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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 04:45:42 UTC

Update Date

2021-09-24 04:45:43 UTC

HMDB ID

HMDB0303804

Secondary Accession Numbers

None

Metabolite Identification

Common Name

7-Epijasmonic acid

Description

7-epijasmonic acid, also known as (+)-epijasmonate, 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-epijasmonic acid is considered to be an octadecanoid lipid molecule. 7-epijasmonic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). 7-epijasmonic acid can be found in a number of food items such as broad bean, flaxseed, corn, and eggplant, which makes 7-epijasmonic acid a potential biomarker for the consumption of these food products.

Structure

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

HMDB0303804
     RDKit          3D
7-Epijasmonic acid
 33 33  0  0  0  0  0  0  0  0999 V2000
    4.7112    0.1584   -0.8651 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5245   -0.7378   -0.4403 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8073    0.0145    0.5821 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5654    0.3874    0.4968 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7205    0.0818   -0.6775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4363   -0.7345   -0.1659 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3949   -1.1363   -1.2018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2986   -1.1954   -2.4149 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6489   -1.5041   -0.4671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4267   -1.0682    0.9645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3092   -0.0224    0.8175 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9950    1.1934    0.1806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8454    1.8785    1.1682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9071    1.4322    2.3411 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5583    3.0029    0.7744 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5965   -0.4656   -1.1129 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4283    0.8107   -1.7054 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0102    0.8075   -0.0096 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0425   -1.6318    0.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9930   -1.0445   -1.3280 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3574    0.2839    1.4873 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0895    0.9680    1.3380 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3604    1.0307   -1.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1919   -0.5078   -1.4667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0429   -1.6371    0.3146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6808   -2.6195   -0.4575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5444   -1.0485   -0.9176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3203   -0.6770    1.4427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9911   -1.9077    1.5738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8461    0.2267    1.7680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6540    0.8698   -0.6511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2491    1.8790   -0.2581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2496    2.9128    0.0300 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  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 11  6  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  1
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  1
 12 31  1  0
 12 32  1  0
 15 33  1  0
M  END


  Mrv0541 02241221532D          

 15 15  0  0  1  0            999 V2000
    4.3737    1.6491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5891    1.3942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9760    1.9462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1913    1.6913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0198    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1296   -1.5764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6145   -2.2438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3091   -1.6626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0303804

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H18O3/c1-2-3-4-5-10-9(8-12(14)15)6-7-11(10)13/h3-4,9-10H,2,5-8H2,1H3,(H,14,15)/b4-3-/t9-,10+/m1/s1

> <INCHI_KEY>
ZNJFBWYDHIGLCU-QKMQQOOLSA-N

> <FORMULA>
C12H18O3

> <MOLECULAR_WEIGHT>
210.2695

> <EXACT_MASS>
210.125594442

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
23.253901334556318

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(1R,2S)-3-oxo-2-[(2Z)-pent-2-en-1-yl]cyclopentyl]acetic acid

> <ALOGPS_LOGP>
2.36

> <JCHEM_LOGP>
2.4143108776666664

> <ALOGPS_LOGS>
-2.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.714081549780867

> <JCHEM_PKA_STRONGEST_BASIC>
-7.4223839862661904

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
58.55650000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.20e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+)-7-iso-jasmonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0303804
     RDKit          3D
7-Epijasmonic acid
 33 33  0  0  0  0  0  0  0  0999 V2000
    4.7112    0.1584   -0.8651 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5245   -0.7378   -0.4403 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8073    0.0145    0.5821 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5654    0.3874    0.4968 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7205    0.0818   -0.6775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4363   -0.7345   -0.1659 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3949   -1.1363   -1.2018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2986   -1.1954   -2.4149 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6489   -1.5041   -0.4671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4267   -1.0682    0.9645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3092   -0.0224    0.8175 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9950    1.1934    0.1806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8454    1.8785    1.1682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9071    1.4322    2.3411 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5583    3.0029    0.7744 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5965   -0.4656   -1.1129 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4283    0.8107   -1.7054 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0102    0.8075   -0.0096 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0425   -1.6318    0.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9930   -1.0445   -1.3280 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3574    0.2839    1.4873 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0895    0.9680    1.3380 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3604    1.0307   -1.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1919   -0.5078   -1.4667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0429   -1.6371    0.3146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6808   -2.6195   -0.4575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5444   -1.0485   -0.9176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3203   -0.6770    1.4427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9911   -1.9077    1.5738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8461    0.2267    1.7680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6540    0.8698   -0.6511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2491    1.8790   -0.2581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2496    2.9128    0.0300 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  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 11  6  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  1
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  1
 12 31  1  0
 12 32  1  0
 15 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  C   UNK     0       8.164   3.078   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.700   2.603   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.555   3.633   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.090   3.157   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.770   1.651   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.735  -1.536   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.109  -2.943   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.014  -4.188   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.577  -3.104   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.060   3.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   14                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    7   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    6   15                                                  
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0303804
HETATM    1  C1  UNL     1       4.711   0.158  -0.865  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.524  -0.738  -0.440  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.807   0.015   0.582  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.565   0.387   0.497  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.721   0.082  -0.677  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.436  -0.734  -0.166  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.395  -1.136  -1.202  1.00  0.00           C  
HETATM    8  O1  UNL     1      -1.299  -1.195  -2.415  1.00  0.00           O  
HETATM    9  C8  UNL     1      -2.649  -1.504  -0.467  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.427  -1.068   0.965  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.309  -0.022   0.818  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.995   1.193   0.181  1.00  0.00           C  
HETATM   13  C12 UNL     1      -2.845   1.879   1.168  1.00  0.00           C  
HETATM   14  O2  UNL     1      -2.907   1.432   2.341  1.00  0.00           O  
HETATM   15  O3  UNL     1      -3.558   3.003   0.774  1.00  0.00           O  
HETATM   16  H1  UNL     1       5.596  -0.466  -1.113  1.00  0.00           H  
HETATM   17  H2  UNL     1       4.428   0.811  -1.705  1.00  0.00           H  
HETATM   18  H3  UNL     1       5.010   0.808  -0.010  1.00  0.00           H  
HETATM   19  H4  UNL     1       4.043  -1.632   0.033  1.00  0.00           H  
HETATM   20  H5  UNL     1       2.993  -1.045  -1.328  1.00  0.00           H  
HETATM   21  H6  UNL     1       3.357   0.284   1.487  1.00  0.00           H  
HETATM   22  H7  UNL     1       1.090   0.968   1.338  1.00  0.00           H  
HETATM   23  H8  UNL     1       0.360   1.031  -1.173  1.00  0.00           H  
HETATM   24  H9  UNL     1       1.192  -0.508  -1.467  1.00  0.00           H  
HETATM   25  H10 UNL     1      -0.043  -1.637   0.315  1.00  0.00           H  
HETATM   26  H11 UNL     1      -2.681  -2.619  -0.457  1.00  0.00           H  
HETATM   27  H12 UNL     1      -3.544  -1.049  -0.918  1.00  0.00           H  
HETATM   28  H13 UNL     1      -3.320  -0.677   1.443  1.00  0.00           H  
HETATM   29  H14 UNL     1      -1.991  -1.908   1.574  1.00  0.00           H  
HETATM   30  H15 UNL     1      -0.846   0.227   1.768  1.00  0.00           H  
HETATM   31  H16 UNL     1      -2.654   0.870  -0.651  1.00  0.00           H  
HETATM   32  H17 UNL     1      -1.249   1.879  -0.258  1.00  0.00           H  
HETATM   33  H18 UNL     1      -4.250   2.913   0.030  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3   19   20
CONECT    3    4    4   21
CONECT    4    5   22
CONECT    5    6   23   24
CONECT    6    7   11   25
CONECT    7    8    8    9
CONECT    9   10   26   27
CONECT   10   11   28   29
CONECT   11   12   30
CONECT   12   13   31   32
CONECT   13   14   14   15
CONECT   15   33
END

HMDB0303804
     RDKit          3D
7-Epijasmonic acid
 33 33  0  0  0  0  0  0  0  0999 V2000
    4.7112    0.1584   -0.8651 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5245   -0.7378   -0.4403 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8073    0.0145    0.5821 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5654    0.3874    0.4968 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7205    0.0818   -0.6775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4363   -0.7345   -0.1659 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3949   -1.1363   -1.2018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2986   -1.1954   -2.4149 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6489   -1.5041   -0.4671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4267   -1.0682    0.9645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3092   -0.0224    0.8175 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9950    1.1934    0.1806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8454    1.8785    1.1682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9071    1.4322    2.3411 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5583    3.0029    0.7744 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5965   -0.4656   -1.1129 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4283    0.8107   -1.7054 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0102    0.8075   -0.0096 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0425   -1.6318    0.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9930   -1.0445   -1.3280 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3574    0.2839    1.4873 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0895    0.9680    1.3380 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3604    1.0307   -1.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1919   -0.5078   -1.4667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0429   -1.6371    0.3146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6808   -2.6195   -0.4575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5444   -1.0485   -0.9176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3203   -0.6770    1.4427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9911   -1.9077    1.5738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8461    0.2267    1.7680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6540    0.8698   -0.6511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2491    1.8790   -0.2581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2496    2.9128    0.0300 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  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 11  6  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  1
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  1
 12 31  1  0
 12 32  1  0
 15 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+)-Epijasmonic acid	ChEBI
2-[(1R,2S)-3-oxo-2-[(Z)-Pent-2-enyl]cyclopentyl]acetic acid	ChEBI
(+)-Epijasmonate	Generator
2-[(1R,2S)-3-oxo-2-[(Z)-Pent-2-enyl]cyclopentyl]acetate	Generator
(+)-7-Isojasmonate	Generator
7-Epijasmonate	Generator

Chemical Formula

C₁₂H₁₈O₃

Average Molecular Weight

210.2695

Monoisotopic Molecular Weight

210.125594442

IUPAC Name

2-[(1R,2S)-3-oxo-2-[(2Z)-pent-2-en-1-yl]cyclopentyl]acetic acid

Traditional Name

(+)-7-iso-jasmonic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C12H18O3/c1-2-3-4-5-10-9(8-12(14)15)6-7-11(10)13/h3-4,9-10H,2,5-8H2,1H3,(H,14,15)/b4-3-/t9-,10+/m1/s1

InChI Key

ZNJFBWYDHIGLCU-QKMQQOOLSA-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
Cyclic ketone
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

oxo carboxylic acid (CHEBI:18435 )
oxylipin (CHEBI:18435 )
Jasmonic acids (C16317 )
Jasmonic acids (LMFA02020003 )

Ontology

Not Available

Eggplant (FooDB: FOOD00174)

Cereal and cereal product

Cereal

Corn (FooDB: FOOD00205)
Common wheat (FooDB: FOOD00187)

Herb and spice

Oilseed crop

Flaxseed (FooDB: FOOD00101)

Pulse

Bean

Broad bean (FooDB: FOOD00197)

Process

Not Available

Role

Not Available

Physical Properties

State

Liquid

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	2.36	ALOGPS
logP	2.41	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	4.71	ChemAxon
pKa (Strongest Basic)	-7.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	58.56 m³·mol⁻¹	ChemAxon
Polarizability	23.25 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]+	149.922	32859911
AllCCS	[M+H-H2O]+	146.092	32859911
AllCCS	[M+Na]+	154.507	32859911
AllCCS	[M+NH4]+	153.482	32859911
AllCCS	[M-H]-	152.679	32859911
AllCCS	[M+Na-2H]-	153.406	32859911
AllCCS	[M+HCOO]-	154.306	32859911
DeepCCS	[M+H]+	154.186	30932474
DeepCCS	[M-H]-	151.828	30932474
DeepCCS	[M-2H]-	184.714	30932474
DeepCCS	[M+Na]+	160.28	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
7-Epijasmonic acid,2TMS,isomer #1	CC/C=C\CC1=C(O[Si](C)(C)C)CC[C@@H]1CC(=O)O[Si](C)(C)C	1875.3	Semi standard non polar	33892256
7-Epijasmonic acid,2TMS,isomer #1	CC/C=C\CC1=C(O[Si](C)(C)C)CC[C@@H]1CC(=O)O[Si](C)(C)C	1903.8	Standard non polar	33892256
7-Epijasmonic acid,2TMS,isomer #1	CC/C=C\CC1=C(O[Si](C)(C)C)CC[C@@H]1CC(=O)O[Si](C)(C)C	2077.8	Standard polar	33892256
7-Epijasmonic acid,2TMS,isomer #2	CC/C=C\C[C@@H]1C(O[Si](C)(C)C)=CC[C@@H]1CC(=O)O[Si](C)(C)C	1864.3	Semi standard non polar	33892256
7-Epijasmonic acid,2TMS,isomer #2	CC/C=C\C[C@@H]1C(O[Si](C)(C)C)=CC[C@@H]1CC(=O)O[Si](C)(C)C	1907.1	Standard non polar	33892256
7-Epijasmonic acid,2TMS,isomer #2	CC/C=C\C[C@@H]1C(O[Si](C)(C)C)=CC[C@@H]1CC(=O)O[Si](C)(C)C	2121.1	Standard polar	33892256
7-Epijasmonic acid,2TBDMS,isomer #1	CC/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	2337.2	Semi standard non polar	33892256
7-Epijasmonic acid,2TBDMS,isomer #1	CC/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	2288.6	Standard non polar	33892256
7-Epijasmonic acid,2TBDMS,isomer #1	CC/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	2315.2	Standard polar	33892256
7-Epijasmonic acid,2TBDMS,isomer #2	CC/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	2310.3	Semi standard non polar	33892256
7-Epijasmonic acid,2TBDMS,isomer #2	CC/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	2182.7	Standard non polar	33892256
7-Epijasmonic acid,2TBDMS,isomer #2	CC/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	2332.1	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-Epijasmonic acid 10V, Positive-QTOF	splash10-0006-0920000000-3e2ea863902c1443a94a	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Epijasmonic acid 20V, Positive-QTOF	splash10-0159-9800000000-cae0998084e31d20ae28	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Epijasmonic acid 40V, Positive-QTOF	splash10-0fa6-9100000000-16ffc051b7554d43e070	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Epijasmonic acid 10V, Negative-QTOF	splash10-0aor-0890000000-0b084a22341872dc4af0	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Epijasmonic acid 20V, Negative-QTOF	splash10-0aou-1940000000-1d0644783ca38085565d	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Epijasmonic acid 40V, Negative-QTOF	splash10-0a4m-9500000000-8162c16141e7817b5f64	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Epijasmonic acid 10V, Positive-QTOF	splash10-0gyp-2910000000-a69f966566f2bc59fb69	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Epijasmonic acid 20V, Positive-QTOF	splash10-001j-5900000000-2ec8ca38efed6833e272	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Epijasmonic acid 40V, Positive-QTOF	splash10-005c-9000000000-95226024b29c669c7cfd	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Epijasmonic acid 10V, Negative-QTOF	splash10-0a4i-9000000000-ec3571c239d0c5c37921	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Epijasmonic acid 20V, Negative-QTOF	splash10-0a4i-9000000000-396cf428ae175e04137f	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Epijasmonic acid 40V, Negative-QTOF	splash10-0006-9000000000-0ee0c89f8c924a9c618f	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

FDB021719

KNApSAcK ID

Not Available

Chemspider ID

5584839

KEGG Compound ID

C16317

BioCyc ID

CPD-731

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

18435

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-Epijasmonic acid (HMDB0303804)

MOL for HMDB0303804 (7-Epijasmonic acid)

3D MOL for HMDB0303804 (7-Epijasmonic acid)

3D SDF for HMDB0303804 (7-Epijasmonic acid)

3D-SDF for HMDB0303804 (7-Epijasmonic acid)

PDB for HMDB0303804 (7-Epijasmonic acid)

3D PDB for HMDB0303804 (7-Epijasmonic acid)

SMILES for HMDB0303804 (7-Epijasmonic acid)

INCHI for HMDB0303804 (7-Epijasmonic acid)

Structure for HMDB0303804 (7-Epijasmonic acid)

3D Structure for HMDB0303804 (7-Epijasmonic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra