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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 05:49:38 UTC

Update Date

2021-09-24 05:49:39 UTC

HMDB ID

HMDB0303939

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(+)-7-iso-jasmonate

Description

(+)-7-iso-jasmonate is a member of the class of compounds known as jasmonic acids. Jasmonic acids 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 (+)-7-iso-jasmonate is practically insoluble (in water) and a weakly acidic compound (based on its pKa). (+)-7-iso-jasmonate can be found in a number of food items such as tarragon, celery leaves, sweet marjoram, and rape, which makes (+)-7-iso-jasmonate a potential biomarker for the consumption of these food products.

Structure

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

HMDB0303939
     RDKit          3D
(+)-7-iso-jasmonate
 32 32  0  0  0  0  0  0  0  0999 V2000
    4.4311    0.4728    1.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8931    0.2647   -0.2228 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6944   -0.6111   -0.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4926   -0.2239   -0.5203 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3687   -1.1537   -0.3770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7420   -0.6344    0.4916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7976   -1.7009    0.5283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0437   -2.4900    1.4104 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5009   -1.5909   -0.7738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6084   -0.0903   -0.9416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4983    0.5101   -0.1302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1223    1.3149    0.9848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8946    2.4766    0.4312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9348    2.6417   -0.8183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5471    3.3469    1.2630 O   0  0  0  0  0  1  0  0  0  0  0  0
    4.9787   -0.4768    1.4367 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5776    0.5201    1.8768 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1108    1.3284    1.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6746   -0.2728   -0.8099 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6412    1.2130   -0.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8731   -1.6044    0.3204 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4114    0.7697   -0.9374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0411   -1.3507   -1.3886 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7000   -2.1166    0.0504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4351   -0.3793    1.5011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4990   -2.0774   -0.7415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9452   -2.0504   -1.6112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6200    0.2052   -0.5761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5347    0.1656   -2.0239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8691    1.1671   -0.7451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8273    0.7007    1.5816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3862    1.7260    1.6918 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  3
  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
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
M  CHG  1  15  -1
M  END


  Mrv1533004251517022D          

 15 15  0  0  0  0            999 V2000
   -0.8612    4.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    3.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0198    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6329    0.3323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4175    0.5872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4614   -0.4747    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  4  0  0  0
  3  4  2  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
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  2  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
M  CHG  1  15  -1
M  END
> <DATABASE_ID>
HMDB0303939

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC=CCC1C(CC([O-])=O)CCC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H18O3/c1-2-3-4-5-10-9(8-12(14)15)6-7-11(10)13/h3-4,9-10H,2,5-8H2,1H3,(H,14,15)/p-1

> <INCHI_KEY>
ZNJFBWYDHIGLCU-UHFFFAOYSA-M

> <FORMULA>
C12H17O3

> <MOLECULAR_WEIGHT>
209.266

> <EXACT_MASS>
209.118317987

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
22.80475207024753

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.49

> <JCHEM_LOGP>
2.4143108776666664

> <ALOGPS_LOGS>
-2.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.714081549780867

> <JCHEM_PKA_STRONGEST_BASIC>
-7.4223839862661904

> <JCHEM_POLAR_SURFACE_AREA>
57.2

> <JCHEM_REFRACTIVITY>
69.3936

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.23e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[3-oxo-2-(pent-2-en-1-yl)cyclopentyl]acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0303939
     RDKit          3D
(+)-7-iso-jasmonate
 32 32  0  0  0  0  0  0  0  0999 V2000
    4.4311    0.4728    1.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8931    0.2647   -0.2228 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6944   -0.6111   -0.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4926   -0.2239   -0.5203 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3687   -1.1537   -0.3770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7420   -0.6344    0.4916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7976   -1.7009    0.5283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0437   -2.4900    1.4104 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5009   -1.5909   -0.7738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6084   -0.0903   -0.9416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4983    0.5101   -0.1302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1223    1.3149    0.9848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8946    2.4766    0.4312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9348    2.6417   -0.8183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5471    3.3469    1.2630 O   0  0  0  0  0  1  0  0  0  0  0  0
    4.9787   -0.4768    1.4367 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5776    0.5201    1.8768 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1108    1.3284    1.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6746   -0.2728   -0.8099 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6412    1.2130   -0.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8731   -1.6044    0.3204 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4114    0.7697   -0.9374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0411   -1.3507   -1.3886 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7000   -2.1166    0.0504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4351   -0.3793    1.5011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4990   -2.0774   -0.7415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9452   -2.0504   -1.6112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6200    0.2052   -0.5761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5347    0.1656   -2.0239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8691    1.1671   -0.7451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8273    0.7007    1.5816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3862    1.7260    1.6918 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  3
  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
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
M  CHG  1  15  -1
M  END

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      -1.608   8.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.608   6.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.274   5.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.274   4.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.651   1.651   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.770   1.651   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.915   0.620   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.379   1.096   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       4.595  -0.886   0.000  0.00  0.00           O-1
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    6   11                                                  
CONECT   11   10                                                            
CONECT   12    7   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0303939
HETATM    1  C1  UNL     1       4.431   0.473   1.169  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.893   0.265  -0.223  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.694  -0.611  -0.117  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.493  -0.224  -0.520  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.369  -1.154  -0.377  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.742  -0.634   0.492  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.798  -1.701   0.528  1.00  0.00           C  
HETATM    8  O1  UNL     1      -2.044  -2.490   1.410  1.00  0.00           O  
HETATM    9  C8  UNL     1      -2.501  -1.591  -0.774  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.608  -0.090  -0.942  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.498   0.510  -0.130  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.122   1.315   0.985  1.00  0.00           C  
HETATM   13  C12 UNL     1      -2.895   2.477   0.431  1.00  0.00           C  
HETATM   14  O2  UNL     1      -2.935   2.642  -0.818  1.00  0.00           O  
HETATM   15  O3  UNL     1      -3.547   3.347   1.263  1.00  0.00           O1-
HETATM   16  H1  UNL     1       4.979  -0.477   1.437  1.00  0.00           H  
HETATM   17  H2  UNL     1       3.578   0.520   1.877  1.00  0.00           H  
HETATM   18  H3  UNL     1       5.111   1.328   1.247  1.00  0.00           H  
HETATM   19  H4  UNL     1       4.675  -0.273  -0.810  1.00  0.00           H  
HETATM   20  H5  UNL     1       3.641   1.213  -0.734  1.00  0.00           H  
HETATM   21  H6  UNL     1       2.873  -1.604   0.320  1.00  0.00           H  
HETATM   22  H7  UNL     1       1.411   0.770  -0.937  1.00  0.00           H  
HETATM   23  H8  UNL     1      -0.041  -1.351  -1.389  1.00  0.00           H  
HETATM   24  H9  UNL     1       0.700  -2.117   0.050  1.00  0.00           H  
HETATM   25  H10 UNL     1      -0.435  -0.379   1.501  1.00  0.00           H  
HETATM   26  H11 UNL     1      -3.499  -2.077  -0.742  1.00  0.00           H  
HETATM   27  H12 UNL     1      -1.945  -2.050  -1.611  1.00  0.00           H  
HETATM   28  H13 UNL     1      -3.620   0.205  -0.576  1.00  0.00           H  
HETATM   29  H14 UNL     1      -2.535   0.166  -2.024  1.00  0.00           H  
HETATM   30  H15 UNL     1      -0.869   1.167  -0.745  1.00  0.00           H  
HETATM   31  H16 UNL     1      -2.827   0.701   1.582  1.00  0.00           H  
HETATM   32  H17 UNL     1      -1.386   1.726   1.692  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3   19   20
CONECT    3    4    4   21
CONECT    4    5   22
CONECT    5    6   23   24
CONECT    6    7   11   25
CONECT    7    8    8    9
CONECT    9   10   26   27
CONECT   10   11   28   29
CONECT   11   12   30
CONECT   12   13   31   32
CONECT   13   14   14   15
END

HMDB0303939
     RDKit          3D
(+)-7-iso-jasmonate
 32 32  0  0  0  0  0  0  0  0999 V2000
    4.4311    0.4728    1.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8931    0.2647   -0.2228 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6944   -0.6111   -0.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4926   -0.2239   -0.5203 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3687   -1.1537   -0.3770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7420   -0.6344    0.4916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7976   -1.7009    0.5283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0437   -2.4900    1.4104 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5009   -1.5909   -0.7738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6084   -0.0903   -0.9416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4983    0.5101   -0.1302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1223    1.3149    0.9848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8946    2.4766    0.4312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9348    2.6417   -0.8183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5471    3.3469    1.2630 O   0  0  0  0  0  1  0  0  0  0  0  0
    4.9787   -0.4768    1.4367 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5776    0.5201    1.8768 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1108    1.3284    1.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6746   -0.2728   -0.8099 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6412    1.2130   -0.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8731   -1.6044    0.3204 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4114    0.7697   -0.9374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0411   -1.3507   -1.3886 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7000   -2.1166    0.0504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4351   -0.3793    1.5011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4990   -2.0774   -0.7415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9452   -2.0504   -1.6112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6200    0.2052   -0.5761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5347    0.1656   -2.0239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8691    1.1671   -0.7451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8273    0.7007    1.5816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3862    1.7260    1.6918 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  3
  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
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
M  CHG  1  15  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-[3-oxo-2-(Pent-2-en-1-yl)cyclopentyl]acetic acid	Generator
(+)-7-Iso-jasmonic acid	Generator

Chemical Formula

C₁₂H₁₇O₃

Average Molecular Weight

209.266

Monoisotopic Molecular Weight

209.118317987

IUPAC Name

2-[3-oxo-2-(pent-2-en-1-yl)cyclopentyl]acetate

Traditional Name

2-[3-oxo-2-(pent-2-en-1-yl)cyclopentyl]acetate

CAS Registry Number

Not Available

SMILES

CCC=CCC1C(CC([O-])=O)CCC1=O

InChI Identifier

InChI=1S/C12H18O3/c1-2-3-4-5-10-9(8-12(14)15)6-7-11(10)13/h3-4,9-10H,2,5-8H2,1H3,(H,14,15)/p-1

InChI Key

ZNJFBWYDHIGLCU-UHFFFAOYSA-M

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
Organic anion
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

a jasmonic acid (CPD-734 )

Ontology

Not Available

Herbs and Spices (FooDB: FOOD00866)

Nut

Almond (FooDB: FOOD00148)
Brazil nut (FooDB: FOOD00024)
Cashew nut (FooDB: FOOD00011)
Chestnut (FooDB: FOOD00045)
Hazelnut (FooDB: FOOD00376)
Peanut (FooDB: FOOD00016)
Pecan nut (FooDB: FOOD00044)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Walnut (FooDB: FOOD00608)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hickory nut (FooDB: FOOD00377)
Macadamia nut (FooDB: FOOD00525)
Mixed nuts (FooDB: FOOD00771)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Japanese chestnut (FooDB: FOOD00385)
Common hazelnut (FooDB: FOOD00062)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Nuts (FooDB: FOOD00869)

Fruit

Pome

Drupe

Apricot (FooDB: FOOD00144)
Prunus (Cherry, Plum) (FooDB: FOOD00143)
Nectarine (FooDB: FOOD00229)
Peach (FooDB: FOOD00149)
European plum (FooDB: FOOD00147)
Sour cherry (FooDB: FOOD00146)
Sweet cherry (FooDB: FOOD00145)
Common chokecherry (FooDB: FOOD00562)
Peach (var.) (FooDB: FOOD00230)

Tropical fruit

Berry

Bilberry (FooDB: FOOD00193)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Elderberry (FooDB: FOOD00358)
Gooseberry (FooDB: FOOD00157)
Grape (FooDB: FOOD00369)
Lingonberry (FooDB: FOOD00194)
Loganberry (FooDB: FOOD00400)
Strawberry (FooDB: FOOD00083)
Boysenberry (FooDB: FOOD00542)
American cranberry (FooDB: FOOD00192)
Common grape (FooDB: FOOD00204)
Strawberry guava (FooDB: FOOD00482)
Black mulberry (FooDB: FOOD00117)
Red raspberry (FooDB: FOOD00162)
Muscadine grape (FooDB: FOOD00203)
Salmonberry (FooDB: FOOD00456)
Alaska blueberry (FooDB: FOOD00380)
Sea-buckthornberry (FooDB: FOOD00087)
Black elderberry (FooDB: FOOD00166)
Black crowberry (FooDB: FOOD00075)
Black huckleberry (FooDB: FOOD00084)
Mulberry (FooDB: FOOD00116)
Black chokeberry (FooDB: FOOD00136)
Cloudberry (FooDB: FOOD00161)
Black raspberry (FooDB: FOOD00163)
Rowanberry (FooDB: FOOD00176)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Ohelo berry (FooDB: FOOD00419)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)

Other fruit

Date (FooDB: FOOD00135)
Fig (FooDB: FOOD00081)
Jujube (FooDB: FOOD00388)

Citrus

Grapefruit (FooDB: FOOD00256)
Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Persian lime (FooDB: FOOD00543)
Pummelo (FooDB: FOOD00055)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Citrus (FooDB: FOOD00859)

Fruits (FooDB: FOOD00871)

Vegetable

Shoot vegetable

Fruit vegetable

Eggplant (FooDB: FOOD00174)
Avocado (FooDB: FOOD00130)
Groundcherry (FooDB: FOOD00371)
Olive (FooDB: FOOD00121)
Pepper (FooDB: FOOD00040)
Garden tomato (FooDB: FOOD00171)
Mexican groundcherry (FooDB: FOOD00491)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Garden tomato (var.) (FooDB: FOOD00173)
Cherry tomato (FooDB: FOOD00172)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Pepper (C. frutescens) (FooDB: FOOD00428)
Pepper (C. pubescens) (FooDB: FOOD00849)
Orange bell pepper (FooDB: FOOD00879)

Root vegetable

Cabbage

Leaf vegetable

Lettuce (FooDB: FOOD00095)
Swiss chard (FooDB: FOOD00237)
Garden cress (FooDB: FOOD00099)
Endive (FooDB: FOOD00048)
Spinach (FooDB: FOOD00178)
Common beet (FooDB: FOOD00025)
Garland chrysanthemum (FooDB: FOOD00333)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
New Zealand spinach (FooDB: FOOD00415)
Swamp cabbage (FooDB: FOOD00091)
Rocket salad (ssp.) (FooDB: FOOD00077)
Yautia (FooDB: FOOD00510)
Romaine lettuce (FooDB: FOOD00888)
Rocket salad (FooDB: FOOD00244)
Chicory leaves (FooDB: FOOD00250)
Corn salad (FooDB: FOOD00340)
Malabar spinach (FooDB: FOOD00404)
Ostrich fern (FooDB: FOOD00556)
Green vegetables (FooDB: FOOD00872)

Mushroom

Tuber

Onion-family vegetable

Leek (FooDB: FOOD00007)
Allium (FooDB: FOOD00005)
Wild leek (FooDB: FOOD00396)
Shallot (FooDB: FOOD00243)
Garden onion (FooDB: FOOD00006)
Garden onion (var.) (FooDB: FOOD00226)
Onion-family vegetables (FooDB: FOOD00855)
Green onion (FooDB: FOOD00963)
Red onion (FooDB: FOOD00962)

Other vegetable

Okra (FooDB: FOOD00420)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Tree fern (FooDB: FOOD00797)
Chinese water chestnut (FooDB: FOOD00332)
Nopal (FooDB: FOOD00416)
Carob (FooDB: FOOD00321)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Giant butterbur (FooDB: FOOD00314)
Sesbania flower (FooDB: FOOD00469)

Stalk vegetable

Brassica

Brassicas (FooDB: FOOD00857)

Cereal and cereal product

Other bread

Other bread (FooDB: FOOD00269)

Cereal

Cereal product

Dough

Sourdough (FooDB: FOOD00275)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Bean

Lentil

Lentils (FooDB: FOOD00098)

Pea

Other pulse

White lupine (FooDB: FOOD00403)
Lupine (FooDB: FOOD00104)

Pulses (FooDB: FOOD00867)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Other soy product (FooDB: FOOD00271)

Abalone (FooDB: FOOD00279)
Conch (FooDB: FOOD00611)

Gourd

Chayote (FooDB: FOOD00325)
Cucumber (FooDB: FOOD00065)
Muskmelon (FooDB: FOOD00064)
Cucurbita (FooDB: FOOD00066)
Watermelon (FooDB: FOOD00052)
Bitter gourd (FooDB: FOOD00115)
Calabash (FooDB: FOOD00318)
Towel gourd (FooDB: FOOD00492)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Wax gourd (FooDB: FOOD00499)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)

Tea

Herbal tea

Greenthread tea (FooDB: FOOD00820)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.49	ALOGPS
logP	2.41	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	4.71	ChemAxon
pKa (Strongest Basic)	-7.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	57.2 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	69.39 m³·mol⁻¹	ChemAxon
Polarizability	22.8 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	149.65	32859911
AllCCS	[M+H-H2O]+	145.776	32859911
AllCCS	[M+Na]+	154.289	32859911
AllCCS	[M+NH4]+	153.252	32859911
AllCCS	[M-H]-	150.751	32859911
AllCCS	[M+Na-2H]-	151.378	32859911
AllCCS	[M+HCOO]-	152.166	32859911
DeepCCS	[M+H]+	145.352	30932474
DeepCCS	[M-H]-	142.525	30932474
DeepCCS	[M-2H]-	178.762	30932474
DeepCCS	[M+Na]+	154.302	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(+)-7-iso-jasmonate,1TMS,isomer #1	CCC=CCC1=C(O[Si](C)(C)C)CCC1CC(=O)[O-]	1735.9	Semi standard non polar	33892256
(+)-7-iso-jasmonate,1TMS,isomer #1	CCC=CCC1=C(O[Si](C)(C)C)CCC1CC(=O)[O-]	1725.6	Standard non polar	33892256
(+)-7-iso-jasmonate,1TMS,isomer #1	CCC=CCC1=C(O[Si](C)(C)C)CCC1CC(=O)[O-]	2100.5	Standard polar	33892256
(+)-7-iso-jasmonate,1TMS,isomer #2	CCC=CCC1C(O[Si](C)(C)C)=CCC1CC(=O)[O-]	1732.0	Semi standard non polar	33892256
(+)-7-iso-jasmonate,1TMS,isomer #2	CCC=CCC1C(O[Si](C)(C)C)=CCC1CC(=O)[O-]	1746.7	Standard non polar	33892256
(+)-7-iso-jasmonate,1TMS,isomer #2	CCC=CCC1C(O[Si](C)(C)C)=CCC1CC(=O)[O-]	2122.2	Standard polar	33892256
(+)-7-iso-jasmonate,1TBDMS,isomer #1	CCC=CCC1=C(O[Si](C)(C)C(C)(C)C)CCC1CC(=O)[O-]	1989.3	Semi standard non polar	33892256
(+)-7-iso-jasmonate,1TBDMS,isomer #1	CCC=CCC1=C(O[Si](C)(C)C(C)(C)C)CCC1CC(=O)[O-]	1916.6	Standard non polar	33892256
(+)-7-iso-jasmonate,1TBDMS,isomer #1	CCC=CCC1=C(O[Si](C)(C)C(C)(C)C)CCC1CC(=O)[O-]	2225.2	Standard polar	33892256
(+)-7-iso-jasmonate,1TBDMS,isomer #2	CCC=CCC1C(O[Si](C)(C)C(C)(C)C)=CCC1CC(=O)[O-]	1988.7	Semi standard non polar	33892256
(+)-7-iso-jasmonate,1TBDMS,isomer #2	CCC=CCC1C(O[Si](C)(C)C(C)(C)C)=CCC1CC(=O)[O-]	1895.4	Standard non polar	33892256
(+)-7-iso-jasmonate,1TBDMS,isomer #2	CCC=CCC1C(O[Si](C)(C)C(C)(C)C)=CCC1CC(=O)[O-]	2229.3	Standard polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-7-iso-jasmonate 10V, Negative-QTOF	splash10-066r-0950000000-4b41e15ab3399090b769	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-7-iso-jasmonate 20V, Negative-QTOF	splash10-014i-0920000000-ccb329029603a32c9a03	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-7-iso-jasmonate 40V, Negative-QTOF	splash10-0005-7900000000-0b20520e892ca566745c	2019-02-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB030077

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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

Not Available

Showing metabocard for (+)-7-iso-jasmonate (HMDB0303939)

MOL for HMDB0303939 ((+)-7-iso-jasmonate)

3D MOL for HMDB0303939 ((+)-7-iso-jasmonate)

3D SDF for HMDB0303939 ((+)-7-iso-jasmonate)

3D-SDF for HMDB0303939 ((+)-7-iso-jasmonate)

PDB for HMDB0303939 ((+)-7-iso-jasmonate)

3D PDB for HMDB0303939 ((+)-7-iso-jasmonate)

SMILES for HMDB0303939 ((+)-7-iso-jasmonate)

INCHI for HMDB0303939 ((+)-7-iso-jasmonate)

Structure for HMDB0303939 ((+)-7-iso-jasmonate)

3D Structure for HMDB0303939 ((+)-7-iso-jasmonate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra