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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 23:56:34 UTC

Update Date

2021-09-23 23:56:34 UTC

HMDB ID

HMDB0303171

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Isorhapontigenin

Description

Isorhapontigenin is a member of the class of compounds known as stilbenes. Stilbenes are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. Isorhapontigenin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Isorhapontigenin can be found in garden rhubarb, which makes isorhapontigenin a potential biomarker for the consumption of this food product. Isorhapontigenin is a tetrahydroxylated stilbenoid with a methoxy group. It is an isomer of rhapontigenin and an analog of resveratrol. It is found in the Chinese herb Gnetum cleistostachyum, in Gnetum parvifolium and in the seeds of the palm Aiphanes aculeata .

Structure

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

HMDB0303171
     RDKit          3D
Isorhapontigenin
 33 34  0  0  0  0  0  0  0  0999 V2000
    4.9600    0.9390    1.0639 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4224    0.5612   -0.1604 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1395    0.0784   -0.3632 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2796   -0.0623    0.6889 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9653   -0.5415    0.5790 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2069   -0.7897    1.7865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0513   -0.7108    1.9537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0032   -0.3166    0.9492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2884   -0.8744    1.0303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3348   -0.5030    0.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5990   -1.0664    0.3339 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1673    0.4790   -0.7138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9225    1.0555   -0.8277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6865    2.0436   -1.7608 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8559    0.6593   -0.0022 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5945   -0.8718   -0.7039 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4663   -0.7307   -1.7868 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7498   -0.2550   -1.6388 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6155   -0.1160   -2.7224 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6299    0.2078    1.8306 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0632    0.8395    1.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6372    1.9404    1.4156 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5939    0.2040    1.7000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8036   -1.0943    2.7082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4228   -0.9766    2.9791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4578   -1.6526    1.7716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3197   -0.6949    0.9437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9792    0.7915   -1.3538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4273    2.3504   -2.3670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9143    1.1700   -0.0887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3762   -1.3013   -0.9207 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1404   -0.9992   -2.7861 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5381    0.2374   -2.5410 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
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
  5 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18  3  1  0
 15  8  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  0
  9 26  1  0
 11 27  1  0
 12 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 19 33  1  0
M  END

  Mrv0541 02241210582D          

 19 20  0  0  0  0            999 V2000
    0.0008    3.0938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0008    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7143    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7143    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4293    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4293   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7143   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7143   -1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0006   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0006   -2.6813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7143   -3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7143    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7143    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0008    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4293    0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0006   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7143   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7143   -1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4293   -1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2 12  2  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4 14  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 16  2  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 18  1  0  0  0  0
 10 11  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0303171

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(\C=C/C2=CC(O)=CC(O)=C2)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O4/c1-19-15-8-10(4-5-14(15)18)2-3-11-6-12(16)9-13(17)7-11/h2-9,16-18H,1H3/b3-2-

> <INCHI_KEY>
ANNNBEZJTNCXHY-IHWYPQMZSA-N

> <FORMULA>
C15H14O4

> <MOLECULAR_WEIGHT>
258.2693

> <EXACT_MASS>
258.089208936

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
26.924818684121846

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[(Z)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]benzene-1,3-diol

> <ALOGPS_LOGP>
2.64

> <JCHEM_LOGP>
3.244719620666666

> <ALOGPS_LOGS>
-3.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.937529844511987

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.094213648115637

> <JCHEM_PKA_STRONGEST_BASIC>
-4.893862070232119

> <JCHEM_POLAR_SURFACE_AREA>
69.92

> <JCHEM_REFRACTIVITY>
73.91870000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.66e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-[(Z)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]benzene-1,3-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0303171
     RDKit          3D
Isorhapontigenin
 33 34  0  0  0  0  0  0  0  0999 V2000
    4.9600    0.9390    1.0639 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4224    0.5612   -0.1604 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1395    0.0784   -0.3632 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2796   -0.0623    0.6889 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9653   -0.5415    0.5790 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2069   -0.7897    1.7865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0513   -0.7108    1.9537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0032   -0.3166    0.9492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2884   -0.8744    1.0303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3348   -0.5030    0.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5990   -1.0664    0.3339 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1673    0.4790   -0.7138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9225    1.0555   -0.8277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6865    2.0436   -1.7608 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8559    0.6593   -0.0022 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5945   -0.8718   -0.7039 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4663   -0.7307   -1.7868 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7498   -0.2550   -1.6388 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6155   -0.1160   -2.7224 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6299    0.2078    1.8306 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0632    0.8395    1.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6372    1.9404    1.4156 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5939    0.2040    1.7000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8036   -1.0943    2.7082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4228   -0.9766    2.9791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4578   -1.6526    1.7716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3197   -0.6949    0.9437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9792    0.7915   -1.3538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4273    2.3504   -2.3670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9143    1.1700   -0.0887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3762   -1.3013   -0.9207 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1404   -0.9992   -2.7861 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5381    0.2374   -2.5410 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
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
  5 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18  3  1  0
 15  8  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  0
  9 26  1  0
 11 27  1  0
 12 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 19 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       0.001   5.775   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.001   4.235   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.333   3.465   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.333   1.925   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.668   1.155   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.668  -0.385   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.333  -1.155   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.333  -2.695   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.001  -3.465   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.001  -5.005   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.333  -5.775   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.333   3.465   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.333   1.925   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.001   1.155   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.668   1.155   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.001  -0.385   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.333  -1.155   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.333  -2.695   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.668  -3.465   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   14                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   16                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   18                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    2   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14    4   13                                                       
CONECT   15   13                                                            
CONECT   16    7   17                                                       
CONECT   17   16   18                                                       
CONECT   18    9   17   19                                                  
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0303171
HETATM    1  C1  UNL     1       4.960   0.939   1.064  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.422   0.561  -0.160  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.139   0.078  -0.363  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.280  -0.062   0.689  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.965  -0.541   0.579  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.207  -0.790   1.787  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.051  -0.711   1.954  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.003  -0.317   0.949  1.00  0.00           C  
HETATM    9  C8  UNL     1      -3.288  -0.874   1.030  1.00  0.00           C  
HETATM   10  C9  UNL     1      -4.335  -0.503   0.240  1.00  0.00           C  
HETATM   11  O2  UNL     1      -5.599  -1.066   0.334  1.00  0.00           O  
HETATM   12  C10 UNL     1      -4.167   0.479  -0.714  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.922   1.055  -0.828  1.00  0.00           C  
HETATM   14  O3  UNL     1      -2.687   2.044  -1.761  1.00  0.00           O  
HETATM   15  C12 UNL     1      -1.856   0.659  -0.002  1.00  0.00           C  
HETATM   16  C13 UNL     1       0.595  -0.872  -0.704  1.00  0.00           C  
HETATM   17  C14 UNL     1       1.466  -0.731  -1.787  1.00  0.00           C  
HETATM   18  C15 UNL     1       2.750  -0.255  -1.639  1.00  0.00           C  
HETATM   19  O4  UNL     1       3.616  -0.116  -2.722  1.00  0.00           O  
HETATM   20  H1  UNL     1       4.630   0.208   1.831  1.00  0.00           H  
HETATM   21  H2  UNL     1       6.063   0.840   1.002  1.00  0.00           H  
HETATM   22  H3  UNL     1       4.637   1.940   1.416  1.00  0.00           H  
HETATM   23  H4  UNL     1       2.594   0.204   1.700  1.00  0.00           H  
HETATM   24  H5  UNL     1       0.804  -1.094   2.708  1.00  0.00           H  
HETATM   25  H6  UNL     1      -1.423  -0.977   2.979  1.00  0.00           H  
HETATM   26  H7  UNL     1      -3.458  -1.653   1.772  1.00  0.00           H  
HETATM   27  H8  UNL     1      -6.320  -0.695   0.944  1.00  0.00           H  
HETATM   28  H9  UNL     1      -4.979   0.791  -1.354  1.00  0.00           H  
HETATM   29  H10 UNL     1      -3.427   2.350  -2.367  1.00  0.00           H  
HETATM   30  H11 UNL     1      -0.914   1.170  -0.089  1.00  0.00           H  
HETATM   31  H12 UNL     1      -0.376  -1.301  -0.921  1.00  0.00           H  
HETATM   32  H13 UNL     1       1.140  -0.999  -2.786  1.00  0.00           H  
HETATM   33  H14 UNL     1       4.538   0.237  -2.541  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3
CONECT    3    4    4   18
CONECT    4    5   23
CONECT    5    6   16   16
CONECT    6    7    7   24
CONECT    7    8   25
CONECT    8    9    9   15
CONECT    9   10   26
CONECT   10   11   12   12
CONECT   11   27
CONECT   12   13   28
CONECT   13   14   15   15
CONECT   14   29
CONECT   15   30
CONECT   16   17   31
CONECT   17   18   18   32
CONECT   18   19
CONECT   19   33
END

HMDB0303171
     RDKit          3D
Isorhapontigenin
 33 34  0  0  0  0  0  0  0  0999 V2000
    4.9600    0.9390    1.0639 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4224    0.5612   -0.1604 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1395    0.0784   -0.3632 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2796   -0.0623    0.6889 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9653   -0.5415    0.5790 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2069   -0.7897    1.7865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0513   -0.7108    1.9537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0032   -0.3166    0.9492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2884   -0.8744    1.0303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3348   -0.5030    0.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5990   -1.0664    0.3339 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1673    0.4790   -0.7138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9225    1.0555   -0.8277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6865    2.0436   -1.7608 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8559    0.6593   -0.0022 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5945   -0.8718   -0.7039 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4663   -0.7307   -1.7868 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7498   -0.2550   -1.6388 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6155   -0.1160   -2.7224 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6299    0.2078    1.8306 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0632    0.8395    1.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6372    1.9404    1.4156 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5939    0.2040    1.7000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8036   -1.0943    2.7082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4228   -0.9766    2.9791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4578   -1.6526    1.7716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3197   -0.6949    0.9437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9792    0.7915   -1.3538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4273    2.3504   -2.3670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9143    1.1700   -0.0887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3762   -1.3013   -0.9207 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1404   -0.9992   -2.7861 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5381    0.2374   -2.5410 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
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
  5 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18  3  1  0
 15  8  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  0
  9 26  1  0
 11 27  1  0
 12 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 19 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₁₄O₄

Average Molecular Weight

258.2693

Monoisotopic Molecular Weight

258.089208936

IUPAC Name

5-[(Z)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]benzene-1,3-diol

Traditional Name

5-[(Z)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]benzene-1,3-diol

CAS Registry Number

Not Available

SMILES

COC1=CC(\C=C/C2=CC(O)=CC(O)=C2)=CC=C1O

InChI Identifier

InChI=1S/C15H14O4/c1-19-15-8-10(4-5-14(15)18)2-3-11-6-12(16)9-13(17)7-11/h2-9,16-18H,1H3/b3-2-

InChI Key

ANNNBEZJTNCXHY-IHWYPQMZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Not Available

Direct Parent

Stilbenes

Alternative Parents

Substituents

Stilbene
Methoxyphenol
Anisole
Phenoxy compound
Phenol ether
Resorcinol
Styrene
Methoxybenzene
1-hydroxy-4-unsubstituted benzenoid
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Ether
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0303171)

Food

Vegetable

Stalk vegetable

Garden rhubarb (FooDB: FOOD00154)

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	2.64	ALOGPS
logP	3.24	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	9.09	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	69.92 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	73.92 m³·mol⁻¹	ChemAxon
Polarizability	26.92 Å³	ChemAxon
Number of Rings	2	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]+	158.954	32859911
AllCCS	[M+H-H2O]+	154.944	32859911
AllCCS	[M+Na]+	163.757	32859911
AllCCS	[M+NH4]+	162.683	32859911
AllCCS	[M-H]-	159.44	32859911
AllCCS	[M+Na-2H]-	159.048	32859911
AllCCS	[M+HCOO]-	158.74	32859911
DeepCCS	[M+H]+	159.713	30932474
DeepCCS	[M-H]-	157.355	30932474
DeepCCS	[M-2H]-	190.509	30932474
DeepCCS	[M+Na]+	165.806	30932474

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 - Isorhapontigenin 10V, Positive-QTOF	splash10-0a4i-0090000000-8d146302b46446b89288	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isorhapontigenin 20V, Positive-QTOF	splash10-0a4i-0490000000-d93f37ed40bb8b1d636d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isorhapontigenin 40V, Positive-QTOF	splash10-0k9i-2920000000-382f4cffe97b8e173b3a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isorhapontigenin 10V, Negative-QTOF	splash10-0a4i-0090000000-3147354735d5d663e856	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isorhapontigenin 20V, Negative-QTOF	splash10-0a4i-0090000000-69a2d2d0db6c85bdffac	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isorhapontigenin 40V, Negative-QTOF	splash10-0006-2980000000-a650e97c610e36c31f1e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isorhapontigenin 10V, Positive-QTOF	splash10-0a4i-0090000000-1e5d9345ff81c63f5d62	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isorhapontigenin 20V, Positive-QTOF	splash10-0a70-0960000000-23d1bcb901e03aa717a1	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isorhapontigenin 40V, Positive-QTOF	splash10-00ba-1920000000-2488da30d05ff64235ed	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isorhapontigenin 10V, Negative-QTOF	splash10-0a4i-0090000000-c2a50a42dfada53572a9	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isorhapontigenin 20V, Negative-QTOF	splash10-0a4l-0190000000-89e8e2812ea042369266	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isorhapontigenin 40V, Negative-QTOF	splash10-0a4i-0490000000-02d3d95119e4b70a01ce	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

FDB008478

KNApSAcK ID

Not Available

Chemspider ID

10298686

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21681009

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 Isorhapontigenin (HMDB0303171)

MOL for HMDB0303171 (Isorhapontigenin)

3D MOL for HMDB0303171 (Isorhapontigenin)

3D SDF for HMDB0303171 (Isorhapontigenin)

3D-SDF for HMDB0303171 (Isorhapontigenin)

PDB for HMDB0303171 (Isorhapontigenin)

3D PDB for HMDB0303171 (Isorhapontigenin)

SMILES for HMDB0303171 (Isorhapontigenin)

INCHI for HMDB0303171 (Isorhapontigenin)

Structure for HMDB0303171 (Isorhapontigenin)

3D Structure for HMDB0303171 (Isorhapontigenin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra