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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:44:28 UTC

Update Date

2022-03-07 02:54:58 UTC

HMDB ID

HMDB0036583

Secondary Accession Numbers

HMDB36583

Metabolite Identification

Common Name

Methyl jasmonate

Description

Methyl 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 Methyl jasmonate.

Structure

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

HMDB0036583
     RDKit          3D
Methyl jasmonate
 36 36  0  0  0  0  0  0  0  0999 V2000
   -4.6072    2.0299    0.3076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7298    0.8919   -0.2044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5438   -0.1554    0.7948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3789   -0.5148    1.2855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1148    0.1197    0.8655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2169   -0.9484    0.2796 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8192   -1.6105   -0.8853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9833   -1.6370   -1.1760 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2868   -2.2400   -1.6332 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5448   -1.5131   -1.1625 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0459   -0.3707   -0.3035 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0672   -0.0329    0.7547 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2733    0.5280    0.0916 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3333    0.6586   -1.1574 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3760    0.9267    0.8342 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5323    1.4630    0.2157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3756    2.9416   -0.2812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4166    2.1734    1.4000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6863    1.8184    0.1613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3761    0.4196   -1.0260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8473    1.2485   -0.7425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4625   -0.6862    1.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3621   -1.3352    2.0507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5548    0.5332    1.7568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1992    0.9149    0.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0091   -1.7081    1.0557 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1696   -2.1810   -2.7320 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3370   -3.3265   -1.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0932   -2.2175   -0.4893 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1703   -1.1860   -2.0017 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7702    0.4889   -0.9246 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3938   -0.9909    1.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6742    0.6156    1.5401 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2847    0.6734    0.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0327    2.2069    0.8753 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2800    2.0024   -0.7164 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
 15 16  1  0
 11  6  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  1
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  6
 12 32  1  0
 12 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
M  END


  Mrv0541 10111201472D          

 16 16  0  0  0  0            999 V2000
   -0.5948   -2.0223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0404   -1.3793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7437   -0.5715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1876    0.0711    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0127    0.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2432    0.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5515    1.3732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8919    0.8788    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1003    1.1094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5515    2.1973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9135   -1.4461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2765   -2.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0875    1.9127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8771    2.1518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4789    1.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2685    1.8265    0.0000 C   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 11  1  0  0  0  0
  4  5  1  0  0  0  0
  4  8  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 10  2  0  0  0  0
  8  9  1  6  0  0  0
 11 12  1  0  0  0  0
  4  3  1  1  0  0  0
  9 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036583

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C13H20O3/c1-3-4-5-6-11-10(7-8-12(11)14)9-13(15)16-2/h4-5,10-11H,3,6-9H2,1-2H3/b5-4-/t10-,11-/m1/s1

> <INCHI_KEY>
GEWDNTWNSAZUDX-WQMVXFAESA-N

> <FORMULA>
C13H20O3

> <MOLECULAR_WEIGHT>
224.2961

> <EXACT_MASS>
224.141244506

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
25.025688758104607

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 2-[(1R,2R)-3-oxo-2-[(2Z)-pent-2-en-1-yl]cyclopentyl]acetate

> <ALOGPS_LOGP>
2.62

> <JCHEM_LOGP>
2.560204933666667

> <ALOGPS_LOGS>
-3.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.880354377682645

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
63.3256

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.68e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(-)-methyl jasmonate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036583
     RDKit          3D
Methyl jasmonate
 36 36  0  0  0  0  0  0  0  0999 V2000
   -4.6072    2.0299    0.3076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7298    0.8919   -0.2044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5438   -0.1554    0.7948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3789   -0.5148    1.2855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1148    0.1197    0.8655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2169   -0.9484    0.2796 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8192   -1.6105   -0.8853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9833   -1.6370   -1.1760 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2868   -2.2400   -1.6332 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5448   -1.5131   -1.1625 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0459   -0.3707   -0.3035 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0672   -0.0329    0.7547 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2733    0.5280    0.0916 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3333    0.6586   -1.1574 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3760    0.9267    0.8342 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5323    1.4630    0.2157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3756    2.9416   -0.2812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4166    2.1734    1.4000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6863    1.8184    0.1613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3761    0.4196   -1.0260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8473    1.2485   -0.7425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4625   -0.6862    1.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3621   -1.3352    2.0507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5548    0.5332    1.7568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1992    0.9149    0.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0091   -1.7081    1.0557 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1696   -2.1810   -2.7320 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3370   -3.3265   -1.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0932   -2.2175   -0.4893 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1703   -1.1860   -2.0017 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7702    0.4889   -0.9246 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3938   -0.9909    1.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6742    0.6156    1.5401 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2847    0.6734    0.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0327    2.2069    0.8753 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2800    2.0024   -0.7164 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
 15 16  1  0
 11  6  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  1
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  6
 12 32  1  0
 12 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
M  END

HEADER    PROTEIN                                 11-OCT-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-OCT-12         0                                  
HETATM    1  O   UNK     0      -1.110  -3.775   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.942  -2.575   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.388  -1.067   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.217   0.133   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.757   0.132   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.187   1.610   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.896   2.563   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.665   1.640   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.187   2.071   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.896   4.102   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -3.572  -2.699   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -4.249  -4.115   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.163   3.570   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.637   4.017   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.761   2.963   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.235   3.409   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    5    8    3                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    4    7    9                                                  
CONECT    9    8   13                                                       
CONECT   10    7                                                            
CONECT   11    2   12                                                       
CONECT   12   11                                                            
CONECT   13    9   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    HMDB0036583
HETATM    1  C1  UNL     1      -4.607   2.030   0.308  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.730   0.892  -0.204  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.544  -0.155   0.795  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.379  -0.515   1.286  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.115   0.120   0.865  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.217  -0.948   0.280  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.819  -1.610  -0.885  1.00  0.00           C  
HETATM    8  O1  UNL     1      -1.983  -1.637  -1.176  1.00  0.00           O  
HETATM    9  C8  UNL     1       0.287  -2.240  -1.633  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.545  -1.513  -1.162  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.046  -0.371  -0.303  1.00  0.00           C  
HETATM   12  C11 UNL     1       2.067  -0.033   0.755  1.00  0.00           C  
HETATM   13  C12 UNL     1       3.273   0.528   0.092  1.00  0.00           C  
HETATM   14  O2  UNL     1       3.333   0.659  -1.157  1.00  0.00           O  
HETATM   15  O3  UNL     1       4.376   0.927   0.834  1.00  0.00           O  
HETATM   16  C13 UNL     1       5.532   1.463   0.216  1.00  0.00           C  
HETATM   17  H1  UNL     1      -4.376   2.942  -0.281  1.00  0.00           H  
HETATM   18  H2  UNL     1      -4.417   2.173   1.400  1.00  0.00           H  
HETATM   19  H3  UNL     1      -5.686   1.818   0.161  1.00  0.00           H  
HETATM   20  H4  UNL     1      -4.376   0.420  -1.026  1.00  0.00           H  
HETATM   21  H5  UNL     1      -2.847   1.249  -0.743  1.00  0.00           H  
HETATM   22  H6  UNL     1      -4.462  -0.686   1.165  1.00  0.00           H  
HETATM   23  H7  UNL     1      -2.362  -1.335   2.051  1.00  0.00           H  
HETATM   24  H8  UNL     1      -0.555   0.533   1.757  1.00  0.00           H  
HETATM   25  H9  UNL     1      -1.199   0.915   0.134  1.00  0.00           H  
HETATM   26  H10 UNL     1       0.009  -1.708   1.056  1.00  0.00           H  
HETATM   27  H11 UNL     1       0.170  -2.181  -2.732  1.00  0.00           H  
HETATM   28  H12 UNL     1       0.337  -3.326  -1.366  1.00  0.00           H  
HETATM   29  H13 UNL     1       2.093  -2.218  -0.489  1.00  0.00           H  
HETATM   30  H14 UNL     1       2.170  -1.186  -2.002  1.00  0.00           H  
HETATM   31  H15 UNL     1       0.770   0.489  -0.925  1.00  0.00           H  
HETATM   32  H16 UNL     1       2.394  -0.991   1.229  1.00  0.00           H  
HETATM   33  H17 UNL     1       1.674   0.616   1.540  1.00  0.00           H  
HETATM   34  H18 UNL     1       6.285   0.673   0.005  1.00  0.00           H  
HETATM   35  H19 UNL     1       6.033   2.207   0.875  1.00  0.00           H  
HETATM   36  H20 UNL     1       5.280   2.002  -0.716  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3   20   21
CONECT    3    4    4   22
CONECT    4    5   23
CONECT    5    6   24   25
CONECT    6    7   11   26
CONECT    7    8    8    9
CONECT    9   10   27   28
CONECT   10   11   29   30
CONECT   11   12   31
CONECT   12   13   32   33
CONECT   13   14   14   15
CONECT   15   16
CONECT   16   34   35   36
END

HMDB0036583
     RDKit          3D
Methyl jasmonate
 36 36  0  0  0  0  0  0  0  0999 V2000
   -4.6072    2.0299    0.3076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7298    0.8919   -0.2044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5438   -0.1554    0.7948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3789   -0.5148    1.2855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1148    0.1197    0.8655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2169   -0.9484    0.2796 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8192   -1.6105   -0.8853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9833   -1.6370   -1.1760 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2868   -2.2400   -1.6332 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5448   -1.5131   -1.1625 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0459   -0.3707   -0.3035 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0672   -0.0329    0.7547 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2733    0.5280    0.0916 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3333    0.6586   -1.1574 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3760    0.9267    0.8342 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5323    1.4630    0.2157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3756    2.9416   -0.2812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4166    2.1734    1.4000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6863    1.8184    0.1613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3761    0.4196   -1.0260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8473    1.2485   -0.7425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4625   -0.6862    1.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3621   -1.3352    2.0507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5548    0.5332    1.7568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1992    0.9149    0.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0091   -1.7081    1.0557 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1696   -2.1810   -2.7320 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3370   -3.3265   -1.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0932   -2.2175   -0.4893 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1703   -1.1860   -2.0017 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7702    0.4889   -0.9246 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3938   -0.9909    1.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6742    0.6156    1.5401 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2847    0.6734    0.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0327    2.2069    0.8753 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2800    2.0024   -0.7164 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
 15 16  1  0
 11  6  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  1
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  6
 12 32  1  0
 12 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-oxo-2-(2-Pentenyl)cyclopentaneacetic acid methyl ester	ChEBI
Methyl (-)-jasmonate	ChEBI
(-)-Methyl jasmonate	Kegg
3-oxo-2-(2-Pentenyl)cyclopentaneacetate methyl ester	Generator
Methyl (-)-jasmonic acid	Generator
(-)-Methyl jasmonic acid	Generator
Methyl jasmonic acid	Generator
(-)-Jasmonic acid methyl ester	HMDB
(3R,7R)-Methyl jasmonate	HMDB
FEMA 3410	HMDB
Jasmonic acid methyl ester	HMDB
Methyl (2-pent-2-enyl-3-oxo-1-cyclopentyl)acetate	HMDB
Methyl 3-oxo-2-(2-pentenyl)cyclopentaneacetate	HMDB
Methyl cis-jasmonate	HMDB
Z-Methyl jasmonoate	HMDB
Methyl epijasmonate	MeSH, HMDB

Chemical Formula

C₁₃H₂₀O₃

Average Molecular Weight

224.2961

Monoisotopic Molecular Weight

224.141244506

IUPAC Name

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

Traditional Name

(-)-methyl jasmonate

CAS Registry Number

1211-29-6

SMILES

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

InChI Identifier

InChI=1S/C13H20O3/c1-3-4-5-6-11-10(7-8-12(11)14)9-13(15)16-2/h4-5,10-11H,3,6-9H2,1-2H3/b5-4-/t10-,11-/m1/s1

InChI Key

GEWDNTWNSAZUDX-WQMVXFAESA-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
Methyl ester
Cyclic ketone
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

methyl ester (CHEBI:15929 )
jasmonate ester (CHEBI:15929 )
Jasmonic acids (C11512 )
Jasmonic acids (LMFA02020010 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	25 °C	Not Available
Boiling Point	110.00 °C. @ 0.20 mm Hg	The Good Scents Company Information System
Water Solubility	0 slightly	The Good Scents Company Information System
LogP	2.945 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.17 g/L	ALOGPS
logP	2.62	ALOGPS
logP	2.56	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	63.33 m³·mol⁻¹	ChemAxon
Polarizability	25.03 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]+	156.848	31661259
DarkChem	[M-H]-	149.714	31661259
DeepCCS	[M+H]+	157.458	30932474
DeepCCS	[M-H]-	155.063	30932474
DeepCCS	[M-2H]-	187.947	30932474
DeepCCS	[M+Na]+	163.471	30932474
AllCCS	[M+H]+	154.5	32859911
AllCCS	[M+H-H2O]+	150.8	32859911
AllCCS	[M+NH4]+	157.9	32859911
AllCCS	[M+Na]+	158.9	32859911
AllCCS	[M-H]-	157.7	32859911
AllCCS	[M+Na-2H]-	158.4	32859911
AllCCS	[M+HCOO]-	159.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Methyl jasmonate	CC\C=C/C[C@@H]1[C@@H](CC(=O)OC)CCC1=O	2376.5	Standard polar	33892256
Methyl jasmonate	CC\C=C/C[C@@H]1[C@@H](CC(=O)OC)CCC1=O	1621.5	Standard non polar	33892256
Methyl jasmonate	CC\C=C/C[C@@H]1[C@@H](CC(=O)OC)CCC1=O	1658.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Methyl jasmonate,1TMS,isomer #1	CC/C=C\CC1=C(O[Si](C)(C)C)CC[C@@H]1CC(=O)OC	1773.3	Semi standard non polar	33892256
Methyl jasmonate,1TMS,isomer #1	CC/C=C\CC1=C(O[Si](C)(C)C)CC[C@@H]1CC(=O)OC	1780.9	Standard non polar	33892256
Methyl jasmonate,1TMS,isomer #2	CC/C=C\C[C@H]1C(O[Si](C)(C)C)=CC[C@@H]1CC(=O)OC	1758.2	Semi standard non polar	33892256
Methyl jasmonate,1TMS,isomer #2	CC/C=C\C[C@H]1C(O[Si](C)(C)C)=CC[C@@H]1CC(=O)OC	1786.3	Standard non polar	33892256
Methyl jasmonate,1TBDMS,isomer #1	CC/C=C\CC1=C(O[Si](C)(C)C(C)(C)C)CC[C@@H]1CC(=O)OC	2001.4	Semi standard non polar	33892256
Methyl jasmonate,1TBDMS,isomer #1	CC/C=C\CC1=C(O[Si](C)(C)C(C)(C)C)CC[C@@H]1CC(=O)OC	1978.1	Standard non polar	33892256
Methyl jasmonate,1TBDMS,isomer #2	CC/C=C\C[C@H]1C(O[Si](C)(C)C(C)(C)C)=CC[C@@H]1CC(=O)OC	1978.4	Semi standard non polar	33892256
Methyl jasmonate,1TBDMS,isomer #2	CC/C=C\C[C@H]1C(O[Si](C)(C)C(C)(C)C)=CC[C@@H]1CC(=O)OC	1925.2	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Methyl jasmonate GC-MS (Non-derivatized)	splash10-0036-6900000000-e2a3f1c368618b3e5f44	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl jasmonate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0aos-6900000000-0277b3467bce13283ff1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl jasmonate 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 - Methyl jasmonate LC-ESI-QTOF , negative-QTOF	splash10-00di-1190000000-943fc4cad10af285a2be	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methyl jasmonate LC-ESI-QTOF , negative-QTOF	splash10-002b-6910000000-b3add72153d54084414b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methyl jasmonate 30V, Negative-QTOF	splash10-002b-6910000000-b3add72153d54084414b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methyl jasmonate 30V, Positive-QTOF	splash10-002b-6910000000-f1bcd33a3f20473d55ab	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl jasmonate 10V, Positive-QTOF	splash10-004l-1950000000-3c4a847eb81b54960c7b	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl jasmonate 20V, Positive-QTOF	splash10-05rr-9710000000-500c8cdfcf8ef9dc46d1	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl jasmonate 40V, Positive-QTOF	splash10-0f9x-9100000000-6ebb500b1e7a59d8c7e8	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl jasmonate 10V, Negative-QTOF	splash10-00di-0490000000-c565f5ccca764f993aa0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl jasmonate 20V, Negative-QTOF	splash10-00dl-4980000000-9c08c7091ed7d3a39d47	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl jasmonate 40V, Negative-QTOF	splash10-006x-8900000000-0e54fbfd7224fd3d6d2f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl jasmonate 10V, Negative-QTOF	splash10-00di-8090000000-33319c51557d092716f4	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl jasmonate 20V, Negative-QTOF	splash10-006x-9210000000-740f7074694405f5de2c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl jasmonate 40V, Negative-QTOF	splash10-0006-9200000000-25e9eab4222f102fe057	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl jasmonate 10V, Positive-QTOF	splash10-0kea-2940000000-29e9828c7230abaacf6b	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl jasmonate 20V, Positive-QTOF	splash10-053s-6900000000-04d6ddc8ffb62ec14cd6	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl jasmonate 40V, Positive-QTOF	splash10-057l-9100000000-f913cbf151b98b42e7a8	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Methyl_jasmonate

METLIN ID

Not Available

PubChem Compound

5367719

PDB ID

Not Available

ChEBI ID

15929

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1000141

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Umukoro S, Olugbemide AS: Antinociceptive effects of methyl jasmonate in experimental animals. J Nat Med. 2011 Jul;65(3-4):466-70. doi: 10.1007/s11418-011-0520-3. Epub 2011 Mar 9. [PubMed:21387099 ]
Pi Y, Liao Z, Jiang K, Huang B, Deng Z, Zhao D, Zeng H, Sun X, Tang K: Molecular cloning, characterization and expression of a jasmonate biosynthetic pathway gene encoding allene oxide cyclase from Camptotheca acuminata. Biosci Rep. 2008 Dec;28(6):349-55. doi: 10.1042/BSR20060001. [PubMed:18847436 ]
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 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Methyl jasmonate (HMDB0036583)

MOL for HMDB0036583 (Methyl jasmonate)

3D MOL for HMDB0036583 (Methyl jasmonate)

3D SDF for HMDB0036583 (Methyl jasmonate)

3D-SDF for HMDB0036583 (Methyl jasmonate)

PDB for HMDB0036583 (Methyl jasmonate)

3D PDB for HMDB0036583 (Methyl jasmonate)

SMILES for HMDB0036583 (Methyl jasmonate)

INCHI for HMDB0036583 (Methyl jasmonate)

Structure for HMDB0036583 (Methyl jasmonate)

3D Structure for HMDB0036583 (Methyl jasmonate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra