MiMeDB: Showing metabocard for jasmonate (MMDBc0054521)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-05 23:16:36 UTC

Update Date

2024-04-30 20:53:59 UTC

Metabolite ID

MMDBc0054521

Metabolite Identification

Common Name

jasmonate

Description

Jasmonic acid is found in apple. Esters are present in Jasminum grandiflorum (royal jasmine) and are responsible for its odour. Jasmonic acid is a member of the jasmonate class of plant hormones. It is biosynthesized from linolenic acid by the octadecanoid pathway

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>
MMDBc0054521

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₁₂H₁₈O₃

Average Mass

210.2695

Monoisotopic Mass

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

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-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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-0gc1-3910000000-fc5414b8972660237107	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-00di-1960000000-15b13e2686e63dbec8ac	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)	splash10-0fur-5920000000-56a3bfca05d9c2a0fb58	2014-06-16	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-053r-6900000000-6dbc88cef2dd120798d4	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0fy9-9450000000-0d94fd142631685c4b7b	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - NA 35V, negative	splash10-0a4i-9000000000-2d9af7143ec50cf2d0d0	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 35V, negative	splash10-0a4i-9000000000-2d9af7143ec50cf2d0d0	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - NA , negative	splash10-066r-2930000000-fa66a377eb1b1fca8f5c	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 14V, negative	splash10-014i-0900000000-6a243c2851549d3933a0	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 14V, negative	splash10-0a4i-0090000000-32f15e4d1ce43554b369	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 0V, negative	splash10-0a4i-1090000000-0eea64532a321522940a	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, negative	splash10-0a4i-1090000000-dcd76ae3b160ae066dac	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, negative	splash10-0a4i-1090000000-04497dd8bc966faba21c	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-0a4i-2090000000-1aa739b17227b8175964	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-0a4i-2090000000-c3df319b32792e702631	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-0a4i-4090000000-aa4a7a821d19b44f0cd5	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, negative	splash10-0a4i-5090000000-82f8a4dbefd75fc32972	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, negative	splash10-0a4i-6090000000-910ea32926dde4e482cb	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, negative	splash10-0a4i-9080000000-56dfbbb726baa8bf1ca7	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, negative	splash10-0a4i-9030000000-a7e12bbe5010ba971a9c	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, negative	splash10-0a4i-9010000000-8184a91f4d8f167c8442	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 7V, negative	splash10-0a4i-9000000000-dcce12c198d67bee2dbe	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 9V, negative	splash10-0a4i-9000000000-47b37bf1431de1c71ac6	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 13V, negative	splash10-0a4i-9000000000-b8485c47ca16500d47c9	2020-07-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03dl-1940000000-cbdd7749a0552b6dcb18	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-015c-9700000000-4b9efb60332c4d520667	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f9x-9100000000-e7e90e131d7ac7d27a35	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0aor-0690000000-d03d837380060d855a00	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0aor-3950000000-30695cc3cca6390fcace	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4m-9400000000-c0d8ea2d3164bace07b2	2016-08-03	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0016491	Hydrogen Ion	(1R,2R)-12-hydroxyjasmonate	Jasmonate monooxygenase ABM	Oxygenation	RHEA	34755880
MMDBr0016492	Hydrogen Ion	(1R,2R)-12-hydroxyjasmonate	Jasmonate monooxygenase ABM	Oxygenation	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	5	Human feces
Eukaryota/Fungi	Basidiomycota	8	Human feces

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0032797

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

References

Synthesis Reference

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. doi: 10.1038/35036052. [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. doi: 10.1194/jlr.R600022-JLR200. 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. doi: 10.1194/jlr.R700005-JLR200. 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 ]
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 ]
Yannai, Shmuel (2004). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. 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 jasmonate (MMDBc0054521)

MOL for #<Metabolite:0x0000564aef825ab0>

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3D PDB for #<Metabolite:0x0000564aef825ab0>

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Structure for #<Metabolite:0x0000564aef825ab0>

3D Structure for #<Metabolite:0x0000564aef825ab0>