367cc1f64d4f0118343	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-O-Methylgenistein 20V, Negative-QTOF	splash10-001i-0090000000-ecf858e54ec64d797782	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-O-Methylgenistein 40V, Negative-QTOF	splash10-0gb9-4980000000-64bc80468d0e8822d713	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-O-Methylgenistein 10V, Positive-QTOF	splash10-000i-0090000000-edc9ea273e98ea6aa00a	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-O-Methylgenistein 20V, Positive-QTOF	splash10-000i-0090000000-edc9ea273e98ea6aa00a	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-O-Methylgenistein 40V, Positive-QTOF	splash10-0ar3-0490000000-d49cad46d867a185d903	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-O-Methylgenistein 10V, Negative-QTOF	splash10-001i-0090000000-549f6b30f75977e8ff35	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-O-Methylgenistein 20V, Negative-QTOF	splash10-001i-0090000000-9e3bf65af5857209aca6	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-O-Methylgenistein 40V, Negative-QTOF	splash10-0fi0-0290000000-afe2a4c414babf34838b	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

FDB001650

KNApSAcK ID

C00009452

Chemspider ID

4678012

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5748551

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 5-O-Methylgenistein (HMDB0301940)

MOL for HMDB0301940 (5-O-Methylgenistein)

3D MOL for HMDB0301940 (5-O-Methylgenistein)

3D SDF for HMDB0301940 (5-O-Methylgenistein)

3D-SDF for HMDB0301940 (5-O-Methylgenistein)

PDB for HMDB0301940 (5-O-Methylgenistein)

3D PDB for HMDB0301940 (5-O-Methylgenistein)

SMILES for HMDB0301940 (5-O-Methylgenistein)

INCHI for HMDB0301940 (5-O-Methylgenistein)

Structure for HMDB0301940 (5-O-Methylgenistein)

3D Structure for HMDB0301940 (5-O-Methylgenistein)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

MS/MS Spectra