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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:20:53 UTC

Update Date

2022-03-07 02:53:47 UTC

HMDB ID

HMDB0033601

Secondary Accession Numbers

HMDB33601

Metabolite Identification

Common Name

Dihydrojasmonic acid

Description

Dihydrojasmonic acid, also known as 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 Dihydrojasmonic acid.

Structure

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

HMDB0033601
     RDKit          3D
Dihydrojasmonic acid
 35 35  0  0  0  0  0  0  0  0999 V2000
    4.6172    0.6072   -0.9046 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1101    0.4131   -0.8252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6684    0.9090    0.5172 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1782    0.7751    0.7254 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7463   -0.6517    0.6260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7241   -0.8604    0.8257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9773   -2.3382    0.6932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1997   -3.2600    0.8513 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3953   -2.4636    0.3226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6510   -1.2737   -0.5441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5814   -0.2434   -0.2201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2860    0.9708    0.3341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1542    1.6148   -0.6866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2205    1.1286   -1.8345 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8949    2.7449   -0.3968 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9534    0.2581   -1.8992 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9109    1.6589   -0.7755 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1486   -0.0307   -0.1591 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6523    0.9680   -1.6496 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9516   -0.6816   -0.9193 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9758    1.9649    0.6290 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2114    0.3106    1.2849 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7020    1.3525   -0.1211 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9318    1.2592    1.6714 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0409   -1.0599   -0.3523 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2763   -1.2329    1.4087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0008   -0.5525    1.8310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6280   -3.4038   -0.2330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9954   -2.4003    1.2637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6689   -0.9021   -0.3272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6445   -1.5452   -1.6224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0352    0.0510   -1.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9783    0.5987    1.1345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6140    1.6973    0.7913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4257    3.6172   -0.3019 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
 11  6  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 15 35  1  0
M  END


  Mrv0541 05061307132D          

 15 15  0  0  0  0            999 V2000
    0.6725    2.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3870    3.2332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1015    2.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8159    3.2332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5304    2.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5506    3.5107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1381    4.2252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1701    2.0907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9986    2.8977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2449    3.2332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3311    4.0537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9547    1.8357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7180    4.6057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5678    2.3878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1262    1.0288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  7  6  1  0  0  0  0
  9  6  1  0  0  0  0
  9  8  1  0  0  0  0
 10  5  1  0  0  0  0
 10  9  1  0  0  0  0
 11  7  1  0  0  0  0
 11 10  1  0  0  0  0
 12  8  1  0  0  0  0
 13 11  2  0  0  0  0
 14 12  2  0  0  0  0
 15 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033601

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCC1C(CC(O)=O)CCC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H20O3/c1-2-3-4-5-10-9(8-12(14)15)6-7-11(10)13/h9-10H,2-8H2,1H3,(H,14,15)

> <INCHI_KEY>
PQEYTAGBXNEUQL-UHFFFAOYSA-N

> <FORMULA>
C12H20O3

> <MOLECULAR_WEIGHT>
212.2854

> <EXACT_MASS>
212.141244506

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
24.083800153826225

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3-oxo-2-pentylcyclopentyl)acetic acid

> <ALOGPS_LOGP>
2.67

> <JCHEM_LOGP>
2.776232534333333

> <ALOGPS_LOGS>
-2.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.766814637921793

> <JCHEM_PKA_STRONGEST_BASIC>
-7.416685251818894

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
57.43990000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.14e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3-oxo-2-pentylcyclopentyl)acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033601
     RDKit          3D
Dihydrojasmonic acid
 35 35  0  0  0  0  0  0  0  0999 V2000
    4.6172    0.6072   -0.9046 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1101    0.4131   -0.8252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6684    0.9090    0.5172 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1782    0.7751    0.7254 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7463   -0.6517    0.6260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7241   -0.8604    0.8257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9773   -2.3382    0.6932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1997   -3.2600    0.8513 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3953   -2.4636    0.3226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6510   -1.2737   -0.5441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5814   -0.2434   -0.2201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2860    0.9708    0.3341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1542    1.6148   -0.6866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2205    1.1286   -1.8345 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8949    2.7449   -0.3968 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9534    0.2581   -1.8992 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9109    1.6589   -0.7755 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1486   -0.0307   -0.1591 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6523    0.9680   -1.6496 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9516   -0.6816   -0.9193 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9758    1.9649    0.6290 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2114    0.3106    1.2849 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7020    1.3525   -0.1211 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9318    1.2592    1.6714 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0409   -1.0599   -0.3523 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2763   -1.2329    1.4087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0008   -0.5525    1.8310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6280   -3.4038   -0.2330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9954   -2.4003    1.2637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6689   -0.9021   -0.3272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6445   -1.5452   -1.6224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0352    0.0510   -1.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9783    0.5987    1.1345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6140    1.6973    0.7913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4257    3.6172   -0.3019 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
 11  6  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 15 35  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       1.255   5.265   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.589   6.035   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.923   5.265   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.256   6.035   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.590   5.265   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.361   6.553   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.591   7.887   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.651   3.903   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.331   5.409   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.924   6.035   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.085   7.567   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.115   3.427   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.940   8.597   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      12.260   4.457   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      11.436   1.920   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4   10                                                       
CONECT    6    7    9                                                       
CONECT    7    6   11                                                       
CONECT    8    9   12                                                       
CONECT    9    6    8   10                                                  
CONECT   10    5    9   11                                                  
CONECT   11    7   10   13                                                  
CONECT   12    8   14   15                                                  
CONECT   13   11                                                            
CONECT   14   12                                                            
CONECT   15   12                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0033601
HETATM    1  C1  UNL     1       4.617   0.607  -0.905  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.110   0.413  -0.825  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.668   0.909   0.517  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.178   0.775   0.725  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.746  -0.652   0.626  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.724  -0.860   0.826  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.977  -2.338   0.693  1.00  0.00           C  
HETATM    8  O1  UNL     1      -0.200  -3.260   0.851  1.00  0.00           O  
HETATM    9  C8  UNL     1      -2.395  -2.464   0.323  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.651  -1.274  -0.544  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.581  -0.243  -0.220  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.286   0.971   0.334  1.00  0.00           C  
HETATM   13  C12 UNL     1      -3.154   1.615  -0.687  1.00  0.00           C  
HETATM   14  O2  UNL     1      -3.220   1.129  -1.834  1.00  0.00           O  
HETATM   15  O3  UNL     1      -3.895   2.745  -0.397  1.00  0.00           O  
HETATM   16  H1  UNL     1       4.953   0.258  -1.899  1.00  0.00           H  
HETATM   17  H2  UNL     1       4.911   1.659  -0.775  1.00  0.00           H  
HETATM   18  H3  UNL     1       5.149  -0.031  -0.159  1.00  0.00           H  
HETATM   19  H4  UNL     1       2.652   0.968  -1.650  1.00  0.00           H  
HETATM   20  H5  UNL     1       2.952  -0.682  -0.919  1.00  0.00           H  
HETATM   21  H6  UNL     1       2.976   1.965   0.629  1.00  0.00           H  
HETATM   22  H7  UNL     1       3.211   0.311   1.285  1.00  0.00           H  
HETATM   23  H8  UNL     1       0.702   1.352  -0.121  1.00  0.00           H  
HETATM   24  H9  UNL     1       0.932   1.259   1.671  1.00  0.00           H  
HETATM   25  H10 UNL     1       1.041  -1.060  -0.352  1.00  0.00           H  
HETATM   26  H11 UNL     1       1.276  -1.233   1.409  1.00  0.00           H  
HETATM   27  H12 UNL     1      -1.001  -0.552   1.831  1.00  0.00           H  
HETATM   28  H13 UNL     1      -2.628  -3.404  -0.233  1.00  0.00           H  
HETATM   29  H14 UNL     1      -2.995  -2.400   1.264  1.00  0.00           H  
HETATM   30  H15 UNL     1      -3.669  -0.902  -0.327  1.00  0.00           H  
HETATM   31  H16 UNL     1      -2.645  -1.545  -1.622  1.00  0.00           H  
HETATM   32  H17 UNL     1      -1.035   0.051  -1.137  1.00  0.00           H  
HETATM   33  H18 UNL     1      -2.978   0.599   1.134  1.00  0.00           H  
HETATM   34  H19 UNL     1      -1.614   1.697   0.791  1.00  0.00           H  
HETATM   35  H20 UNL     1      -3.426   3.617  -0.302  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3   19   20
CONECT    3    4   21   22
CONECT    4    5   23   24
CONECT    5    6   25   26
CONECT    6    7   11   27
CONECT    7    8    8    9
CONECT    9   10   28   29
CONECT   10   11   30   31
CONECT   11   12   32
CONECT   12   13   33   34
CONECT   13   14   14   15
CONECT   15   35
END

HMDB0033601
     RDKit          3D
Dihydrojasmonic acid
 35 35  0  0  0  0  0  0  0  0999 V2000
    4.6172    0.6072   -0.9046 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1101    0.4131   -0.8252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6684    0.9090    0.5172 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1782    0.7751    0.7254 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7463   -0.6517    0.6260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7241   -0.8604    0.8257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9773   -2.3382    0.6932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1997   -3.2600    0.8513 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3953   -2.4636    0.3226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6510   -1.2737   -0.5441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5814   -0.2434   -0.2201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2860    0.9708    0.3341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1542    1.6148   -0.6866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2205    1.1286   -1.8345 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8949    2.7449   -0.3968 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9534    0.2581   -1.8992 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9109    1.6589   -0.7755 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1486   -0.0307   -0.1591 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6523    0.9680   -1.6496 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9516   -0.6816   -0.9193 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9758    1.9649    0.6290 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2114    0.3106    1.2849 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7020    1.3525   -0.1211 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9318    1.2592    1.6714 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0409   -1.0599   -0.3523 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2763   -1.2329    1.4087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0008   -0.5525    1.8310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6280   -3.4038   -0.2330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9954   -2.4003    1.2637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6689   -0.9021   -0.3272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6445   -1.5452   -1.6224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0352    0.0510   -1.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9783    0.5987    1.1345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6140    1.6973    0.7913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4257    3.6172   -0.3019 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
 11  6  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 15 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Dihydrojasmonate	Generator
(-)-9,10-Dihydrojasmonic acid	HMDB
(-)-Dihydrojasmonic acid	HMDB
2-[(1R,2R)-3-oxo-2-Pentylcyclopentyl]acetic acid	HMDB
3-oxo-2-Pentyl-(1R-trans)-cyclopentaneacetic acid	HMDB
9,10-Dihydrojasmonic acid	HMDB
Cyclopentaneacetic acid, 3-oxo-2-pentyl-, (1R,2R)- (9ci)	HMDB
[(1R,2R)-3-oxo-2-Pentylcyclopentyl]acetic acid	HMDB
2-(3-oxo-2-Pentylcyclopentyl)acetate	Generator

Chemical Formula

C₁₂H₂₀O₃

Average Molecular Weight

212.2854

Monoisotopic Molecular Weight

212.141244506

IUPAC Name

2-(3-oxo-2-pentylcyclopentyl)acetic acid

Traditional Name

(3-oxo-2-pentylcyclopentyl)acetic acid

CAS Registry Number

98674-52-3

SMILES

CCCCCC1C(CC(O)=O)CCC1=O

InChI Identifier

InChI=1S/C12H20O3/c1-2-3-4-5-10-9(8-12(14)15)6-7-11(10)13/h9-10H,2-8H2,1H3,(H,14,15)

InChI Key

PQEYTAGBXNEUQL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as jasmonic acids. These are lipids containing or derived from a jasmonic acid, with a structure characterized by the presence of an alkene chain linked to a 2-(3-oxocyclopentyl)acetic acid moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Lineolic acids and derivatives

Direct Parent

Jasmonic acids

Alternative Parents

Substituents

Jasmonic acid
Cyclic ketone
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0033601)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033601)

Source

Endogenous

Endogenous (HMDB: HMDB0033601)

Plant

Poaceae (HMDB: HMDB0033601)
Fabaceae (HMDB: HMDB0033601)

Animal

Animal (HMDB: HMDB0033601)

Exogenous

Food

Food (HMDB: HMDB0033601)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereal

Rye (FooDB: FOOD00169)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Bean

Broad bean (FooDB: FOOD00197)

Pulses (FooDB: FOOD00867)

Exogenous (HMDB: HMDB0033601)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0033601)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0033601)

Lipid metabolism pathway (HMDB: HMDB0033601)

Cellular process

Cell signaling (HMDB: HMDB0033601)

Biochemical process

Lipid transport (HMDB: HMDB0033601)

Role

Biological role

Energy source (HMDB: HMDB0033601)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0033601)

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

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	147.027	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001216

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.51 g/L	ALOGPS
logP	2.67	ALOGPS
logP	2.78	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	4.77	ChemAxon
pKa (Strongest Basic)	-7.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	57.44 m³·mol⁻¹	ChemAxon
Polarizability	24.08 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]+	150.784	31661259
DarkChem	[M-H]-	146.595	31661259
DeepCCS	[M+H]+	154.602	30932474
DeepCCS	[M-H]-	150.582	30932474
DeepCCS	[M-2H]-	188.074	30932474
DeepCCS	[M+Na]+	163.738	30932474
AllCCS	[M+H]+	151.0	32859911
AllCCS	[M+H-H2O]+	147.3	32859911
AllCCS	[M+NH4]+	154.5	32859911
AllCCS	[M+Na]+	155.5	32859911
AllCCS	[M-H]-	154.3	32859911
AllCCS	[M+Na-2H]-	155.1	32859911
AllCCS	[M+HCOO]-	156.1	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.	5.45 minutes	32390414
Predicted by Siyang on May 30, 2022	13.3928 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.01 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2193.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	359.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	163.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	195.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	337.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	568.6 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	556.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	78.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1173.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	416.1 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	1330.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	312.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	369.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	322.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	270.9 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	73.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dihydrojasmonic acid	CCCCCC1C(CC(O)=O)CCC1=O	3069.9	Standard polar	33892256
Dihydrojasmonic acid	CCCCCC1C(CC(O)=O)CCC1=O	1642.8	Standard non polar	33892256
Dihydrojasmonic acid	CCCCCC1C(CC(O)=O)CCC1=O	1732.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dihydrojasmonic acid,1TMS,isomer #1	CCCCCC1C(=O)CCC1CC(=O)O[Si](C)(C)C	1752.4	Semi standard non polar	33892256
Dihydrojasmonic acid,1TMS,isomer #2	CCCCCC1=C(O[Si](C)(C)C)CCC1CC(=O)O	1861.3	Semi standard non polar	33892256
Dihydrojasmonic acid,1TMS,isomer #3	CCCCCC1C(O[Si](C)(C)C)=CCC1CC(=O)O	1851.5	Semi standard non polar	33892256
Dihydrojasmonic acid,2TMS,isomer #1	CCCCCC1=C(O[Si](C)(C)C)CCC1CC(=O)O[Si](C)(C)C	1890.4	Semi standard non polar	33892256
Dihydrojasmonic acid,2TMS,isomer #1	CCCCCC1=C(O[Si](C)(C)C)CCC1CC(=O)O[Si](C)(C)C	1895.2	Standard non polar	33892256
Dihydrojasmonic acid,2TMS,isomer #2	CCCCCC1C(O[Si](C)(C)C)=CCC1CC(=O)O[Si](C)(C)C	1866.9	Semi standard non polar	33892256
Dihydrojasmonic acid,2TMS,isomer #2	CCCCCC1C(O[Si](C)(C)C)=CCC1CC(=O)O[Si](C)(C)C	1965.3	Standard non polar	33892256
Dihydrojasmonic acid,1TBDMS,isomer #1	CCCCCC1C(=O)CCC1CC(=O)O[Si](C)(C)C(C)(C)C	2001.0	Semi standard non polar	33892256
Dihydrojasmonic acid,1TBDMS,isomer #2	CCCCCC1=C(O[Si](C)(C)C(C)(C)C)CCC1CC(=O)O	2097.1	Semi standard non polar	33892256
Dihydrojasmonic acid,1TBDMS,isomer #3	CCCCCC1C(O[Si](C)(C)C(C)(C)C)=CCC1CC(=O)O	2110.3	Semi standard non polar	33892256
Dihydrojasmonic acid,2TBDMS,isomer #1	CCCCCC1=C(O[Si](C)(C)C(C)(C)C)CCC1CC(=O)O[Si](C)(C)C(C)(C)C	2356.7	Semi standard non polar	33892256
Dihydrojasmonic acid,2TBDMS,isomer #1	CCCCCC1=C(O[Si](C)(C)C(C)(C)C)CCC1CC(=O)O[Si](C)(C)C(C)(C)C	2261.6	Standard non polar	33892256
Dihydrojasmonic acid,2TBDMS,isomer #2	CCCCCC1C(O[Si](C)(C)C(C)(C)C)=CCC1CC(=O)O[Si](C)(C)C(C)(C)C	2336.8	Semi standard non polar	33892256
Dihydrojasmonic acid,2TBDMS,isomer #2	CCCCCC1C(O[Si](C)(C)C(C)(C)C)=CCC1CC(=O)O[Si](C)(C)C(C)(C)C	2220.8	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrojasmonic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a59-9600000000-a963304d4e038fcd9c1b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrojasmonic acid GC-MS (1 TMS) - 70eV, Positive	splash10-0609-9330000000-5ce665ebe4299971835c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrojasmonic acid 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 - Dihydrojasmonic acid Linear Ion Trap , negative-QTOF	splash10-0uxr-0900000000-b303cae9ee8e5d7bd0da	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dihydrojasmonic acid Linear Ion Trap , negative-QTOF	splash10-0uxr-0900000000-914f9c7a0975ead91646	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dihydrojasmonic acid Linear Ion Trap , positive-QTOF	splash10-00di-0910000000-a2ea5ad50a81fdc7d4db	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dihydrojasmonic acid Linear Ion Trap , positive-QTOF	splash10-00di-0910000000-e33f64ee8b0ce2d8accb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dihydrojasmonic acid Linear Ion Trap , positive-QTOF	splash10-05fs-1920000000-1f46edcb69535fd6f256	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dihydrojasmonic acid Linear Ion Trap , positive-QTOF	splash10-05fs-1920000000-b530d5c2d414d7916042	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrojasmonic acid 10V, Positive-QTOF	splash10-03dj-1940000000-5d011658ee98c357edb8	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrojasmonic acid 20V, Positive-QTOF	splash10-067i-9800000000-d3f3210ced953edfb6d4	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrojasmonic acid 40V, Positive-QTOF	splash10-0536-9100000000-0b0112539d956b87844d	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrojasmonic acid 10V, Negative-QTOF	splash10-03xr-0690000000-dc3c55ff0fb30649e35d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrojasmonic acid 20V, Negative-QTOF	splash10-03xr-2950000000-dd87add970fc731fde5a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrojasmonic acid 40V, Negative-QTOF	splash10-0a4l-9400000000-f10c1bc6eebbf980f38f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrojasmonic acid 10V, Negative-QTOF	splash10-0a4i-9030000000-cfb8da3c820cc54d289b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrojasmonic acid 20V, Negative-QTOF	splash10-0a4i-9010000000-3f9321826bd41457eaf5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrojasmonic acid 40V, Negative-QTOF	splash10-0006-9300000000-f55beeb2372735360ed4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrojasmonic acid 10V, Positive-QTOF	splash10-01r2-3920000000-d1ed5586cd10e74a6ad7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrojasmonic acid 20V, Positive-QTOF	splash10-01ow-7910000000-ac1c943f0451806690cb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrojasmonic acid 40V, Positive-QTOF	splash10-053u-9000000000-162f85e6038957a18c05	2021-09-22	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

FDB011689

KNApSAcK ID

C00000225

Chemspider ID

96397

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

107126

PDB ID

Not Available

ChEBI ID

Not Available

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

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 Dihydrojasmonic acid (HMDB0033601)

MOL for HMDB0033601 (Dihydrojasmonic acid)

3D MOL for HMDB0033601 (Dihydrojasmonic acid)

3D SDF for HMDB0033601 (Dihydrojasmonic acid)

3D-SDF for HMDB0033601 (Dihydrojasmonic acid)

PDB for HMDB0033601 (Dihydrojasmonic acid)

3D PDB for HMDB0033601 (Dihydrojasmonic acid)

SMILES for HMDB0033601 (Dihydrojasmonic acid)

INCHI for HMDB0033601 (Dihydrojasmonic acid)

Structure for HMDB0033601 (Dihydrojasmonic acid)

3D Structure for HMDB0033601 (Dihydrojasmonic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra