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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 04:20:45 UTC

Update Date

2021-09-24 04:20:45 UTC

HMDB ID

HMDB0303749

Secondary Accession Numbers

None

Metabolite Identification

Common Name

7-Epi-12-hydroxyjasmonic acid

Description

7-epi-12-hydroxyjasmonic acid, also known as (+)-12-hydroxy-7-isojasmonate, is a member of the class of compounds known as jasmonic acids. Jasmonic acids are lipids containing or derived from a jasmonic acid, with a structure characterized by the presence of an alkene chain linked to a 2-(3-oxocyclopentyl)acetic acid moiety. Thus, 7-epi-12-hydroxyjasmonic acid is considered to be an octadecanoid lipid molecule. 7-epi-12-hydroxyjasmonic acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa). 7-epi-12-hydroxyjasmonic acid can be synthesized from (+)-7-isojasmonic acid. 7-epi-12-hydroxyjasmonic acid can also be synthesized into N-[(+)-12-hydroxy-7-isojasmonyl]-L-isoleucine and methyl tuberonate. 7-epi-12-hydroxyjasmonic acid can be found in potato, which makes 7-epi-12-hydroxyjasmonic acid a potential biomarker for the consumption of this food product.

Structure

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

HMDB0303749
     RDKit          3D
7-Epi-12-hydroxyjasmonic acid
 34 34  0  0  0  0  0  0  0  0999 V2000
    4.2845   -1.1403    1.2831 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8306    0.0106    1.2589 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7072    1.0792    1.2607 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3527    0.3418    1.2265 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9555    0.3160   -0.1943 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2084   -1.1090   -0.7134 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9077   -1.5572   -1.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0632   -0.3679   -1.4653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9747   -0.3059   -2.0993 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6844    0.7757   -0.6788 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3862    1.3263    0.1722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9454    0.4637    1.2071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1767    0.0446    1.3536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2422    0.4233    0.4111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8597   -0.8318   -0.2426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8480   -0.3159   -1.1073 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4291    2.0400    1.1241 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2538    1.2684    1.7792 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9213   -0.5413    1.8056 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8089    0.8967   -0.7240 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4121   -1.8179    0.1082 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9948   -1.1768   -1.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0992   -2.0121   -2.3577 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3945   -2.3324   -0.7569 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8647    1.5317   -1.5201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0605    2.2573    0.7339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1929    1.7238   -0.4752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2541    0.1112    1.9960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4488   -0.6240    2.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1278    0.8752    0.9529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9123    1.0352   -0.4111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1134   -1.4032   -0.7882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3559   -1.4249    0.5352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2739    0.4397   -0.6384 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 10  5  1  0
  3 17  1  0
  4 18  1  0
  4 19  1  0
  5 20  1  6
  6 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
 10 25  1  6
 11 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
 16 34  1  0
M  END


  Mrv0541 02241220432D          

 16 16  0  0  1  0            999 V2000
    2.2696   -0.9636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7846   -0.2961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9641   -0.3824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1202    0.4575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6353    1.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8902    1.9096    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2228    2.3946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2228    3.2195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5553    1.9096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8103    1.1249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6748    2.1645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8463    2.9715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6309    3.2264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2441    2.6744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0725    1.8675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6856    1.3154    0.0000 O   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
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
  6 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0303749

> <DATABASE_NAME>
hmdb

> <SMILES>
OCC\C=C/C[C@H]1[C@@H](CC(O)=O)CCC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H18O4/c13-7-3-1-2-4-10-9(8-12(15)16)5-6-11(10)14/h1-2,9-10,13H,3-8H2,(H,15,16)/b2-1-/t9-,10+/m1/s1

> <INCHI_KEY>
RZGFUGXQKMEMOO-SZXTZRQCSA-N

> <FORMULA>
C12H18O4

> <MOLECULAR_WEIGHT>
226.2689

> <EXACT_MASS>
226.120509064

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
23.897110097780953

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(1R,2S)-2-[(2Z)-5-hydroxypent-2-en-1-yl]-3-oxocyclopentyl]acetic acid

> <ALOGPS_LOGP>
0.87

> <JCHEM_LOGP>
0.9776322610000004

> <ALOGPS_LOGS>
-2.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.791594249561193

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.462628719201375

> <JCHEM_PKA_STRONGEST_BASIC>
-2.0150707610109873

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
60.485200000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.28e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tuberonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0303749
     RDKit          3D
7-Epi-12-hydroxyjasmonic acid
 34 34  0  0  0  0  0  0  0  0999 V2000
    4.2845   -1.1403    1.2831 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8306    0.0106    1.2589 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7072    1.0792    1.2607 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3527    0.3418    1.2265 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9555    0.3160   -0.1943 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2084   -1.1090   -0.7134 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9077   -1.5572   -1.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0632   -0.3679   -1.4653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9747   -0.3059   -2.0993 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6844    0.7757   -0.6788 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3862    1.3263    0.1722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9454    0.4637    1.2071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1767    0.0446    1.3536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2422    0.4233    0.4111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8597   -0.8318   -0.2426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8480   -0.3159   -1.1073 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4291    2.0400    1.1241 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2538    1.2684    1.7792 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9213   -0.5413    1.8056 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8089    0.8967   -0.7240 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4121   -1.8179    0.1082 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9948   -1.1768   -1.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0992   -2.0121   -2.3577 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3945   -2.3324   -0.7569 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8647    1.5317   -1.5201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0605    2.2573    0.7339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1929    1.7238   -0.4752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2541    0.1112    1.9960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4488   -0.6240    2.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1278    0.8752    0.9529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9123    1.0352   -0.4111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1134   -1.4032   -0.7882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3559   -1.4249    0.5352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2739    0.4397   -0.6384 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 10  5  1  0
  3 17  1  0
  4 18  1  0
  4 19  1  0
  5 20  1  6
  6 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
 10 25  1  6
 11 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
 16 34  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       4.237  -1.799   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.331  -0.553   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.800  -0.714   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       3.958   0.854   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.053   2.100   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.528   3.565   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.283   4.470   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.283   6.010   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.037   3.565   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.513   2.100   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.993   4.040   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.313   5.547   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.778   6.023   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.922   4.992   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.602   3.486   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.746   2.455   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9    5                                                       
CONECT   11    6   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0303749
HETATM    1  O1  UNL     1       4.284  -1.140   1.283  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.831   0.011   1.259  1.00  0.00           C  
HETATM    3  O2  UNL     1       4.707   1.079   1.261  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.353   0.342   1.226  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.955   0.316  -0.194  1.00  0.00           C  
HETATM    6  C4  UNL     1       2.208  -1.109  -0.713  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.908  -1.557  -1.343  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.063  -0.368  -1.465  1.00  0.00           C  
HETATM    9  O3  UNL     1      -0.975  -0.306  -2.099  1.00  0.00           O  
HETATM   10  C7  UNL     1       0.684   0.776  -0.679  1.00  0.00           C  
HETATM   11  C8  UNL     1      -0.386   1.326   0.172  1.00  0.00           C  
HETATM   12  C9  UNL     1      -0.945   0.464   1.207  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.177   0.045   1.354  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.242   0.423   0.411  1.00  0.00           C  
HETATM   15  C12 UNL     1      -3.860  -0.832  -0.243  1.00  0.00           C  
HETATM   16  O4  UNL     1      -4.848  -0.316  -1.107  1.00  0.00           O  
HETATM   17  H1  UNL     1       4.429   2.040   1.124  1.00  0.00           H  
HETATM   18  H2  UNL     1       2.254   1.268   1.779  1.00  0.00           H  
HETATM   19  H3  UNL     1       1.921  -0.541   1.806  1.00  0.00           H  
HETATM   20  H4  UNL     1       2.809   0.897  -0.724  1.00  0.00           H  
HETATM   21  H5  UNL     1       2.412  -1.818   0.108  1.00  0.00           H  
HETATM   22  H6  UNL     1       2.995  -1.177  -1.456  1.00  0.00           H  
HETATM   23  H7  UNL     1       1.099  -2.012  -2.358  1.00  0.00           H  
HETATM   24  H8  UNL     1       0.395  -2.332  -0.757  1.00  0.00           H  
HETATM   25  H9  UNL     1       0.865   1.532  -1.520  1.00  0.00           H  
HETATM   26  H10 UNL     1      -0.060   2.257   0.734  1.00  0.00           H  
HETATM   27  H11 UNL     1      -1.193   1.724  -0.475  1.00  0.00           H  
HETATM   28  H12 UNL     1      -0.254   0.111   1.996  1.00  0.00           H  
HETATM   29  H13 UNL     1      -2.449  -0.624   2.217  1.00  0.00           H  
HETATM   30  H14 UNL     1      -4.128   0.875   0.953  1.00  0.00           H  
HETATM   31  H15 UNL     1      -2.912   1.035  -0.411  1.00  0.00           H  
HETATM   32  H16 UNL     1      -3.113  -1.403  -0.788  1.00  0.00           H  
HETATM   33  H17 UNL     1      -4.356  -1.425   0.535  1.00  0.00           H  
HETATM   34  H18 UNL     1      -5.274   0.440  -0.638  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   17
CONECT    4    5   18   19
CONECT    5    6   10   20
CONECT    6    7   21   22
CONECT    7    8   23   24
CONECT    8    9    9   10
CONECT   10   11   25
CONECT   11   12   26   27
CONECT   12   13   13   28
CONECT   13   14   29
CONECT   14   15   30   31
CONECT   15   16   32   33
CONECT   16   34
END

HMDB0303749
     RDKit          3D
7-Epi-12-hydroxyjasmonic acid
 34 34  0  0  0  0  0  0  0  0999 V2000
    4.2845   -1.1403    1.2831 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8306    0.0106    1.2589 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7072    1.0792    1.2607 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3527    0.3418    1.2265 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9555    0.3160   -0.1943 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2084   -1.1090   -0.7134 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9077   -1.5572   -1.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0632   -0.3679   -1.4653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9747   -0.3059   -2.0993 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6844    0.7757   -0.6788 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3862    1.3263    0.1722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9454    0.4637    1.2071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1767    0.0446    1.3536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2422    0.4233    0.4111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8597   -0.8318   -0.2426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8480   -0.3159   -1.1073 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4291    2.0400    1.1241 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2538    1.2684    1.7792 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9213   -0.5413    1.8056 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8089    0.8967   -0.7240 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4121   -1.8179    0.1082 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9948   -1.1768   -1.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0992   -2.0121   -2.3577 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3945   -2.3324   -0.7569 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8647    1.5317   -1.5201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0605    2.2573    0.7339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1929    1.7238   -0.4752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2541    0.1112    1.9960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4488   -0.6240    2.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1278    0.8752    0.9529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9123    1.0352   -0.4111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1134   -1.4032   -0.7882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3559   -1.4249    0.5352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2739    0.4397   -0.6384 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 10  5  1  0
  3 17  1  0
  4 18  1  0
  4 19  1  0
  5 20  1  6
  6 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
 10 25  1  6
 11 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
 16 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+)-12-Hydroxy-7-isojasmonic acid	ChEBI
(1R,2S)-3-oxo-2-(5'-Hydroxy-2'z-pentenyl)-cyclopentaneacetic acid	ChEBI
12-Hydroxy-epi-jasmonic acid	ChEBI
(+)-12-Hydroxy-7-isojasmonate	Generator
(1R,2S)-3-oxo-2-(5'-Hydroxy-2'z-pentenyl)-cyclopentaneacetate	Generator
12-Hydroxy-epi-jasmonate	Generator
Tuberonate	Generator
7-Epi-12-hydroxyjasmonate	Generator

Chemical Formula

C₁₂H₁₈O₄

Average Molecular Weight

226.2689

Monoisotopic Molecular Weight

226.120509064

IUPAC Name

2-[(1R,2S)-2-[(2Z)-5-hydroxypent-2-en-1-yl]-3-oxocyclopentyl]acetic acid

Traditional Name

tuberonic acid

CAS Registry Number

Not Available

SMILES

OCC\C=C/C[C@H]1[C@@H](CC(O)=O)CCC1=O

InChI Identifier

InChI=1S/C12H18O4/c13-7-3-1-2-4-10-9(8-12(15)16)5-6-11(10)14/h1-2,9-10,13H,3-8H2,(H,15,16)/b2-1-/t9-,10+/m1/s1

InChI Key

RZGFUGXQKMEMOO-SZXTZRQCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as jasmonic acids. These are lipids containing or derived from a jasmonic acid, with a structure characterized by the presence of an alkene chain linked to a 2-(3-oxocyclopentyl)acetic acid moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Lineolic acids and derivatives

Direct Parent

Jasmonic acids

Alternative Parents

Substituents

Jasmonic acid
Fatty alcohol
Cyclic ketone
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Jasmonic acids (LMFA02020007 )

Ontology

Not Available

Exogenous (HMDB: HMDB0303749)

Food

Vegetable

Tuber

Potato (FooDB: FOOD00175)

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	0.87	ALOGPS
logP	0.98	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	4.46	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	60.49 m³·mol⁻¹	ChemAxon
Polarizability	23.9 Å³	ChemAxon
Number of Rings	1	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]+	151.886	32859911
AllCCS	[M+H-H2O]+	148.254	32859911
AllCCS	[M+Na]+	156.229	32859911
AllCCS	[M+NH4]+	155.259	32859911
AllCCS	[M-H]-	154.954	32859911
AllCCS	[M+Na-2H]-	155.522	32859911
AllCCS	[M+HCOO]-	156.253	32859911
DeepCCS	[M+H]+	156.559	30932474
DeepCCS	[M-H]-	154.201	30932474
DeepCCS	[M-2H]-	187.087	30932474
DeepCCS	[M+Na]+	162.652	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
7-Epi-12-hydroxyjasmonic acid,3TMS,isomer #1	C[Si](C)(C)OCC/C=C\CC1=C(O[Si](C)(C)C)CC[C@@H]1CC(=O)O[Si](C)(C)C	2116.7	Semi standard non polar	33892256
7-Epi-12-hydroxyjasmonic acid,3TMS,isomer #1	C[Si](C)(C)OCC/C=C\CC1=C(O[Si](C)(C)C)CC[C@@H]1CC(=O)O[Si](C)(C)C	2191.6	Standard non polar	33892256
7-Epi-12-hydroxyjasmonic acid,3TMS,isomer #1	C[Si](C)(C)OCC/C=C\CC1=C(O[Si](C)(C)C)CC[C@@H]1CC(=O)O[Si](C)(C)C	2213.9	Standard polar	33892256
7-Epi-12-hydroxyjasmonic acid,3TMS,isomer #2	C[Si](C)(C)OCC/C=C\C[C@@H]1C(O[Si](C)(C)C)=CC[C@@H]1CC(=O)O[Si](C)(C)C	2104.1	Semi standard non polar	33892256
7-Epi-12-hydroxyjasmonic acid,3TMS,isomer #2	C[Si](C)(C)OCC/C=C\C[C@@H]1C(O[Si](C)(C)C)=CC[C@@H]1CC(=O)O[Si](C)(C)C	2190.4	Standard non polar	33892256
7-Epi-12-hydroxyjasmonic acid,3TMS,isomer #2	C[Si](C)(C)OCC/C=C\C[C@@H]1C(O[Si](C)(C)C)=CC[C@@H]1CC(=O)O[Si](C)(C)C	2262.1	Standard polar	33892256
7-Epi-12-hydroxyjasmonic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC/C=C\CC1=C(O[Si](C)(C)C(C)(C)C)CC[C@@H]1CC(=O)O[Si](C)(C)C(C)(C)C	2832.8	Semi standard non polar	33892256
7-Epi-12-hydroxyjasmonic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC/C=C\CC1=C(O[Si](C)(C)C(C)(C)C)CC[C@@H]1CC(=O)O[Si](C)(C)C(C)(C)C	2739.0	Standard non polar	33892256
7-Epi-12-hydroxyjasmonic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC/C=C\CC1=C(O[Si](C)(C)C(C)(C)C)CC[C@@H]1CC(=O)O[Si](C)(C)C(C)(C)C	2538.2	Standard polar	33892256
7-Epi-12-hydroxyjasmonic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC/C=C\C[C@@H]1C(O[Si](C)(C)C(C)(C)C)=CC[C@@H]1CC(=O)O[Si](C)(C)C(C)(C)C	2797.6	Semi standard non polar	33892256
7-Epi-12-hydroxyjasmonic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC/C=C\C[C@@H]1C(O[Si](C)(C)C(C)(C)C)=CC[C@@H]1CC(=O)O[Si](C)(C)C(C)(C)C	2590.8	Standard non polar	33892256
7-Epi-12-hydroxyjasmonic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC/C=C\C[C@@H]1C(O[Si](C)(C)C(C)(C)C)=CC[C@@H]1CC(=O)O[Si](C)(C)C(C)(C)C	2537.4	Standard polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Epi-12-hydroxyjasmonic acid 10V, Positive-QTOF	splash10-0a4i-0690000000-f359119ef6a4806dedf1	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Epi-12-hydroxyjasmonic acid 20V, Positive-QTOF	splash10-0ced-5920000000-0f61d47d70826442d9ef	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Epi-12-hydroxyjasmonic acid 40V, Positive-QTOF	splash10-0f75-9300000000-765d8f3d969573a2dc28	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Epi-12-hydroxyjasmonic acid 10V, Negative-QTOF	splash10-004i-0590000000-bc05ff34bb7b310cf674	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Epi-12-hydroxyjasmonic acid 20V, Negative-QTOF	splash10-056r-1970000000-1f6525523f3a4720baa0	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Epi-12-hydroxyjasmonic acid 40V, Negative-QTOF	splash10-0a4l-9700000000-ad780e290058a24e1a2b	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Epi-12-hydroxyjasmonic acid 10V, Positive-QTOF	splash10-05te-1920000000-f7c40d9495987d8faec7	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Epi-12-hydroxyjasmonic acid 20V, Positive-QTOF	splash10-0002-5900000000-bc9f3a29fb5b4cd9f015	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Epi-12-hydroxyjasmonic acid 40V, Positive-QTOF	splash10-0aou-9300000000-0278a248d334c36f5d39	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Epi-12-hydroxyjasmonic acid 10V, Negative-QTOF	splash10-0a4i-9020000000-8c2f9eff8d1ef349c066	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Epi-12-hydroxyjasmonic acid 20V, Negative-QTOF	splash10-0a4i-9110000000-5ec466540a66e665045d	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Epi-12-hydroxyjasmonic acid 40V, Negative-QTOF	splash10-0006-9200000000-353b1213d492f4511673	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

FDB020508

KNApSAcK ID

C00000221

Chemspider ID

4947920

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6443968

PDB ID

Not Available

ChEBI ID

133220

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 7-Epi-12-hydroxyjasmonic acid (HMDB0303749)

MOL for HMDB0303749 (7-Epi-12-hydroxyjasmonic acid)

3D MOL for HMDB0303749 (7-Epi-12-hydroxyjasmonic acid)

3D SDF for HMDB0303749 (7-Epi-12-hydroxyjasmonic acid)

3D-SDF for HMDB0303749 (7-Epi-12-hydroxyjasmonic acid)

PDB for HMDB0303749 (7-Epi-12-hydroxyjasmonic acid)

3D PDB for HMDB0303749 (7-Epi-12-hydroxyjasmonic acid)

SMILES for HMDB0303749 (7-Epi-12-hydroxyjasmonic acid)

INCHI for HMDB0303749 (7-Epi-12-hydroxyjasmonic acid)

Structure for HMDB0303749 (7-Epi-12-hydroxyjasmonic acid)

3D Structure for HMDB0303749 (7-Epi-12-hydroxyjasmonic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra