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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:45:08 UTC

Update Date

2022-09-22 18:34:24 UTC

HMDB ID

HMDB0031740

Secondary Accession Numbers

HMDB31740

Metabolite Identification

Common Name

Methyl dihydrojasmonate

Description

Methyl dihydrojasmonate 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 small amount of articles have been published on Methyl dihydrojasmonate.

Structure

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

HMDB0031740
     RDKit          3D
Methyl dihydrojasmonate
 38 38  0  0  0  0  0  0  0  0999 V2000
    4.3426    0.6042   -0.6736 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4865    1.8370   -0.7091 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0428    1.4375   -0.4578 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0283    0.7803    0.9120 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6867    0.3427    1.3142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0368   -0.6392    0.4847 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6032   -1.9521    0.3073 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6629   -2.3202    0.6677 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3910   -2.7340   -0.4401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7146   -2.2157    0.1170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3547   -1.0765    1.0727 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4024   -0.0420    1.1698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8039    0.5388   -0.1118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0264    1.0617   -0.9327 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1638    0.5320   -0.5005 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5422    1.0963   -1.7449 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2291    0.7197   -1.3519 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7203    0.4569    0.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8328   -0.3083   -1.0032 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8359    2.5074    0.1099 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6083    2.3677   -1.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4543    2.3640   -0.4137 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6870    0.7213   -1.2054 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3282    1.6077    1.6174 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8303    0.0288    0.9848 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0342    1.2632    1.3632 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7339   -0.0124    2.3796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2510   -0.2303   -0.5375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2904   -2.4553   -1.5264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3051   -3.8307   -0.3133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2883   -1.8157   -0.7236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2083   -3.0481    0.6700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1731   -1.5784    2.0753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9804    0.7923    1.8021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2834   -0.4623    1.7054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6687    1.1031   -1.7899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1056    2.0962   -1.8500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1574    0.4624   -2.5931 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  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
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  6
  9 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  1
 12 34  1  0
 12 35  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
M  END


  Mrv0541 10111201372D          

 16 16  0  0  0  0            999 V2000
   -0.4119   -1.4262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3453   -1.3569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8138   -0.6791    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9631    2.3980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1802    2.1373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0236    1.3028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2144    1.1207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0581    0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7241    0.0249    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9071   -0.7213    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7682   -0.7564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0286    0.0257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4017    0.4951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4017    1.2775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8399   -2.0620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6749   -1.9578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2 15  1  0  0  0  0
  4  5  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
  9 10  1  0  0  0  0
  9 13  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 15 16  1  0  0  0  0
  9  8  1  6  0  0  0
 10  1  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0031740

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C13H22O3/c1-3-4-5-6-11-10(7-8-12(11)14)9-13(15)16-2/h10-11H,3-9H2,1-2H3/t10-,11-/m1/s1

> <INCHI_KEY>
KVWWIYGFBYDJQC-GHMZBOCLSA-N

> <FORMULA>
C13H22O3

> <MOLECULAR_WEIGHT>
226.312

> <EXACT_MASS>
226.15689457

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
26.232112100766063

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 2-[(1R,2R)-3-oxo-2-pentylcyclopentyl]acetate

> <ALOGPS_LOGP>
2.56

> <JCHEM_LOGP>
2.922126590333333

> <ALOGPS_LOGS>
-3.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.878709455366441

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
62.209

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.23e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 2-[(1R,2R)-3-oxo-2-pentylcyclopentyl]acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0031740
     RDKit          3D
Methyl dihydrojasmonate
 38 38  0  0  0  0  0  0  0  0999 V2000
    4.3426    0.6042   -0.6736 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4865    1.8370   -0.7091 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0428    1.4375   -0.4578 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0283    0.7803    0.9120 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6867    0.3427    1.3142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0368   -0.6392    0.4847 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6032   -1.9521    0.3073 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6629   -2.3202    0.6677 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3910   -2.7340   -0.4401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7146   -2.2157    0.1170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3547   -1.0765    1.0727 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4024   -0.0420    1.1698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8039    0.5388   -0.1118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0264    1.0617   -0.9327 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1638    0.5320   -0.5005 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5422    1.0963   -1.7449 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2291    0.7197   -1.3519 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7203    0.4569    0.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8328   -0.3083   -1.0032 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8359    2.5074    0.1099 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6083    2.3677   -1.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4543    2.3640   -0.4137 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6870    0.7213   -1.2054 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3282    1.6077    1.6174 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8303    0.0288    0.9848 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0342    1.2632    1.3632 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7339   -0.0124    2.3796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2510   -0.2303   -0.5375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2904   -2.4553   -1.5264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3051   -3.8307   -0.3133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2883   -1.8157   -0.7236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2083   -3.0481    0.6700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1731   -1.5784    2.0753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9804    0.7923    1.8021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2834   -0.4623    1.7054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6687    1.1031   -1.7899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1056    2.0962   -1.8500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1574    0.4624   -2.5931 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  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
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  6
  9 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  1
 12 34  1  0
 12 35  1  0
 16 36  1  0
 16 37  1  0
 16 38  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  C   UNK     0      -0.769  -2.662   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.645  -2.533   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.519  -1.268   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       3.664   4.476   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.203   3.990   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.911   2.432   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.400   2.092   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.108   0.533   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.352   0.046   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.693  -1.346   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.301  -1.412   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.787   0.048   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.617   0.924   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.617   2.385   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       1.568  -3.849   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.126  -3.655   0.000  0.00  0.00           C+0
CONECT    1    2   10                                                       
CONECT    2    1    3   15                                                  
CONECT    3    2                                                            
CONECT    4    5                                                            
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9   10   13    8                                                  
CONECT   10    9   11    1                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13    9   12   14                                                  
CONECT   14   13                                                            
CONECT   15    2   16                                                       
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0031740
HETATM    1  C1  UNL     1       4.343   0.604  -0.674  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.487   1.837  -0.709  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.043   1.438  -0.458  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.028   0.780   0.912  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.687   0.343   1.314  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.037  -0.639   0.485  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.603  -1.952   0.307  1.00  0.00           C  
HETATM    8  O1  UNL     1       1.663  -2.320   0.668  1.00  0.00           O  
HETATM    9  C8  UNL     1      -0.391  -2.734  -0.440  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.715  -2.216   0.117  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.355  -1.077   1.073  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.402  -0.042   1.170  1.00  0.00           C  
HETATM   13  C12 UNL     1      -2.804   0.539  -0.112  1.00  0.00           C  
HETATM   14  O2  UNL     1      -2.026   1.062  -0.933  1.00  0.00           O  
HETATM   15  O3  UNL     1      -4.164   0.532  -0.501  1.00  0.00           O  
HETATM   16  C13 UNL     1      -4.542   1.096  -1.745  1.00  0.00           C  
HETATM   17  H1  UNL     1       5.229   0.720  -1.352  1.00  0.00           H  
HETATM   18  H2  UNL     1       4.720   0.457   0.361  1.00  0.00           H  
HETATM   19  H3  UNL     1       3.833  -0.308  -1.003  1.00  0.00           H  
HETATM   20  H4  UNL     1       3.836   2.507   0.110  1.00  0.00           H  
HETATM   21  H5  UNL     1       3.608   2.368  -1.681  1.00  0.00           H  
HETATM   22  H6  UNL     1       1.454   2.364  -0.414  1.00  0.00           H  
HETATM   23  H7  UNL     1       1.687   0.721  -1.205  1.00  0.00           H  
HETATM   24  H8  UNL     1       2.328   1.608   1.617  1.00  0.00           H  
HETATM   25  H9  UNL     1       2.830   0.029   0.985  1.00  0.00           H  
HETATM   26  H10 UNL     1       0.034   1.263   1.363  1.00  0.00           H  
HETATM   27  H11 UNL     1       0.734  -0.012   2.380  1.00  0.00           H  
HETATM   28  H12 UNL     1      -0.251  -0.230  -0.537  1.00  0.00           H  
HETATM   29  H13 UNL     1      -0.290  -2.455  -1.526  1.00  0.00           H  
HETATM   30  H14 UNL     1      -0.305  -3.831  -0.313  1.00  0.00           H  
HETATM   31  H15 UNL     1      -2.288  -1.816  -0.724  1.00  0.00           H  
HETATM   32  H16 UNL     1      -2.208  -3.048   0.670  1.00  0.00           H  
HETATM   33  H17 UNL     1      -1.173  -1.578   2.075  1.00  0.00           H  
HETATM   34  H18 UNL     1      -1.980   0.792   1.802  1.00  0.00           H  
HETATM   35  H19 UNL     1      -3.283  -0.462   1.705  1.00  0.00           H  
HETATM   36  H20 UNL     1      -5.669   1.103  -1.790  1.00  0.00           H  
HETATM   37  H21 UNL     1      -4.106   2.096  -1.850  1.00  0.00           H  
HETATM   38  H22 UNL     1      -4.157   0.462  -2.593  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3   20   21
CONECT    3    4   22   23
CONECT    4    5   24   25
CONECT    5    6   26   27
CONECT    6    7   11   28
CONECT    7    8    8    9
CONECT    9   10   29   30
CONECT   10   11   31   32
CONECT   11   12   33
CONECT   12   13   34   35
CONECT   13   14   14   15
CONECT   15   16
CONECT   16   36   37   38
END

HMDB0031740
     RDKit          3D
Methyl dihydrojasmonate
 38 38  0  0  0  0  0  0  0  0999 V2000
    4.3426    0.6042   -0.6736 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4865    1.8370   -0.7091 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0428    1.4375   -0.4578 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0283    0.7803    0.9120 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6867    0.3427    1.3142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0368   -0.6392    0.4847 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6032   -1.9521    0.3073 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6629   -2.3202    0.6677 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3910   -2.7340   -0.4401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7146   -2.2157    0.1170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3547   -1.0765    1.0727 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4024   -0.0420    1.1698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8039    0.5388   -0.1118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0264    1.0617   -0.9327 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1638    0.5320   -0.5005 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5422    1.0963   -1.7449 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2291    0.7197   -1.3519 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7203    0.4569    0.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8328   -0.3083   -1.0032 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8359    2.5074    0.1099 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6083    2.3677   -1.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4543    2.3640   -0.4137 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6870    0.7213   -1.2054 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3282    1.6077    1.6174 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8303    0.0288    0.9848 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0342    1.2632    1.3632 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7339   -0.0124    2.3796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2510   -0.2303   -0.5375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2904   -2.4553   -1.5264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3051   -3.8307   -0.3133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2883   -1.8157   -0.7236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2083   -3.0481    0.6700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1731   -1.5784    2.0753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9804    0.7923    1.8021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2834   -0.4623    1.7054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6687    1.1031   -1.7899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1056    2.0962   -1.8500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1574    0.4624   -2.5931 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  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
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  6
  9 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  1
 12 34  1  0
 12 35  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Methyl dihydrojasmonic acid	Generator
(-)-Methyl dihydrojasmonate	HMDB
(1R,2R)-Methyl dihydrojasmonate	HMDB
Cyclopentaneacetic acid, 3-oxo-2-pentyl-, methyl ester	HMDB
Dihydrojasmonic acid methyl ester	HMDB
FEMA 3408	HMDB
Hedione	HMDB
Kharismal	HMDB
Methyl (1R-trans)-3-oxo-2-pentylcyclopentaneacetate	HMDB
Methyl (2-pentyl-3-oxocyclopentyl)acetate	HMDB
Methyl (3-oxo-2-pentylcyclopentyl)acetate	HMDB
Methyl 3-oxo-2-pentylcyclopentaneacetate	HMDB
Methyl hydrojasmonate	HMDB
Methyl trans-dihydrojasmonate	HMDB
trans-(-)-Hedione	HMDB
Methyl 2-[(1R,2R)-3-oxo-2-pentylcyclopentyl]acetic acid	Generator

Chemical Formula

C₁₃H₂₂O₃

Average Molecular Weight

226.312

Monoisotopic Molecular Weight

226.15689457

IUPAC Name

methyl 2-[(1R,2R)-3-oxo-2-pentylcyclopentyl]acetate

Traditional Name

methyl 2-[(1R,2R)-3-oxo-2-pentylcyclopentyl]acetate

CAS Registry Number

24851-98-7

SMILES

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

InChI Identifier

InChI=1S/C13H22O3/c1-3-4-5-6-11-10(7-8-12(11)14)9-13(15)16-2/h10-11H,3-9H2,1-2H3/t10-,11-/m1/s1

InChI Key

KVWWIYGFBYDJQC-GHMZBOCLSA-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

Not Available

Ontology

Cellular substructure

Non-excretory biofluid

Biofluid or Excreta

Saliva (PMID: 20809147)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0031740)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031740)

Source

Endogenous

Endogenous (HMDB: HMDB0031740)

Plant

Plant (HMDB: HMDB0031740)

Animal

Animal (HMDB: HMDB0031740)

Exogenous

Food

Food (HMDB: HMDB0031740)

Tea

Exogenous (HMDB: HMDB0031740)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0031740)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0031740)

Lipid metabolism pathway (HMDB: HMDB0031740)

Cellular process

Cell signaling (HMDB: HMDB0031740)

Biochemical process

Lipid transport (HMDB: HMDB0031740)

Role

Biological role

Energy source (HMDB: HMDB0031740)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0031740)

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0031740)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-10 °C	Not Available
Boiling Point	109.00 to 112.00 °C. @ 0.20 mm Hg	The Good Scents Company Information System
Water Solubility	0.28 mg/mL	Not Available
LogP	2.653 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.12 g/L	ALOGPS
logP	2.56	ALOGPS
logP	2.92	ChemAxon
logS	-3.3	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	7	ChemAxon
Refractivity	62.21 m³·mol⁻¹	ChemAxon
Polarizability	26.23 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]+	157.343	31661259
DarkChem	[M-H]-	157.615	31661259
DeepCCS	[M+H]+	158.664	30932474
DeepCCS	[M-H]-	156.306	30932474
DeepCCS	[M-2H]-	189.191	30932474
DeepCCS	[M+Na]+	164.757	30932474
AllCCS	[M+H]+	155.7	32859911
AllCCS	[M+H-H2O]+	152.0	32859911
AllCCS	[M+NH4]+	159.0	32859911
AllCCS	[M+Na]+	160.0	32859911
AllCCS	[M-H]-	159.2	32859911
AllCCS	[M+Na-2H]-	160.0	32859911
AllCCS	[M+HCOO]-	161.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.75 minutes	32390414
Predicted by Siyang on May 30, 2022	16.3834 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.86 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2584.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	491.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	200.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	262.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	349.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	662.6 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	704.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	79.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1437.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	461.0 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	1491.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	366.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	403.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	369.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	380.9 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	20.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Methyl dihydrojasmonate	CCCCC[C@@H]1[C@@H](CC(=O)OC)CCC1=O	2378.0	Standard polar	33892256
Methyl dihydrojasmonate	CCCCC[C@@H]1[C@@H](CC(=O)OC)CCC1=O	1623.5	Standard non polar	33892256
Methyl dihydrojasmonate	CCCCC[C@@H]1[C@@H](CC(=O)OC)CCC1=O	1663.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Methyl dihydrojasmonate,1TMS,isomer #1	CCCCCC1=C(O[Si](C)(C)C)CC[C@@H]1CC(=O)OC	1781.8	Semi standard non polar	33892256
Methyl dihydrojasmonate,1TMS,isomer #1	CCCCCC1=C(O[Si](C)(C)C)CC[C@@H]1CC(=O)OC	1778.8	Standard non polar	33892256
Methyl dihydrojasmonate,1TMS,isomer #2	CCCCC[C@H]1C(O[Si](C)(C)C)=CC[C@@H]1CC(=O)OC	1763.4	Semi standard non polar	33892256
Methyl dihydrojasmonate,1TMS,isomer #2	CCCCC[C@H]1C(O[Si](C)(C)C)=CC[C@@H]1CC(=O)OC	1791.5	Standard non polar	33892256
Methyl dihydrojasmonate,1TBDMS,isomer #1	CCCCCC1=C(O[Si](C)(C)C(C)(C)C)CC[C@@H]1CC(=O)OC	2000.8	Semi standard non polar	33892256
Methyl dihydrojasmonate,1TBDMS,isomer #1	CCCCCC1=C(O[Si](C)(C)C(C)(C)C)CC[C@@H]1CC(=O)OC	1956.5	Standard non polar	33892256
Methyl dihydrojasmonate,1TBDMS,isomer #2	CCCCC[C@H]1C(O[Si](C)(C)C(C)(C)C)=CC[C@@H]1CC(=O)OC	1965.6	Semi standard non polar	33892256
Methyl dihydrojasmonate,1TBDMS,isomer #2	CCCCC[C@H]1C(O[Si](C)(C)C(C)(C)C)=CC[C@@H]1CC(=O)OC	1913.5	Standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Saliva
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	20809147	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	24421258	details

Abnormal Concentrations

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

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB008409

KNApSAcK ID

C00051556

Chemspider ID

1376701

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Methyl dihydrojasmonate

METLIN ID

Not Available

PubChem Compound

102861

PDB ID

Not Available

ChEBI ID

89741

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1015272

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for Methyl dihydrojasmonate (HMDB0031740)

MOL for HMDB0031740 (Methyl dihydrojasmonate)

3D MOL for HMDB0031740 (Methyl dihydrojasmonate)

3D SDF for HMDB0031740 (Methyl dihydrojasmonate)

3D-SDF for HMDB0031740 (Methyl dihydrojasmonate)

PDB for HMDB0031740 (Methyl dihydrojasmonate)

3D PDB for HMDB0031740 (Methyl dihydrojasmonate)

SMILES for HMDB0031740 (Methyl dihydrojasmonate)

INCHI for HMDB0031740 (Methyl dihydrojasmonate)

Structure for HMDB0031740 (Methyl dihydrojasmonate)

3D Structure for HMDB0031740 (Methyl dihydrojasmonate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized