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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:37:25 UTC

Update Date

2022-03-07 02:52:35 UTC

HMDB ID

HMDB0030526

Secondary Accession Numbers

HMDB30526

Metabolite Identification

Common Name

Isovestitol

Description

Isovestitol 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, isovestitol is considered to be a flavonoid. Isovestitol has been detected, but not quantified in, hyacinth beans (Lablab purpureus) and pulses. This could make isovestitol a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Isovestitol.

Structure

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

HMDB0030526
     RDKit          3D
Isovestitol
 36 38  0  0  0  0  0  0  0  0999 V2000
   -3.4794   -2.7602   -0.1580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4072   -1.8329   -0.1614 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5265   -0.4833   -0.0448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7880    0.0327    0.1151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0338    1.4100    0.2328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3114    1.8908    0.3987 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8816    2.2232    0.1695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6164    1.6678    0.0077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3855    0.3136   -0.1018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0628   -0.3275   -0.1305 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6634   -0.0236   -1.4365 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8789   -0.8642   -1.3478 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7880   -0.4579   -0.3810 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1123   -0.6623   -0.6031 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0324   -0.2421    0.3451 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3762   -0.4553    0.1241 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5268    0.3837    1.4996 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1746    0.5689    1.6846 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2633    0.1369    0.7270 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8088    0.2661    0.9654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7179   -3.1834    0.7952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1936   -3.5698   -0.8803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3472   -2.2679   -0.6498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6816   -0.5675    0.1855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8800    2.1251   -0.4425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0734    3.2835    0.2632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7815    2.3938   -0.0137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1360   -1.4080   -0.0035 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1062   -0.5458   -2.2977 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8557    0.9778   -1.7088 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5086   -1.1720   -1.4814 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9377    0.2590   -0.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2579    0.7357    2.2419 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8538    1.0842    2.5586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078   -0.2818    1.9490 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5517    1.3526    1.0803 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  2  0
 19 20  1  0
  9  3  1  0
 20 10  1  0
 19 13  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 14 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 20 35  1  0
 20 36  1  0
M  END


  Mrv0541 05061305182D          

 20 22  0  0  0  0            999 V2000
    4.2868   -1.6500    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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    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
    2.8579    0.0000    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
    5.7158    0.0000    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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -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
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    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
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    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   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  5  4  2  0  0  0  0
 10  2  1  0  0  0  0
 10  6  1  0  0  0  0
 11  6  1  0  0  0  0
 11  9  1  0  0  0  0
 12  3  1  0  0  0  0
 12  7  2  0  0  0  0
 13  4  1  0  0  0  0
 13  8  2  0  0  0  0
 14  5  1  0  0  0  0
 14 11  1  0  0  0  0
 15  7  1  0  0  0  0
 15 10  2  0  0  0  0
 16  8  1  0  0  0  0
 16 14  2  0  0  0  0
 17 12  1  0  0  0  0
 18 13  1  0  0  0  0
 19  1  1  0  0  0  0
 19 16  1  0  0  0  0
 20  9  1  0  0  0  0
 20 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030526

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(C=CC(O)=C1)C1COC2=C(C1)C=CC(O)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O4/c1-19-16-8-13(18)4-5-14(16)11-6-10-2-3-12(17)7-15(10)20-9-11/h2-5,7-8,11,17-18H,6,9H2,1H3

> <INCHI_KEY>
FFDNYMAHNWBKCH-UHFFFAOYSA-N

> <FORMULA>
C16H16O4

> <MOLECULAR_WEIGHT>
272.2958

> <EXACT_MASS>
272.104859

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
29.062652238540494

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.93

> <JCHEM_LOGP>
3.0340066116666664

> <ALOGPS_LOGS>
-3.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.050560759699131

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.4456766572023

> <JCHEM_PKA_STRONGEST_BASIC>
-4.547089480394376

> <JCHEM_POLAR_SURFACE_AREA>
58.92

> <JCHEM_REFRACTIVITY>
75.42340000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.87e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isovestitol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030526
     RDKit          3D
Isovestitol
 36 38  0  0  0  0  0  0  0  0999 V2000
   -3.4794   -2.7602   -0.1580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4072   -1.8329   -0.1614 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5265   -0.4833   -0.0448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7880    0.0327    0.1151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0338    1.4100    0.2328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3114    1.8908    0.3987 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8816    2.2232    0.1695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6164    1.6678    0.0077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3855    0.3136   -0.1018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0628   -0.3275   -0.1305 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6634   -0.0236   -1.4365 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8789   -0.8642   -1.3478 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7880   -0.4579   -0.3810 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1123   -0.6623   -0.6031 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0324   -0.2421    0.3451 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3762   -0.4553    0.1241 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5268    0.3837    1.4996 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1746    0.5689    1.6846 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2633    0.1369    0.7270 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8088    0.2661    0.9654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7179   -3.1834    0.7952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1936   -3.5698   -0.8803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3472   -2.2679   -0.6498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6816   -0.5675    0.1855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8800    2.1251   -0.4425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0734    3.2835    0.2632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7815    2.3938   -0.0137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1360   -1.4080   -0.0035 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1062   -0.5458   -2.2977 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8557    0.9778   -1.7088 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5086   -1.1720   -1.4814 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9377    0.2590   -0.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2579    0.7357    2.2419 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8538    1.0842    2.5586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078   -0.2818    1.9490 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5517    1.3526    1.0803 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  2  0
 19 20  1  0
  9  3  1  0
 20 10  1  0
 19 13  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 14 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 20 35  1  0
 20 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  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002   0.000   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       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2    3   10                                                       
CONECT    3    2   12                                                       
CONECT    4    5   13                                                       
CONECT    5    4   14                                                       
CONECT    6   10   11                                                       
CONECT    7   12   15                                                       
CONECT    8   13   16                                                       
CONECT    9   11   20                                                       
CONECT   10    2    6   15                                                  
CONECT   11    6    9   14                                                  
CONECT   12    3    7   17                                                  
CONECT   13    4    8   18                                                  
CONECT   14    5   11   16                                                  
CONECT   15    7   10   20                                                  
CONECT   16    8   14   19                                                  
CONECT   17   12                                                            
CONECT   18   13                                                            
CONECT   19    1   16                                                       
CONECT   20    9   15                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0030526
HETATM    1  C1  UNL     1      -3.479  -2.760  -0.158  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.407  -1.833  -0.161  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.526  -0.483  -0.045  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.788   0.033   0.115  1.00  0.00           C  
HETATM    5  C4  UNL     1      -4.034   1.410   0.233  1.00  0.00           C  
HETATM    6  O2  UNL     1      -5.311   1.891   0.399  1.00  0.00           O  
HETATM    7  C5  UNL     1      -2.882   2.223   0.169  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.616   1.668   0.008  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.385   0.314  -0.102  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.063  -0.328  -0.131  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.663  -0.024  -1.436  1.00  0.00           C  
HETATM   12  O3  UNL     1       1.879  -0.864  -1.348  1.00  0.00           O  
HETATM   13  C10 UNL     1       2.788  -0.458  -0.381  1.00  0.00           C  
HETATM   14  C11 UNL     1       4.112  -0.662  -0.603  1.00  0.00           C  
HETATM   15  C12 UNL     1       5.032  -0.242   0.345  1.00  0.00           C  
HETATM   16  O4  UNL     1       6.376  -0.455   0.124  1.00  0.00           O  
HETATM   17  C13 UNL     1       4.527   0.384   1.500  1.00  0.00           C  
HETATM   18  C14 UNL     1       3.175   0.569   1.685  1.00  0.00           C  
HETATM   19  C15 UNL     1       2.263   0.137   0.727  1.00  0.00           C  
HETATM   20  C16 UNL     1       0.809   0.266   0.965  1.00  0.00           C  
HETATM   21  H1  UNL     1      -3.718  -3.183   0.795  1.00  0.00           H  
HETATM   22  H2  UNL     1      -3.194  -3.570  -0.880  1.00  0.00           H  
HETATM   23  H3  UNL     1      -4.347  -2.268  -0.650  1.00  0.00           H  
HETATM   24  H4  UNL     1      -4.682  -0.567   0.186  1.00  0.00           H  
HETATM   25  H5  UNL     1      -5.880   2.125  -0.442  1.00  0.00           H  
HETATM   26  H6  UNL     1      -3.073   3.283   0.263  1.00  0.00           H  
HETATM   27  H7  UNL     1      -0.782   2.394  -0.014  1.00  0.00           H  
HETATM   28  H8  UNL     1      -0.136  -1.408  -0.004  1.00  0.00           H  
HETATM   29  H9  UNL     1       0.106  -0.546  -2.298  1.00  0.00           H  
HETATM   30  H10 UNL     1       0.856   0.978  -1.709  1.00  0.00           H  
HETATM   31  H11 UNL     1       4.509  -1.172  -1.481  1.00  0.00           H  
HETATM   32  H12 UNL     1       6.938   0.259  -0.372  1.00  0.00           H  
HETATM   33  H13 UNL     1       5.258   0.736   2.242  1.00  0.00           H  
HETATM   34  H14 UNL     1       2.854   1.084   2.559  1.00  0.00           H  
HETATM   35  H15 UNL     1       0.608  -0.282   1.949  1.00  0.00           H  
HETATM   36  H16 UNL     1       0.552   1.353   1.080  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3
CONECT    3    4    4    9
CONECT    4    5   24
CONECT    5    6    7    7
CONECT    6   25
CONECT    7    8   26
CONECT    8    9    9   27
CONECT    9   10
CONECT   10   11   20   28
CONECT   11   12   29   30
CONECT   12   13
CONECT   13   14   14   19
CONECT   14   15   31
CONECT   15   16   17   17
CONECT   16   32
CONECT   17   18   33
CONECT   18   19   19   34
CONECT   19   20
CONECT   20   35   36
END

HMDB0030526
     RDKit          3D
Isovestitol
 36 38  0  0  0  0  0  0  0  0999 V2000
   -3.4794   -2.7602   -0.1580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4072   -1.8329   -0.1614 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5265   -0.4833   -0.0448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7880    0.0327    0.1151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0338    1.4100    0.2328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3114    1.8908    0.3987 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8816    2.2232    0.1695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6164    1.6678    0.0077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3855    0.3136   -0.1018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0628   -0.3275   -0.1305 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6634   -0.0236   -1.4365 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8789   -0.8642   -1.3478 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7880   -0.4579   -0.3810 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1123   -0.6623   -0.6031 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0324   -0.2421    0.3451 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3762   -0.4553    0.1241 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5268    0.3837    1.4996 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1746    0.5689    1.6846 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2633    0.1369    0.7270 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8088    0.2661    0.9654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7179   -3.1834    0.7952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1936   -3.5698   -0.8803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3472   -2.2679   -0.6498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6816   -0.5675    0.1855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8800    2.1251   -0.4425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0734    3.2835    0.2632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7815    2.3938   -0.0137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1360   -1.4080   -0.0035 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1062   -0.5458   -2.2977 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8557    0.9778   -1.7088 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5086   -1.1720   -1.4814 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9377    0.2590   -0.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2579    0.7357    2.2419 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8538    1.0842    2.5586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078   -0.2818    1.9490 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5517    1.3526    1.0803 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  2  0
 19 20  1  0
  9  3  1  0
 20 10  1  0
 19 13  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 14 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 20 35  1  0
 20 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4',7-Dihydroxy-2'-methoxyisoflavan	HMDB
7,4'-Dihydroxy-2'-methoxyisoflavan	HMDB

Chemical Formula

C₁₆H₁₆O₄

Average Molecular Weight

272.2958

Monoisotopic Molecular Weight

272.104859

IUPAC Name

3-(4-hydroxy-2-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol

Traditional Name

isovestitol

CAS Registry Number

63631-42-5

SMILES

COC1=C(C=CC(O)=C1)C1COC2=C(C1)C=CC(O)=C2

InChI Identifier

InChI=1S/C16H16O4/c1-19-16-8-13(18)4-5-14(16)11-6-10-2-3-12(17)7-15(10)20-9-11/h2-5,7-8,11,17-18H,6,9H2,1H3

InChI Key

FFDNYMAHNWBKCH-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
Hydroxyisoflavonoid
Isoflavanol
Isoflavan
Chromane
Benzopyran
Methoxyphenol
1-benzopyran
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Oxacycle
Ether
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Isoflavans (LMPK12080028 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0030526)

Cellular substructure

Membrane (HMDB: HMDB0030526)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030526)

Source

Endogenous

Endogenous (HMDB: HMDB0030526)

Plant

Plant (HMDB: HMDB0030526)
Fabaceae (HMDB: HMDB0030526)

Exogenous

Food

Food (HMDB: HMDB0030526)

Pulse

Bean

Hyacinth bean (FooDB: FOOD00381)

Pulses (FooDB: FOOD00867)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	95 - 97 °C	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
Water Solubility	0.049 g/L	ALOGPS
logP	2.93	ALOGPS
logP	3.03	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	9.45	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.92 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	75.42 m³·mol⁻¹	ChemAxon
Polarizability	29.06 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]+	164.109	31661259
DarkChem	[M-H]-	164.834	31661259
DeepCCS	[M+H]+	167.861	30932474
DeepCCS	[M-H]-	165.503	30932474
DeepCCS	[M-2H]-	198.39	30932474
DeepCCS	[M+Na]+	173.955	30932474
AllCCS	[M+H]+	163.6	32859911
AllCCS	[M+H-H2O]+	159.8	32859911
AllCCS	[M+NH4]+	167.1	32859911
AllCCS	[M+Na]+	168.1	32859911
AllCCS	[M-H]-	167.3	32859911
AllCCS	[M+Na-2H]-	166.8	32859911
AllCCS	[M+HCOO]-	166.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isovestitol	COC1=C(C=CC(O)=C1)C1COC2=C(C1)C=CC(O)=C2	3537.2	Standard polar	33892256
Isovestitol	COC1=C(C=CC(O)=C1)C1COC2=C(C1)C=CC(O)=C2	2543.3	Standard non polar	33892256
Isovestitol	COC1=C(C=CC(O)=C1)C1COC2=C(C1)C=CC(O)=C2	2795.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Isovestitol,1TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=CC=C1C1COC2=CC(O)=CC=C2C1	2633.7	Semi standard non polar	33892256
Isovestitol,1TMS,isomer #2	COC1=CC(O)=CC=C1C1COC2=CC(O[Si](C)(C)C)=CC=C2C1	2614.8	Semi standard non polar	33892256
Isovestitol,2TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=CC=C1C1COC2=CC(O[Si](C)(C)C)=CC=C2C1	2573.1	Semi standard non polar	33892256
Isovestitol,1TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1C1COC2=CC(O)=CC=C2C1	2907.2	Semi standard non polar	33892256
Isovestitol,1TBDMS,isomer #2	COC1=CC(O)=CC=C1C1COC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C2C1	2899.9	Semi standard non polar	33892256
Isovestitol,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=C2C1	3044.2	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 - Isovestitol GC-MS (Non-derivatized) - 70eV, Positive	splash10-059f-0690000000-180d1c96f0e9bc8713d7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isovestitol GC-MS (2 TMS) - 70eV, Positive	splash10-0ukc-6538900000-4316f5d92e1fd25e580d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isovestitol 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 - Isovestitol 10V, Positive-QTOF	splash10-00di-0890000000-6c99ad5a8e9d09ab2422	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isovestitol 20V, Positive-QTOF	splash10-00di-0940000000-bd9f4a7c26e8f861f365	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isovestitol 40V, Positive-QTOF	splash10-05fr-2910000000-fcfe5da69108544cc238	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isovestitol 10V, Negative-QTOF	splash10-00di-0390000000-bf9a85e085a3328f2939	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isovestitol 20V, Negative-QTOF	splash10-00di-1790000000-da31b3a869ecec22f731	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isovestitol 40V, Negative-QTOF	splash10-00di-4920000000-bd600dee7576d197bbaf	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isovestitol 10V, Positive-QTOF	splash10-00di-0590000000-205914e7aafe43d0c557	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isovestitol 20V, Positive-QTOF	splash10-00dj-0790000000-9a717852d6eb26423768	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isovestitol 40V, Positive-QTOF	splash10-00dj-0910000000-d50600b78c3cf36c56f1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isovestitol 10V, Negative-QTOF	splash10-00di-0090000000-bd72d08856f9fcdba210	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isovestitol 20V, Negative-QTOF	splash10-00xr-0490000000-65d79fac9fcb3bd4232c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isovestitol 40V, Negative-QTOF	splash10-05n3-4960000000-027c0a9c4560e0619424	2021-09-23	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

FDB002398

KNApSAcK ID

C00009709

Chemspider ID

514489

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

591830

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Isovestitol (HMDB0030526)

MOL for HMDB0030526 (Isovestitol)

3D MOL for HMDB0030526 (Isovestitol)

3D SDF for HMDB0030526 (Isovestitol)

3D-SDF for HMDB0030526 (Isovestitol)

PDB for HMDB0030526 (Isovestitol)

3D PDB for HMDB0030526 (Isovestitol)

SMILES for HMDB0030526 (Isovestitol)

INCHI for HMDB0030526 (Isovestitol)

Structure for HMDB0030526 (Isovestitol)

3D Structure for HMDB0030526 (Isovestitol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra