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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-22 21:12:00 UTC

Update Date

2021-09-22 21:12:00 UTC

HMDB ID

HMDB0301800

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Methyl epijasmonate

Description

methyl (+)-7-isojasmonate, also known as (1R,2S)-methyl jasmonate or methyl 7-epi-jasmonic acid, 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 very few articles have been published on methyl (+)-7-isojasmonate.

Structure

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

HMDB0301800
     RDKit          3D
Methyl epijasmonate
 36 36  0  0  0  0  0  0  0  0999 V2000
    4.2238   -0.6296    0.8436 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3663   -1.0569   -0.3696 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0052    0.1381   -1.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7789    0.5418   -1.3260 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6122   -0.1954   -0.8466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2495    0.6344    0.1030 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6277    0.9925    1.2531 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2029    2.0308    1.4431 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6392   -0.2174    2.1207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5072   -1.0875    1.6536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2934   -0.1612    0.7989 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2981   -0.8141   -0.0878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0281    0.2065   -0.8815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5457    0.7358   -1.9125 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3115    0.6432   -0.5226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0211    1.6155   -1.2684 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2310   -0.3862    0.4571 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2258   -1.4361    1.6079 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7700    0.2766    1.2852 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0610   -1.7252   -0.9735 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5999   -1.6877    0.0441 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8075    0.7856   -1.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5991    1.4892   -1.9077 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8351   -1.1844   -0.4741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0316   -0.3716   -1.7736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6660    1.5223   -0.4059 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6092   -0.7518    2.0887 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3867    0.1069    3.1642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1550   -1.9942    1.1006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1605   -1.3893    2.5100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8419    0.5438    1.4710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8587   -1.5206   -0.8095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9865   -1.4031    0.5508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4632    2.3132   -0.4972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3447    2.2665   -1.8701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8186    1.1698   -1.8964 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  6
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  1
 12 32  1  0
 12 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
M  END


  Mrv0541 10111201452D          

 16 16  0  0  1  0            999 V2000
    0.9641   -0.6548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7846   -0.5685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2696   -1.2360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1202    0.1852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6353    0.8526    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8902    1.6372    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2228    2.1222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2228    2.9472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5553    1.6373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8103    0.8526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6748    1.8922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8463    2.6991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6309    2.9541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0900   -1.1497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2440    2.4021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0286    2.6570    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  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
  6 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  3 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0301800

> <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-KWKBKKAHSA-N

> <FORMULA>
C13H20O3

> <MOLECULAR_WEIGHT>
224.2961

> <EXACT_MASS>
224.141244506

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
25.201511264433073

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 2-[(1R,2S)-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 7-epi-jasmonate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0301800
     RDKit          3D
Methyl epijasmonate
 36 36  0  0  0  0  0  0  0  0999 V2000
    4.2238   -0.6296    0.8436 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3663   -1.0569   -0.3696 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0052    0.1381   -1.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7789    0.5418   -1.3260 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6122   -0.1954   -0.8466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2495    0.6344    0.1030 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6277    0.9925    1.2531 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2029    2.0308    1.4431 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6392   -0.2174    2.1207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5072   -1.0875    1.6536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2934   -0.1612    0.7989 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2981   -0.8141   -0.0878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0281    0.2065   -0.8815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5457    0.7358   -1.9125 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3115    0.6432   -0.5226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0211    1.6155   -1.2684 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2310   -0.3862    0.4571 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2258   -1.4361    1.6079 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7700    0.2766    1.2852 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0610   -1.7252   -0.9735 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5999   -1.6877    0.0441 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8075    0.7856   -1.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5991    1.4892   -1.9077 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8351   -1.1844   -0.4741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0316   -0.3716   -1.7736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6660    1.5223   -0.4059 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6092   -0.7518    2.0887 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3867    0.1069    3.1642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1550   -1.9942    1.1006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1605   -1.3893    2.5100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8419    0.5438    1.4710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8587   -1.5206   -0.8095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9865   -1.4031    0.5508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4632    2.3132   -0.4972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3447    2.2665   -1.8701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8186    1.1698   -1.8964 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  6
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  1
 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       1.800  -1.222   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.331  -1.061   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.237  -2.307   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       3.958   0.346   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.053   1.592   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.528   3.056   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.283   3.961   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.283   5.501   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.037   3.056   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.513   1.592   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.993   3.532   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.313   5.038   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.778   5.514   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.768  -2.146   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.922   4.484   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.387   4.960   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2   14                                                       
CONECT    4    2    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9    5                                                       
CONECT   11    6   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   15                                                       
CONECT   14    3                                                            
CONECT   15   13   16                                                       
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0301800
HETATM    1  C1  UNL     1       4.224  -0.630   0.844  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.366  -1.057  -0.370  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.005   0.138  -1.102  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.779   0.542  -1.326  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.612  -0.195  -0.847  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.250   0.634   0.103  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.628   0.993   1.253  1.00  0.00           C  
HETATM    8  O1  UNL     1       1.203   2.031   1.443  1.00  0.00           O  
HETATM    9  C8  UNL     1       0.639  -0.217   2.121  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.507  -1.088   1.654  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.293  -0.161   0.799  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.298  -0.814  -0.088  1.00  0.00           C  
HETATM   13  C12 UNL     1      -3.028   0.206  -0.882  1.00  0.00           C  
HETATM   14  O2  UNL     1      -2.546   0.736  -1.912  1.00  0.00           O  
HETATM   15  O3  UNL     1      -4.312   0.643  -0.523  1.00  0.00           O  
HETATM   16  C13 UNL     1      -5.021   1.615  -1.268  1.00  0.00           C  
HETATM   17  H1  UNL     1       5.231  -0.386   0.457  1.00  0.00           H  
HETATM   18  H2  UNL     1       4.226  -1.436   1.608  1.00  0.00           H  
HETATM   19  H3  UNL     1       3.770   0.277   1.285  1.00  0.00           H  
HETATM   20  H4  UNL     1       4.061  -1.725  -0.973  1.00  0.00           H  
HETATM   21  H5  UNL     1       2.600  -1.688   0.044  1.00  0.00           H  
HETATM   22  H6  UNL     1       3.808   0.786  -1.520  1.00  0.00           H  
HETATM   23  H7  UNL     1       1.599   1.489  -1.908  1.00  0.00           H  
HETATM   24  H8  UNL     1       0.835  -1.184  -0.474  1.00  0.00           H  
HETATM   25  H9  UNL     1      -0.032  -0.372  -1.774  1.00  0.00           H  
HETATM   26  H10 UNL     1      -0.666   1.522  -0.406  1.00  0.00           H  
HETATM   27  H11 UNL     1       1.609  -0.752   2.089  1.00  0.00           H  
HETATM   28  H12 UNL     1       0.387   0.107   3.164  1.00  0.00           H  
HETATM   29  H13 UNL     1      -0.155  -1.994   1.101  1.00  0.00           H  
HETATM   30  H14 UNL     1      -1.160  -1.389   2.510  1.00  0.00           H  
HETATM   31  H15 UNL     1      -1.842   0.544   1.471  1.00  0.00           H  
HETATM   32  H16 UNL     1      -1.859  -1.521  -0.810  1.00  0.00           H  
HETATM   33  H17 UNL     1      -2.986  -1.403   0.551  1.00  0.00           H  
HETATM   34  H18 UNL     1      -5.463   2.313  -0.497  1.00  0.00           H  
HETATM   35  H19 UNL     1      -4.345   2.267  -1.870  1.00  0.00           H  
HETATM   36  H20 UNL     1      -5.819   1.170  -1.896  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

HMDB0301800
     RDKit          3D
Methyl epijasmonate
 36 36  0  0  0  0  0  0  0  0999 V2000
    4.2238   -0.6296    0.8436 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3663   -1.0569   -0.3696 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0052    0.1381   -1.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7789    0.5418   -1.3260 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6122   -0.1954   -0.8466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2495    0.6344    0.1030 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6277    0.9925    1.2531 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2029    2.0308    1.4431 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6392   -0.2174    2.1207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5072   -1.0875    1.6536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2934   -0.1612    0.7989 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2981   -0.8141   -0.0878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0281    0.2065   -0.8815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5457    0.7358   -1.9125 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3115    0.6432   -0.5226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0211    1.6155   -1.2684 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2310   -0.3862    0.4571 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2258   -1.4361    1.6079 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7700    0.2766    1.2852 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0610   -1.7252   -0.9735 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5999   -1.6877    0.0441 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8075    0.7856   -1.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5991    1.4892   -1.9077 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8351   -1.1844   -0.4741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0316   -0.3716   -1.7736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6660    1.5223   -0.4059 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6092   -0.7518    2.0887 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3867    0.1069    3.1642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1550   -1.9942    1.1006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1605   -1.3893    2.5100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8419    0.5438    1.4710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8587   -1.5206   -0.8095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9865   -1.4031    0.5508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4632    2.3132   -0.4972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3447    2.2665   -1.8701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8186    1.1698   -1.8964 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  6
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  1
 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
(+)-7-Isojasmonic acid methyl ester	ChEBI
(1R,2S)-Methyl jasmonate	ChEBI
(3R,7S)-Methyl jasmonate	ChEBI
Methyl 7-epi-jasmonate	ChEBI
(+)-7-Isojasmonate methyl ester	Generator
(1R,2S)-Methyl jasmonic acid	Generator
(3R,7S)-Methyl jasmonic acid	Generator
Methyl 7-epi-jasmonic acid	Generator
Methyl (+)-7-isojasmonic acid	Generator
Methyl epijasmonic acid	Generator
Jasmonic acid methyl ester	MeSH
Methyl jasmonate	MeSH
3-oxo-2-(2-Pentenyl)cyclopentaneacetic acid methyl ester	MeSH

Chemical Formula

C₁₃H₂₀O₃

Average Molecular Weight

224.2961

Monoisotopic Molecular Weight

224.141244506

IUPAC Name

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

Traditional Name

methyl 7-epi-jasmonate

CAS Registry Number

95722-42-2

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-KWKBKKAHSA-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:25242 )
jasmonate ester (CHEBI:25242 )
Jasmonic acids (C16318 )
Jasmonic acids (LMFA02020016 )

Ontology

Physiological effect

Organoleptic effect

Odor

Jasmine

Disposition

Source

Exogenous

Exogenous (HMDB: HMDB0301800)

Food

Fruit

Citrus

Lemon (FooDB: FOOD00054)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	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	25.2 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]+	154.466	32859911
AllCCS	[M+H-H2O]+	150.762	32859911
AllCCS	[M+Na]+	158.898	32859911
AllCCS	[M+NH4]+	157.908	32859911
AllCCS	[M-H]-	157.653	32859911
AllCCS	[M+Na-2H]-	158.39	32859911
AllCCS	[M+HCOO]-	159.307	32859911
DeepCCS	[M+H]+	157.804	30932474
DeepCCS	[M-H]-	155.409	30932474
DeepCCS	[M-2H]-	188.292	30932474
DeepCCS	[M+Na]+	163.805	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	14.9923 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.84 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2145.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	363.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	169.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	207.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	177.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	576.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	491.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	71.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1284.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	433.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1157.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	377.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	396.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	332.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	364.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.5 seconds	40023050

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Methyl epijasmonate,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 epijasmonate,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 epijasmonate,1TMS,isomer #1	CC/C=C\CC1=C(O[Si](C)(C)C)CC[C@@H]1CC(=O)OC	2166.0	Standard polar	33892256
Methyl epijasmonate,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 epijasmonate,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 epijasmonate,1TMS,isomer #2	CC/C=C\C[C@@H]1C(O[Si](C)(C)C)=CC[C@@H]1CC(=O)OC	2205.9	Standard polar	33892256
Methyl epijasmonate,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 epijasmonate,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 epijasmonate,1TBDMS,isomer #1	CC/C=C\CC1=C(O[Si](C)(C)C(C)(C)C)CC[C@@H]1CC(=O)OC	2298.0	Standard polar	33892256
Methyl epijasmonate,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 epijasmonate,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
Methyl epijasmonate,1TBDMS,isomer #2	CC/C=C\C[C@@H]1C(O[Si](C)(C)C(C)(C)C)=CC[C@@H]1CC(=O)OC	2317.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl epijasmonate GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2022-08-08	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl epijasmonate 10V, Positive-QTOF	splash10-004l-1950000000-3c4a847eb81b54960c7b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl epijasmonate 20V, Positive-QTOF	splash10-05rr-9710000000-500c8cdfcf8ef9dc46d1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl epijasmonate 40V, Positive-QTOF	splash10-0f9x-9100000000-6ebb500b1e7a59d8c7e8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl epijasmonate 10V, Negative-QTOF	splash10-00di-0490000000-c565f5ccca764f993aa0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl epijasmonate 20V, Negative-QTOF	splash10-00dl-4980000000-9c08c7091ed7d3a39d47	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl epijasmonate 40V, Negative-QTOF	splash10-006x-8900000000-0e54fbfd7224fd3d6d2f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl epijasmonate 10V, Positive-QTOF	splash10-0kea-2940000000-29e9828c7230abaacf6b	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl epijasmonate 20V, Positive-QTOF	splash10-053s-6900000000-04d6ddc8ffb62ec14cd6	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl epijasmonate 40V, Positive-QTOF	splash10-057l-9100000000-f913cbf151b98b42e7a8	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl epijasmonate 10V, Negative-QTOF	splash10-00di-8090000000-33319c51557d092716f4	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl epijasmonate 20V, Negative-QTOF	splash10-006x-9210000000-740f7074694405f5de2c	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl epijasmonate 40V, Negative-QTOF	splash10-0006-9200000000-9de06af8d45f4ade0eb8	2021-10-21	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-18	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

FDB001424

KNApSAcK ID

Not Available

Chemspider ID

4933379

KEGG Compound ID

C16318

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6427970

PDB ID

Not Available

ChEBI ID

25242

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 Methyl epijasmonate (HMDB0301800)

MOL for HMDB0301800 (Methyl epijasmonate)

3D MOL for HMDB0301800 (Methyl epijasmonate)

3D SDF for HMDB0301800 (Methyl epijasmonate)

3D-SDF for HMDB0301800 (Methyl epijasmonate)

PDB for HMDB0301800 (Methyl epijasmonate)

3D PDB for HMDB0301800 (Methyl epijasmonate)

SMILES for HMDB0301800 (Methyl epijasmonate)

INCHI for HMDB0301800 (Methyl epijasmonate)

Structure for HMDB0301800 (Methyl epijasmonate)

3D Structure for HMDB0301800 (Methyl epijasmonate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra