MiMeDB: Showing metabocard for (+)-7-iso-jasmonic acid methyl ester (MMDBc0015311)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 06:09:58 UTC

Update Date

2022-08-31 06:39:08 UTC

Metabolite ID

MMDBc0015311

Metabolite Identification

Common Name

(+)-7-iso-jasmonic acid methyl ester

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>
MMDBc0015311

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₁₃H₂₀O₃

Average Mass

224.2961

Monoisotopic Mass

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

Not Available

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted 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	25.2 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004l-1950000000-3c4a847eb81b54960c7b	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05rr-9710000000-500c8cdfcf8ef9dc46d1	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f9x-9100000000-6ebb500b1e7a59d8c7e8	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0490000000-c565f5ccca764f993aa0	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00dl-4980000000-9c08c7091ed7d3a39d47	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-006x-8900000000-0e54fbfd7224fd3d6d2f	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0kea-2940000000-29e9828c7230abaacf6b	2021-10-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-053s-6900000000-04d6ddc8ffb62ec14cd6	2021-10-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-057l-9100000000-f913cbf151b98b42e7a8	2021-10-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-8090000000-33319c51557d092716f4	2021-10-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-006x-9210000000-740f7074694405f5de2c	2021-10-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9200000000-9de06af8d45f4ade0eb8	2021-10-21	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

Not Available

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	1	Human feces	Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Plant	Pericarp	Citrus limon	FooDB	31437929
Plant	Fruit	Citrus limon	FooDB	31437929

Host Biospecimen and Location

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

External Links

HMDB ID

HMDB0301800

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

References

Synthesis Reference

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for (+)-7-iso-jasmonic acid methyl ester (MMDBc0015311)

MOL for #<Metabolite:0x0000564af3acdb60>

3D MOL for #<Metabolite:0x0000564af3acdb60>

3D SDF for #<Metabolite:0x0000564af3acdb60>

3D-SDF for #<Metabolite:0x0000564af3acdb60>

PDB for #<Metabolite:0x0000564af3acdb60>

3D PDB for #<Metabolite:0x0000564af3acdb60>

SMILES for #<Metabolite:0x0000564af3acdb60>

INCHI for #<Metabolite:0x0000564af3acdb60>

Structure for #<Metabolite:0x0000564af3acdb60>

3D Structure for #<Metabolite:0x0000564af3acdb60>