Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:35:24 UTC

Update Date

2023-02-21 17:19:30 UTC

HMDB ID

HMDB0030197

Secondary Accession Numbers

HMDB30197

Metabolite Identification

Common Name

(Z)-3-Oxo-2-(2-pentenyl)-1-cyclopenteneacetic acid

Description

(Z)-3-Oxo-2-(2-pentenyl)-1-cyclopenteneacetic acid, also known as 2-{3-oxo-2-[(2E)-pent-2-en-1-yl]cyclopent-1-en-1-yl}acetate, belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety. Based on a literature review very few articles have been published on (Z)-3-Oxo-2-(2-pentenyl)-1-cyclopenteneacetic acid.

Structure

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

HMDB0030197
     RDKit          3D
(Z)-3-Oxo-2-(2-pentenyl)-1-cyclopenteneacetic acid
 31 31  0  0  0  0  0  0  0  0999 V2000
    4.3018    0.5686    0.0731 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7292   -0.6411   -0.6614 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3338   -0.3871   -1.1042 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3454   -1.1673   -0.6670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0628   -0.9611   -1.0747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9112   -0.6968    0.1149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6337    0.3773    0.3798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7504    1.5886   -0.4904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1929    1.7186   -0.8393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0482    2.1351   -0.0487 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5781    1.3468   -2.1279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3316    0.1940    1.7023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5333   -0.8816    2.3915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0623   -1.6673    1.2222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8150   -2.8896    1.0932 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3944    0.4577    0.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9122    0.6513    1.0953 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0175    1.4698   -0.4884 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7480   -1.4876    0.0448 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3738   -0.8754   -1.5136 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0864    0.4112   -1.7722 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5639   -1.9850    0.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3908   -1.9615   -1.4922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1851   -0.2156   -1.8599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1255    1.4892   -1.3808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4802    2.4840    0.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2184    1.9827   -2.5959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3675    1.1476    2.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3506   -0.2320    1.5179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1496   -1.4905    3.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6190   -0.4831    2.8982 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  7 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14  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
  8 25  1  0
  8 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 13 31  1  0
M  END


  Mrv0541 05061305042D          

 15 15  0  0  0  0            999 V2000
   -0.0012    3.6023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6143    3.0503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4427    2.2433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0558    1.6913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    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
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    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
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1501   -0.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6351   -1.4039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4857    0.0172    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  2  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  2  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>
HMDB0030197

> <DATABASE_NAME>
hmdb

> <SMILES>
CC\C=C\CC1=C(CC(O)=O)CCC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H16O3/c1-2-3-4-5-10-9(8-12(14)15)6-7-11(10)13/h3-4H,2,5-8H2,1H3,(H,14,15)/b4-3+

> <INCHI_KEY>
QAAHGFINENUHAR-ONEGZZNKSA-N

> <FORMULA>
C12H16O3

> <MOLECULAR_WEIGHT>
208.2536

> <EXACT_MASS>
208.109944378

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
22.78179277839979

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-{3-oxo-2-[(2E)-pent-2-en-1-yl]cyclopent-1-en-1-yl}acetic acid

> <ALOGPS_LOGP>
2.30

> <JCHEM_LOGP>
2.2210407536666668

> <ALOGPS_LOGS>
-2.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.603152565018943

> <JCHEM_PKA_STRONGEST_BASIC>
-5.610195346763434

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
59.165800000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.28e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{3-oxo-2-[(2E)-pent-2-en-1-yl]cyclopent-1-en-1-yl}acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030197
     RDKit          3D
(Z)-3-Oxo-2-(2-pentenyl)-1-cyclopenteneacetic acid
 31 31  0  0  0  0  0  0  0  0999 V2000
    4.3018    0.5686    0.0731 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7292   -0.6411   -0.6614 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3338   -0.3871   -1.1042 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3454   -1.1673   -0.6670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0628   -0.9611   -1.0747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9112   -0.6968    0.1149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6337    0.3773    0.3798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7504    1.5886   -0.4904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1929    1.7186   -0.8393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0482    2.1351   -0.0487 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5781    1.3468   -2.1279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3316    0.1940    1.7023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5333   -0.8816    2.3915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0623   -1.6673    1.2222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8150   -2.8896    1.0932 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3944    0.4577    0.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9122    0.6513    1.0953 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0175    1.4698   -0.4884 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7480   -1.4876    0.0448 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3738   -0.8754   -1.5136 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0864    0.4112   -1.7722 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5639   -1.9850    0.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3908   -1.9615   -1.4922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1851   -0.2156   -1.8599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1255    1.4892   -1.3808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4802    2.4840    0.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2184    1.9827   -2.5959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3675    1.1476    2.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3506   -0.2320    1.5179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1496   -1.4905    3.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6190   -0.4831    2.8982 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  7 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14  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
  8 25  1  0
  8 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 13 31  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      -0.002   6.724   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.147   5.694   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.826   4.187   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.971   3.157   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.651   1.651   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.830  -0.290   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      -0.615  -1.536   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  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.147  -1.375   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.060   3.620   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -3.052  -2.621   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -2.773   0.032   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    HMDB0030197
HETATM    1  C1  UNL     1       4.302   0.569   0.073  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.729  -0.641  -0.661  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.334  -0.387  -1.104  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.345  -1.167  -0.667  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.063  -0.961  -1.075  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.911  -0.697   0.115  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.634   0.377   0.380  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.750   1.589  -0.490  1.00  0.00           C  
HETATM    9  C9  UNL     1      -3.193   1.719  -0.839  1.00  0.00           C  
HETATM   10  O1  UNL     1      -4.048   2.135  -0.049  1.00  0.00           O  
HETATM   11  O2  UNL     1      -3.578   1.347  -2.128  1.00  0.00           O  
HETATM   12  C10 UNL     1      -2.332   0.194   1.702  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.533  -0.882   2.391  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.062  -1.667   1.222  1.00  0.00           C  
HETATM   15  O3  UNL     1      -0.815  -2.890   1.093  1.00  0.00           O  
HETATM   16  H1  UNL     1       5.394   0.458   0.099  1.00  0.00           H  
HETATM   17  H2  UNL     1       3.912   0.651   1.095  1.00  0.00           H  
HETATM   18  H3  UNL     1       4.018   1.470  -0.488  1.00  0.00           H  
HETATM   19  H4  UNL     1       3.748  -1.488   0.045  1.00  0.00           H  
HETATM   20  H5  UNL     1       4.374  -0.875  -1.514  1.00  0.00           H  
HETATM   21  H6  UNL     1       2.086   0.411  -1.772  1.00  0.00           H  
HETATM   22  H7  UNL     1       1.564  -1.985   0.011  1.00  0.00           H  
HETATM   23  H8  UNL     1      -0.391  -1.961  -1.492  1.00  0.00           H  
HETATM   24  H9  UNL     1      -0.185  -0.216  -1.860  1.00  0.00           H  
HETATM   25  H10 UNL     1      -1.126   1.489  -1.381  1.00  0.00           H  
HETATM   26  H11 UNL     1      -1.480   2.484   0.128  1.00  0.00           H  
HETATM   27  H12 UNL     1      -4.218   1.983  -2.596  1.00  0.00           H  
HETATM   28  H13 UNL     1      -2.368   1.148   2.261  1.00  0.00           H  
HETATM   29  H14 UNL     1      -3.351  -0.232   1.518  1.00  0.00           H  
HETATM   30  H15 UNL     1      -2.150  -1.490   3.084  1.00  0.00           H  
HETATM   31  H16 UNL     1      -0.619  -0.483   2.898  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    7   14
CONECT    7    8   12
CONECT    8    9   25   26
CONECT    9   10   10   11
CONECT   11   27
CONECT   12   13   28   29
CONECT   13   14   30   31
CONECT   14   15   15
END

HMDB0030197
     RDKit          3D
(Z)-3-Oxo-2-(2-pentenyl)-1-cyclopenteneacetic acid
 31 31  0  0  0  0  0  0  0  0999 V2000
    4.3018    0.5686    0.0731 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7292   -0.6411   -0.6614 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3338   -0.3871   -1.1042 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3454   -1.1673   -0.6670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0628   -0.9611   -1.0747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9112   -0.6968    0.1149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6337    0.3773    0.3798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7504    1.5886   -0.4904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1929    1.7186   -0.8393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0482    2.1351   -0.0487 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5781    1.3468   -2.1279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3316    0.1940    1.7023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5333   -0.8816    2.3915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0623   -1.6673    1.2222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8150   -2.8896    1.0932 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3944    0.4577    0.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9122    0.6513    1.0953 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0175    1.4698   -0.4884 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7480   -1.4876    0.0448 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3738   -0.8754   -1.5136 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0864    0.4112   -1.7722 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5639   -1.9850    0.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3908   -1.9615   -1.4922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1851   -0.2156   -1.8599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1255    1.4892   -1.3808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4802    2.4840    0.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2184    1.9827   -2.5959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3675    1.1476    2.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3506   -0.2320    1.5179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1496   -1.4905    3.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6190   -0.4831    2.8982 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  7 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14  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
  8 25  1  0
  8 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 13 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(Z)-3-oxo-2-(2-Pentenyl)-1-cyclopenteneacetate	Generator
2-{3-oxo-2-[(2E)-pent-2-en-1-yl]cyclopent-1-en-1-yl}acetate	HMDB

Chemical Formula

C₁₂H₁₆O₃

Average Molecular Weight

208.2536

Monoisotopic Molecular Weight

208.109944378

IUPAC Name

2-{3-oxo-2-[(2E)-pent-2-en-1-yl]cyclopent-1-en-1-yl}acetic acid

Traditional Name

{3-oxo-2-[(2E)-pent-2-en-1-yl]cyclopent-1-en-1-yl}acetic acid

CAS Registry Number

120282-76-0

SMILES

CC\C=C\CC1=C(CC(O)=O)CCC1=O

InChI Identifier

InChI=1S/C12H16O3/c1-2-3-4-5-10-9(8-12(14)15)6-7-11(10)13/h3-4H,2,5-8H2,1H3,(H,14,15)/b4-3+

InChI Key

QAAHGFINENUHAR-ONEGZZNKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclic ketones

Alternative Parents

Substituents

Cyclic ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0030197)
Cytoplasm (HMDB: HMDB0030197)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030197)

Source

Endogenous

Endogenous (HMDB: HMDB0030197)

Plant

Fabaceae (HMDB: HMDB0030197)

Exogenous

Food

Food (HMDB: HMDB0030197)

Pulse

Pulses (FooDB: FOOD00867)

Exogenous (HMDB: HMDB0030197)

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
Water Solubility	0.53 g/L	ALOGPS
logP	2.3	ALOGPS
logP	2.22	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	4.6	ChemAxon
pKa (Strongest Basic)	-5.6	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	5	ChemAxon
Refractivity	59.17 m³·mol⁻¹	ChemAxon
Polarizability	22.78 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]+	152.22	31661259
DarkChem	[M-H]-	148.586	31661259
DeepCCS	[M+H]+	145.567	30932474
DeepCCS	[M-H]-	142.765	30932474
DeepCCS	[M-2H]-	178.717	30932474
DeepCCS	[M+Na]+	154.255	30932474
AllCCS	[M+H]+	149.1	32859911
AllCCS	[M+H-H2O]+	145.3	32859911
AllCCS	[M+NH4]+	152.7	32859911
AllCCS	[M+Na]+	153.8	32859911
AllCCS	[M-H]-	151.1	32859911
AllCCS	[M+Na-2H]-	151.8	32859911
AllCCS	[M+HCOO]-	152.6	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.	5.86 minutes	32390414
Predicted by Siyang on May 30, 2022	12.612 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.08 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1939.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	326.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	147.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	205.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	122.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	449.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	461.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	94.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1106.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	403.7 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	1119.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	327.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	355.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	379.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	291.4 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	15.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(Z)-3-Oxo-2-(2-pentenyl)-1-cyclopenteneacetic acid	CC\C=C\CC1=C(CC(O)=O)CCC1=O	3023.0	Standard polar	33892256
(Z)-3-Oxo-2-(2-pentenyl)-1-cyclopenteneacetic acid	CC\C=C\CC1=C(CC(O)=O)CCC1=O	1708.5	Standard non polar	33892256
(Z)-3-Oxo-2-(2-pentenyl)-1-cyclopenteneacetic acid	CC\C=C\CC1=C(CC(O)=O)CCC1=O	1768.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(Z)-3-Oxo-2-(2-pentenyl)-1-cyclopenteneacetic acid,1TMS,isomer #1	CC/C=C/CC1=C(CC(=O)O[Si](C)(C)C)CCC1=O	1858.5	Semi standard non polar	33892256
(Z)-3-Oxo-2-(2-pentenyl)-1-cyclopenteneacetic acid,1TMS,isomer #2	CC/C=C/CC1=C(CC(=O)O)CC=C1O[Si](C)(C)C	1948.9	Semi standard non polar	33892256
(Z)-3-Oxo-2-(2-pentenyl)-1-cyclopenteneacetic acid,2TMS,isomer #1	CC/C=C/CC1=C(CC(=O)O[Si](C)(C)C)CC=C1O[Si](C)(C)C	1947.8	Semi standard non polar	33892256
(Z)-3-Oxo-2-(2-pentenyl)-1-cyclopenteneacetic acid,2TMS,isomer #1	CC/C=C/CC1=C(CC(=O)O[Si](C)(C)C)CC=C1O[Si](C)(C)C	1946.2	Standard non polar	33892256
(Z)-3-Oxo-2-(2-pentenyl)-1-cyclopenteneacetic acid,1TBDMS,isomer #1	CC/C=C/CC1=C(CC(=O)O[Si](C)(C)C(C)(C)C)CCC1=O	2104.4	Semi standard non polar	33892256
(Z)-3-Oxo-2-(2-pentenyl)-1-cyclopenteneacetic acid,1TBDMS,isomer #2	CC/C=C/CC1=C(CC(=O)O)CC=C1O[Si](C)(C)C(C)(C)C	2198.3	Semi standard non polar	33892256
(Z)-3-Oxo-2-(2-pentenyl)-1-cyclopenteneacetic acid,2TBDMS,isomer #1	CC/C=C/CC1=C(CC(=O)O[Si](C)(C)C(C)(C)C)CC=C1O[Si](C)(C)C(C)(C)C	2396.6	Semi standard non polar	33892256
(Z)-3-Oxo-2-(2-pentenyl)-1-cyclopenteneacetic acid,2TBDMS,isomer #1	CC/C=C/CC1=C(CC(=O)O[Si](C)(C)C(C)(C)C)CC=C1O[Si](C)(C)C(C)(C)C	2256.5	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (Z)-3-Oxo-2-(2-pentenyl)-1-cyclopenteneacetic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-06rx-4900000000-e1f19fc601f253d435a6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (Z)-3-Oxo-2-(2-pentenyl)-1-cyclopenteneacetic acid GC-MS (1 TMS) - 70eV, Positive	splash10-00y3-6390000000-d5776196040ab583d9a7	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (Z)-3-Oxo-2-(2-pentenyl)-1-cyclopenteneacetic 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-3-Oxo-2-(2-pentenyl)-1-cyclopenteneacetic acid 10V, Positive-QTOF	splash10-0a4l-1940000000-7e0f6552c86edba69fd1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-3-Oxo-2-(2-pentenyl)-1-cyclopenteneacetic acid 20V, Positive-QTOF	splash10-08fs-5900000000-2e8a3395963e1da39a50	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-3-Oxo-2-(2-pentenyl)-1-cyclopenteneacetic acid 40V, Positive-QTOF	splash10-1003-9200000000-7f82e8aab0f8ed530640	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-3-Oxo-2-(2-pentenyl)-1-cyclopenteneacetic acid 10V, Negative-QTOF	splash10-0bt9-0690000000-172eed6b333e1a0a7534	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-3-Oxo-2-(2-pentenyl)-1-cyclopenteneacetic acid 20V, Negative-QTOF	splash10-0bt9-2950000000-b4e55435a8f4fad21dca	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-3-Oxo-2-(2-pentenyl)-1-cyclopenteneacetic acid 40V, Negative-QTOF	splash10-0a4l-9300000000-59da33e05dd658f57d9c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-3-Oxo-2-(2-pentenyl)-1-cyclopenteneacetic acid 10V, Positive-QTOF	splash10-0595-3920000000-31a48ac3142d4afce718	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-3-Oxo-2-(2-pentenyl)-1-cyclopenteneacetic acid 20V, Positive-QTOF	splash10-0595-6900000000-4b6c20936a8219e772a1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-3-Oxo-2-(2-pentenyl)-1-cyclopenteneacetic acid 40V, Positive-QTOF	splash10-052f-9300000000-798b381973067e2b4f40	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-3-Oxo-2-(2-pentenyl)-1-cyclopenteneacetic acid 10V, Negative-QTOF	splash10-0a4i-9010000000-c2f8354480dad812f0b6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-3-Oxo-2-(2-pentenyl)-1-cyclopenteneacetic acid 20V, Negative-QTOF	splash10-0a4i-9000000000-ce877f2bf675460adb72	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-3-Oxo-2-(2-pentenyl)-1-cyclopenteneacetic acid 40V, Negative-QTOF	splash10-0006-9000000000-3ef212043751a87318f7	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB002015

KNApSAcK ID

C00054584

Chemspider ID

30776818

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14262444

PDB ID

Not Available

ChEBI ID

168229

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for (Z)-3-Oxo-2-(2-pentenyl)-1-cyclopenteneacetic acid (HMDB0030197)

MOL for HMDB0030197 ((Z)-3-Oxo-2-(2-pentenyl)-1-cyclopenteneacetic acid)

3D MOL for HMDB0030197 ((Z)-3-Oxo-2-(2-pentenyl)-1-cyclopenteneacetic acid)

3D SDF for HMDB0030197 ((Z)-3-Oxo-2-(2-pentenyl)-1-cyclopenteneacetic acid)

3D-SDF for HMDB0030197 ((Z)-3-Oxo-2-(2-pentenyl)-1-cyclopenteneacetic acid)

PDB for HMDB0030197 ((Z)-3-Oxo-2-(2-pentenyl)-1-cyclopenteneacetic acid)

3D PDB for HMDB0030197 ((Z)-3-Oxo-2-(2-pentenyl)-1-cyclopenteneacetic acid)

SMILES for HMDB0030197 ((Z)-3-Oxo-2-(2-pentenyl)-1-cyclopenteneacetic acid)

INCHI for HMDB0030197 ((Z)-3-Oxo-2-(2-pentenyl)-1-cyclopenteneacetic acid)

Structure for HMDB0030197 ((Z)-3-Oxo-2-(2-pentenyl)-1-cyclopenteneacetic acid)

3D Structure for HMDB0030197 ((Z)-3-Oxo-2-(2-pentenyl)-1-cyclopenteneacetic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra