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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:51:53 UTC

Update Date

2023-02-21 17:22:40 UTC

HMDB ID

HMDB0032797

Secondary Accession Numbers

HMDB32797

Metabolite Identification

Common Name

Jasmonic acid

Description

Jasmonic acid, also known as jasmonate, 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. Based on a literature review a significant number of articles have been published on Jasmonic acid.

Structure

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

HMDB0032797
     RDKit          3D
Jasmonic acid
 33 33  0  0  0  0  0  0  0  0999 V2000
    4.3761    0.8764   -0.1918 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0034    0.5926   -0.7736 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5804   -0.7849   -0.6240 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5138   -1.1773    0.0235 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6135   -0.2055    0.6853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7536   -0.4120    0.0048 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1661   -1.8227    0.2382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9901   -2.7724   -0.4955 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8386   -1.8336    1.5546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6137   -0.5562    1.5682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8243    0.3892    0.7028 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7476    0.9265   -0.3803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0250    1.7942   -1.3442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7144    2.9416   -0.9775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7147    1.3312   -2.6003 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3091    1.2131    0.8659 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7977    1.7294   -0.7615 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0469    0.0174   -0.3371 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3542    1.3976   -0.4863 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1620    0.7393   -1.8976 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1745   -1.6162   -1.0764 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2644   -2.2753    0.0852 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8882    0.8373    0.5799 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4118   -0.4863    1.7499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6312   -0.1455   -1.0424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0941   -1.8557    2.3829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4998   -2.7205    1.6660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7430   -0.1477    2.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6505   -0.7289    1.1634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4381    1.2340    1.2811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2390    0.1192   -0.9467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5556    1.5305    0.0829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2567    1.8712   -3.3052 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  6
  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

  Mrv1652309272007362D          

 15 15  0  0  0  0            999 V2000
 9999.3011 9999.3772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3011 9998.5522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5868 9998.1409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.0154 9998.1409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.561010000.9619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.275110000.5497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.099510000.5497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.814610000.9619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.529810000.5497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.193710001.8790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.175310001.0441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.507910000.5591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.7628 9999.7745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5878 9999.7745    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.842710000.5591    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 11 12  1  0  0  0  0
 11 15  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14  1  1  1  0  0  0
 15  5  1  6  0  0  0
 11 10  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032797

> <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-HWKXXFMVSA-N

> <FORMULA>
C12H18O3

> <MOLECULAR_WEIGHT>
210.2695

> <EXACT_MASS>
210.125594442

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
22.928474980220432

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(1R,2R)-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>
jasmonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0032797
     RDKit          3D
Jasmonic acid
 33 33  0  0  0  0  0  0  0  0999 V2000
    4.3761    0.8764   -0.1918 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0034    0.5926   -0.7736 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5804   -0.7849   -0.6240 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5138   -1.1773    0.0235 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6135   -0.2055    0.6853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7536   -0.4120    0.0048 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1661   -1.8227    0.2382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9901   -2.7724   -0.4955 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8386   -1.8336    1.5546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6137   -0.5562    1.5682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8243    0.3892    0.7028 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7476    0.9265   -0.3803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0250    1.7942   -1.3442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7144    2.9416   -0.9775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7147    1.3312   -2.6003 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3091    1.2131    0.8659 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7977    1.7294   -0.7615 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0469    0.0174   -0.3371 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3542    1.3976   -0.4863 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1620    0.7393   -1.8976 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1745   -1.6162   -1.0764 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2644   -2.2753    0.0852 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8882    0.8373    0.5799 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4118   -0.4863    1.7499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6312   -0.1455   -1.0424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0941   -1.8557    2.3829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4998   -2.7205    1.6660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7430   -0.1477    2.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6505   -0.7289    1.1634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4381    1.2340    1.2811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2390    0.1192   -0.9467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5556    1.5305    0.0829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2567    1.8712   -3.3052 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  6
  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                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8665.3628665.504   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8665.3628663.964   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8664.0298663.196   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8666.6958663.196   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    8665.8478668.462   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8667.1808667.693   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8668.7198667.693   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8670.0548668.462   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8671.3898667.693   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    8663.2958670.174   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0    8663.2618668.616   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8662.0158667.710   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8662.4918666.246   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8664.0318666.246   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8664.5068667.710   0.000  0.00  0.00           C+0
CONECT    1    2   14                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    6   15                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10   11                                                            
CONECT   11   12   15   10                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15    1                                                  
CONECT   15   11   14    5                                                  
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0032797
HETATM    1  C1  UNL     1       4.376   0.876  -0.192  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.003   0.593  -0.774  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.580  -0.785  -0.624  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.514  -1.177   0.023  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.613  -0.206   0.685  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.754  -0.412   0.005  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.166  -1.823   0.238  1.00  0.00           C  
HETATM    8  O1  UNL     1      -0.990  -2.772  -0.495  1.00  0.00           O  
HETATM    9  C8  UNL     1      -1.839  -1.834   1.555  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.614  -0.556   1.568  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.824   0.389   0.703  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.748   0.927  -0.380  1.00  0.00           C  
HETATM   13  C12 UNL     1      -2.025   1.794  -1.344  1.00  0.00           C  
HETATM   14  O2  UNL     1      -1.714   2.942  -0.978  1.00  0.00           O  
HETATM   15  O3  UNL     1      -1.715   1.331  -2.600  1.00  0.00           O  
HETATM   16  H1  UNL     1       4.309   1.213   0.866  1.00  0.00           H  
HETATM   17  H2  UNL     1       4.798   1.729  -0.761  1.00  0.00           H  
HETATM   18  H3  UNL     1       5.047   0.017  -0.337  1.00  0.00           H  
HETATM   19  H4  UNL     1       2.354   1.398  -0.486  1.00  0.00           H  
HETATM   20  H5  UNL     1       3.162   0.739  -1.898  1.00  0.00           H  
HETATM   21  H6  UNL     1       3.174  -1.616  -1.076  1.00  0.00           H  
HETATM   22  H7  UNL     1       1.264  -2.275   0.085  1.00  0.00           H  
HETATM   23  H8  UNL     1       0.888   0.837   0.580  1.00  0.00           H  
HETATM   24  H9  UNL     1       0.412  -0.486   1.750  1.00  0.00           H  
HETATM   25  H10 UNL     1      -0.631  -0.145  -1.042  1.00  0.00           H  
HETATM   26  H11 UNL     1      -1.094  -1.856   2.383  1.00  0.00           H  
HETATM   27  H12 UNL     1      -2.500  -2.720   1.666  1.00  0.00           H  
HETATM   28  H13 UNL     1      -2.743  -0.148   2.606  1.00  0.00           H  
HETATM   29  H14 UNL     1      -3.650  -0.729   1.163  1.00  0.00           H  
HETATM   30  H15 UNL     1      -1.438   1.234   1.281  1.00  0.00           H  
HETATM   31  H16 UNL     1      -3.239   0.119  -0.947  1.00  0.00           H  
HETATM   32  H17 UNL     1      -3.556   1.531   0.083  1.00  0.00           H  
HETATM   33  H18 UNL     1      -1.257   1.871  -3.305  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

HMDB0032797
     RDKit          3D
Jasmonic acid
 33 33  0  0  0  0  0  0  0  0999 V2000
    4.3761    0.8764   -0.1918 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0034    0.5926   -0.7736 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5804   -0.7849   -0.6240 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5138   -1.1773    0.0235 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6135   -0.2055    0.6853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7536   -0.4120    0.0048 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1661   -1.8227    0.2382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9901   -2.7724   -0.4955 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8386   -1.8336    1.5546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6137   -0.5562    1.5682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8243    0.3892    0.7028 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7476    0.9265   -0.3803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0250    1.7942   -1.3442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7144    2.9416   -0.9775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7147    1.3312   -2.6003 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3091    1.2131    0.8659 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7977    1.7294   -0.7615 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0469    0.0174   -0.3371 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3542    1.3976   -0.4863 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1620    0.7393   -1.8976 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1745   -1.6162   -1.0764 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2644   -2.2753    0.0852 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8882    0.8373    0.5799 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4118   -0.4863    1.7499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6312   -0.1455   -1.0424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0941   -1.8557    2.3829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4998   -2.7205    1.6660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7430   -0.1477    2.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6505   -0.7289    1.1634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4381    1.2340    1.2811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2390    0.1192   -0.9467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5556    1.5305    0.0829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2567    1.8712   -3.3052 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  6
  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
(-)-Jasmonic acid	ChEBI
(1R,2R)-3-oxo-2-(2Z)-2-Penten-ylcyclopentanacetic acid	ChEBI
(1R,2R)-3-oxo-2-(Pent-2Z-enyl)-cyclopentaneacetic acid	ChEBI
2-{(1R,2R)-3-oxo-2-[(Z)-pent-2-enyl]cyclopentyl}acetate	ChEBI
Jasmonate	ChEBI
{(1R,2R)-3-oxo-2-[(Z)pent-2-enyl]cyclopent-2-enyl}acetic acid	Kegg
(-)-Jasmonate	Kegg
(1R,2R)-3-oxo-2-(2Z)-2-Penten-ylcyclopentanacetate	Generator
(1R,2R)-3-oxo-2-(Pent-2Z-enyl)-cyclopentaneacetate	Generator
2-{(1R,2R)-3-oxo-2-[(Z)-pent-2-enyl]cyclopentyl}acetic acid	Generator
{(1R,2R)-3-oxo-2-[(Z)pent-2-enyl]cyclopent-2-enyl}acetate	Generator
7-Epi-jasmonic acid	MeSH
(Z)-trans-3-Oxo-2-(2-pentenyl)-cyclopentaneacetic acid	PhytoBank
[1R-[1alpha,2beta(Z)]]-3-Oxo-2-(2-pentenyl)-cyclopentaneacetic acid	PhytoBank
[1R-[1α,2β(Z)]]-3-Oxo-2-(2-pentenyl)-cyclopentaneacetic acid	PhytoBank
(1R,2R)-3-Oxo-2-(2Z)-2-pentenyl-cyclopentaneacetic acid	PhytoBank
(1R,2R)-3-Oxo-2-(2Z)-2-penten-1-ylcyclopentaneacetic acid	PhytoBank
(1R,2R)-Jasmonic acid	PhytoBank
(3R,7R)(-)-Jasmonic acid	PhytoBank
JA	PhytoBank

Chemical Formula

C₁₂H₁₈O₃

Average Molecular Weight

210.2695

Monoisotopic Molecular Weight

210.125594442

IUPAC Name

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

Traditional Name

jasmonic acid

CAS Registry Number

6894-38-8

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-HWKXXFMVSA-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 monocarboxylic acid (CHEBI:18292 )
Jasmonic acids (C08491 )
Fatty acids (C08491 )
Jasmonic acids (LMFA02020001 )

Ontology

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	742.1 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.92 g/L	ALOGPS
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	22.93 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
DarkChem	[M+H]+	152.827	31661259
DarkChem	[M-H]-	146.595	31661259
DeepCCS	[M+H]+	154.594	30932474
DeepCCS	[M-H]-	152.23	30932474
DeepCCS	[M-2H]-	185.116	30932474
DeepCCS	[M+Na]+	160.682	30932474
AllCCS	[M+H]+	149.9	32859911
AllCCS	[M+H-H2O]+	146.1	32859911
AllCCS	[M+NH4]+	153.5	32859911
AllCCS	[M+Na]+	154.5	32859911
AllCCS	[M-H]-	152.7	32859911
AllCCS	[M+Na-2H]-	153.4	32859911
AllCCS	[M+HCOO]-	154.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Jasmonic acid	CC\C=C/C[C@@H]1[C@@H](CC(O)=O)CCC1=O	3026.1	Standard polar	33892256
Jasmonic acid	CC\C=C/C[C@@H]1[C@@H](CC(O)=O)CCC1=O	1680.6	Standard non polar	33892256
Jasmonic acid	CC\C=C/C[C@@H]1[C@@H](CC(O)=O)CCC1=O	1714.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Jasmonic acid,1TMS,isomer #1	CC/C=C\C[C@H]1C(=O)CC[C@@H]1CC(=O)O[Si](C)(C)C	1780.3	Semi standard non polar	33892256
Jasmonic acid,1TMS,isomer #2	CC/C=C\CC1=C(O[Si](C)(C)C)CC[C@@H]1CC(=O)O	1865.7	Semi standard non polar	33892256
Jasmonic acid,1TMS,isomer #3	CC/C=C\C[C@H]1C(O[Si](C)(C)C)=CC[C@@H]1CC(=O)O	1838.4	Semi standard non polar	33892256
Jasmonic 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
Jasmonic 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
Jasmonic 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
Jasmonic 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
Jasmonic acid,1TBDMS,isomer #1	CC/C=C\C[C@H]1C(=O)CC[C@@H]1CC(=O)O[Si](C)(C)C(C)(C)C	2017.5	Semi standard non polar	33892256
Jasmonic acid,1TBDMS,isomer #2	CC/C=C\CC1=C(O[Si](C)(C)C(C)(C)C)CC[C@@H]1CC(=O)O	2117.4	Semi standard non polar	33892256
Jasmonic acid,1TBDMS,isomer #3	CC/C=C\C[C@H]1C(O[Si](C)(C)C(C)(C)C)=CC[C@@H]1CC(=O)O	2079.3	Semi standard non polar	33892256
Jasmonic 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
Jasmonic 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
Jasmonic 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
Jasmonic 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

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Jasmonic acid GC-MS (1 TMS)	splash10-0gc1-3910000000-fc5414b8972660237107	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Jasmonic acid GC-MS (2 TMS)	splash10-00di-1960000000-15b13e2686e63dbec8ac	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Jasmonic acid GC-MS (1 MEOX; 1 TMS)	splash10-0fur-5920000000-56a3bfca05d9c2a0fb58	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Jasmonic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-053r-6900000000-6dbc88cef2dd120798d4	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Jasmonic acid GC-MS (1 TMS) - 70eV, Positive	splash10-0fy9-9450000000-0d94fd142631685c4b7b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Jasmonic acid 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Jasmonic acid NA 35V, negative-QTOF	splash10-0a4i-9000000000-2d9af7143ec50cf2d0d0	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Jasmonic acid LC-ESI-QTOF 35V, negative-QTOF	splash10-0a4i-9000000000-2d9af7143ec50cf2d0d0	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Jasmonic acid NA , negative-QTOF	splash10-066r-2930000000-fa66a377eb1b1fca8f5c	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Jasmonic acid n/a 14V, negative-QTOF	splash10-014i-0900000000-6a243c2851549d3933a0	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Jasmonic acid n/a 14V, negative-QTOF	splash10-0a4i-0090000000-32f15e4d1ce43554b369	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Jasmonic acid Orbitrap 0V, negative-QTOF	splash10-0a4i-1090000000-0eea64532a321522940a	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Jasmonic acid Orbitrap 1V, negative-QTOF	splash10-0a4i-1090000000-dcd76ae3b160ae066dac	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Jasmonic acid Orbitrap 1V, negative-QTOF	splash10-0a4i-1090000000-04497dd8bc966faba21c	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Jasmonic acid Orbitrap 2V, negative-QTOF	splash10-0a4i-2090000000-1aa739b17227b8175964	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Jasmonic acid Orbitrap 2V, negative-QTOF	splash10-0a4i-2090000000-c3df319b32792e702631	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Jasmonic acid Orbitrap 2V, negative-QTOF	splash10-0a4i-4090000000-aa4a7a821d19b44f0cd5	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Jasmonic acid Orbitrap 3V, negative-QTOF	splash10-0a4i-5090000000-82f8a4dbefd75fc32972	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Jasmonic acid Orbitrap 3V, negative-QTOF	splash10-0a4i-6090000000-910ea32926dde4e482cb	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Jasmonic acid Orbitrap 4V, negative-QTOF	splash10-0a4i-9080000000-56dfbbb726baa8bf1ca7	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Jasmonic acid Orbitrap 5V, negative-QTOF	splash10-0a4i-9030000000-a7e12bbe5010ba971a9c	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Jasmonic acid Orbitrap 6V, negative-QTOF	splash10-0a4i-9010000000-8184a91f4d8f167c8442	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Jasmonic acid Orbitrap 7V, negative-QTOF	splash10-0a4i-9000000000-dcce12c198d67bee2dbe	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Jasmonic acid Orbitrap 9V, negative-QTOF	splash10-0a4i-9000000000-47b37bf1431de1c71ac6	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Jasmonic acid Orbitrap 13V, negative-QTOF	splash10-0a4i-9000000000-b8485c47ca16500d47c9	2020-07-22	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Jasmonic acid 10V, Positive-QTOF	splash10-03dl-1940000000-cbdd7749a0552b6dcb18	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Jasmonic acid 20V, Positive-QTOF	splash10-015c-9700000000-4b9efb60332c4d520667	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Jasmonic acid 40V, Positive-QTOF	splash10-0f9x-9100000000-e7e90e131d7ac7d27a35	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Jasmonic acid 10V, Negative-QTOF	splash10-0aor-0690000000-d03d837380060d855a00	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Jasmonic acid 20V, Negative-QTOF	splash10-0aor-3950000000-30695cc3cca6390fcace	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Jasmonic acid 40V, Negative-QTOF	splash10-0a4m-9400000000-c0d8ea2d3164bace07b2	2016-08-03	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Jasmonic_acid

METLIN ID

Not Available

PubChem Compound

5281166

PDB ID

Not Available

ChEBI ID

18292

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1459291

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Rossard S, Roblin G, Atanassova R: Ergosterol triggers characteristic elicitation steps in Beta vulgaris leaf tissues. J Exp Bot. 2010 Jun;61(6):1807-16. doi: 10.1093/jxb/erq047. Epub 2010 Mar 19. [PubMed:20304987 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Jasmonic acid (HMDB0032797)

MOL for HMDB0032797 (Jasmonic acid)

3D MOL for HMDB0032797 (Jasmonic acid)

3D SDF for HMDB0032797 (Jasmonic acid)

3D-SDF for HMDB0032797 (Jasmonic acid)

PDB for HMDB0032797 (Jasmonic acid)

3D PDB for HMDB0032797 (Jasmonic acid)

SMILES for HMDB0032797 (Jasmonic acid)

INCHI for HMDB0032797 (Jasmonic acid)

Structure for HMDB0032797 (Jasmonic acid)

3D Structure for HMDB0032797 (Jasmonic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra