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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:33:47 UTC

Update Date

2022-03-07 02:55:16 UTC

HMDB ID

HMDB0037325

Secondary Accession Numbers

HMDB37325

Metabolite Identification

Common Name

Achimilic acid

Description

Achimilic acid, also known as achimilate, belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain. Achimilic acid has been detected, but not quantified in, herbs and spices. This could make achimilic acid a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Achimilic acid.

Structure

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

HMDB0037325
     RDKit          3D
Achimilic acid
 38 38  0  0  0  0  0  0  0  0999 V2000
    0.3102    2.3682   -2.3819 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4064    2.1707   -1.0741 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3592    3.3171   -0.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4331    3.2853    1.0590 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2174    4.6069   -0.7422 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5510    0.7945   -0.5415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6197    0.5025    0.2480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5445   -0.3824   -0.0183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5837   -1.2397   -1.1591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7992   -1.3020   -2.1068 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7771   -2.1010   -1.0496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4164   -1.7993    0.0521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7533   -0.7230    0.8049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3870   -1.2893    2.1591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6178    0.3450    0.9061 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8501    0.7239    0.2150 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2485   -0.5330    0.8567 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4726   -1.6955   -0.0271 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8511   -2.2307   -0.2799 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5574   -2.2358   -0.5602 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1983    3.3606   -2.7803 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3368    1.5253   -3.0923 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2836    5.4393   -0.1846 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7327    0.1320   -1.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7652    1.0686    1.1709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0705   -2.8521   -1.7661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3478   -2.2744    0.4089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9889   -2.3162    2.0086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7523   -0.6232    2.7419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3766   -1.4289    2.6891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1534    1.0557    1.4189 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9078    1.5293    1.0103 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7163    1.0222   -0.4585 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2568   -0.3158    1.3389 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6268   -0.8160    1.7455 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8138   -3.0567   -1.0136 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3058   -2.5981    0.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5177   -1.4339   -0.6825 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  2  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
  6 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 13  8  1  0
  1 21  1  0
  1 22  1  0
  5 23  1  0
  6 24  1  0
  7 25  1  0
 11 26  1  0
 12 27  1  0
 14 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 16 33  1  0
 17 34  1  0
 17 35  1  0
 19 36  1  0
 19 37  1  0
 19 38  1  0
M  END

  Mrv0541 02241210282D          

 20 20  0  0  0  0            999 V2000
    0.8089   -0.9302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0515   -0.2019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4850    0.4451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2425    0.3638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8089    0.9302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6179    0.7683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9418   -0.0399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8089    1.2541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2433    1.9011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9418   -1.0922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2941   -1.5773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8089   -2.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0008   -1.9817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0008   -1.1728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7276   -0.8489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8605   -2.1437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1843    0.8496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6179    1.4160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8605    2.2250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1843    1.3347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1 11  1  0  0  0  0
  1 14  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  8  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 20  2  0  0  0  0
  8  9  2  0  0  0  0
  8 18  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 16  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037325

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)CCC(\C=C1/C(=O)C=CC1(C)O)C(=C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O5/c1-9(16)4-5-11(10(2)14(18)19)8-12-13(17)6-7-15(12,3)20/h6-8,11,20H,2,4-5H2,1,3H3,(H,18,19)/b12-8+

> <INCHI_KEY>
ARZDSTJTDVJYCF-XYOKQWHBSA-N

> <FORMULA>
C15H18O5

> <MOLECULAR_WEIGHT>
278.3004

> <EXACT_MASS>
278.115423686

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
28.391765705253746

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-{[(1Z)-2-hydroxy-2-methyl-5-oxocyclopent-3-en-1-ylidene]methyl}-2-methylidene-6-oxoheptanoic acid

> <ALOGPS_LOGP>
1.24

> <JCHEM_LOGP>
1.2908081929999997

> <ALOGPS_LOGS>
-2.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.815826822688074

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.449991008608951

> <JCHEM_PKA_STRONGEST_BASIC>
-3.316882629650249

> <JCHEM_POLAR_SURFACE_AREA>
91.66999999999999

> <JCHEM_REFRACTIVITY>
75.00319999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.22e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[(1Z)-2-hydroxy-2-methyl-5-oxocyclopent-3-en-1-ylidene]methyl}-2-methylidene-6-oxoheptanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037325
     RDKit          3D
Achimilic acid
 38 38  0  0  0  0  0  0  0  0999 V2000
    0.3102    2.3682   -2.3819 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4064    2.1707   -1.0741 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3592    3.3171   -0.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4331    3.2853    1.0590 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2174    4.6069   -0.7422 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5510    0.7945   -0.5415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6197    0.5025    0.2480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5445   -0.3824   -0.0183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5837   -1.2397   -1.1591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7992   -1.3020   -2.1068 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7771   -2.1010   -1.0496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4164   -1.7993    0.0521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7533   -0.7230    0.8049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3870   -1.2893    2.1591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6178    0.3450    0.9061 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8501    0.7239    0.2150 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2485   -0.5330    0.8567 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4726   -1.6955   -0.0271 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8511   -2.2307   -0.2799 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5574   -2.2358   -0.5602 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1983    3.3606   -2.7803 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3368    1.5253   -3.0923 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2836    5.4393   -0.1846 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7327    0.1320   -1.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7652    1.0686    1.1709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0705   -2.8521   -1.7661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3478   -2.2744    0.4089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9889   -2.3162    2.0086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7523   -0.6232    2.7419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3766   -1.4289    2.6891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1534    1.0557    1.4189 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9078    1.5293    1.0103 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7163    1.0222   -0.4585 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2568   -0.3158    1.3389 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6268   -0.8160    1.7455 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8138   -3.0567   -1.0136 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3058   -2.5981    0.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5177   -1.4339   -0.6825 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  2  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
  6 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 13  8  1  0
  1 21  1  0
  1 22  1  0
  5 23  1  0
  6 24  1  0
  7 25  1  0
 11 26  1  0
 12 27  1  0
 14 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 16 33  1  0
 17 34  1  0
 17 35  1  0
 19 36  1  0
 19 37  1  0
 19 38  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       1.510  -1.736   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.963  -0.377   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.905   0.831   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.453   0.679   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.510   1.736   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.020   1.434   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.625  -0.074   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.510   2.341   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.454   3.549   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.625  -2.039   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.416  -2.944   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.510  -4.153   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.001  -3.699   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.001  -2.189   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.358  -1.585   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       3.473  -4.002   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       4.077   1.586   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.020   2.643   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.473   4.153   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -4.077   2.491   0.000  0.00  0.00           O+0
CONECT    1    2   11   14                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   20                                                  
CONECT    7    6                                                            
CONECT    8    3    9   18                                                  
CONECT    9    8                                                            
CONECT   10   11                                                            
CONECT   11    1   10   12   16                                             
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14    1   13   15                                                  
CONECT   15   14                                                            
CONECT   16   11                                                            
CONECT   17   18                                                            
CONECT   18    8   17   19                                                  
CONECT   19   18                                                            
CONECT   20    6                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

COMPND    HMDB0037325
HETATM    1  C1  UNL     1       0.310   2.368  -2.382  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.406   2.171  -1.074  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.359   3.317  -0.188  1.00  0.00           C  
HETATM    4  O1  UNL     1       0.433   3.285   1.059  1.00  0.00           O  
HETATM    5  O2  UNL     1       0.217   4.607  -0.742  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.551   0.794  -0.542  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.620   0.503   0.248  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.544  -0.382  -0.018  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.584  -1.240  -1.159  1.00  0.00           C  
HETATM   10  O3  UNL     1      -0.799  -1.302  -2.107  1.00  0.00           O  
HETATM   11  C8  UNL     1      -2.777  -2.101  -1.050  1.00  0.00           C  
HETATM   12  C9  UNL     1      -3.416  -1.799   0.052  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.753  -0.723   0.805  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.387  -1.289   2.159  1.00  0.00           C  
HETATM   15  O4  UNL     1      -3.618   0.345   0.906  1.00  0.00           O  
HETATM   16  C12 UNL     1       1.850   0.724   0.215  1.00  0.00           C  
HETATM   17  C13 UNL     1       2.248  -0.533   0.857  1.00  0.00           C  
HETATM   18  C14 UNL     1       2.473  -1.695  -0.027  1.00  0.00           C  
HETATM   19  C15 UNL     1       3.851  -2.231  -0.280  1.00  0.00           C  
HETATM   20  O5  UNL     1       1.557  -2.236  -0.560  1.00  0.00           O  
HETATM   21  H1  UNL     1       0.198   3.361  -2.780  1.00  0.00           H  
HETATM   22  H2  UNL     1       0.337   1.525  -3.092  1.00  0.00           H  
HETATM   23  H3  UNL     1       0.284   5.439  -0.185  1.00  0.00           H  
HETATM   24  H4  UNL     1       0.733   0.132  -1.409  1.00  0.00           H  
HETATM   25  H5  UNL     1      -0.765   1.069   1.171  1.00  0.00           H  
HETATM   26  H6  UNL     1      -3.070  -2.852  -1.766  1.00  0.00           H  
HETATM   27  H7  UNL     1      -4.348  -2.274   0.409  1.00  0.00           H  
HETATM   28  H8  UNL     1      -1.989  -2.316   2.009  1.00  0.00           H  
HETATM   29  H9  UNL     1      -1.752  -0.623   2.742  1.00  0.00           H  
HETATM   30  H10 UNL     1      -3.377  -1.429   2.689  1.00  0.00           H  
HETATM   31  H11 UNL     1      -3.153   1.056   1.419  1.00  0.00           H  
HETATM   32  H12 UNL     1       1.908   1.529   1.010  1.00  0.00           H  
HETATM   33  H13 UNL     1       2.716   1.022  -0.458  1.00  0.00           H  
HETATM   34  H14 UNL     1       3.257  -0.316   1.339  1.00  0.00           H  
HETATM   35  H15 UNL     1       1.627  -0.816   1.745  1.00  0.00           H  
HETATM   36  H16 UNL     1       3.814  -3.057  -1.014  1.00  0.00           H  
HETATM   37  H17 UNL     1       4.306  -2.598   0.681  1.00  0.00           H  
HETATM   38  H18 UNL     1       4.518  -1.434  -0.683  1.00  0.00           H  
CONECT    1    2    2   21   22
CONECT    2    3    6
CONECT    3    4    4    5
CONECT    5   23
CONECT    6    7   16   24
CONECT    7    8    8   25
CONECT    8    9   13
CONECT    9   10   10   11
CONECT   11   12   12   26
CONECT   12   13   27
CONECT   13   14   15
CONECT   14   28   29   30
CONECT   15   31
CONECT   16   17   32   33
CONECT   17   18   34   35
CONECT   18   19   20   20
CONECT   19   36   37   38
END

HMDB0037325
     RDKit          3D
Achimilic acid
 38 38  0  0  0  0  0  0  0  0999 V2000
    0.3102    2.3682   -2.3819 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4064    2.1707   -1.0741 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3592    3.3171   -0.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4331    3.2853    1.0590 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2174    4.6069   -0.7422 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5510    0.7945   -0.5415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6197    0.5025    0.2480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5445   -0.3824   -0.0183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5837   -1.2397   -1.1591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7992   -1.3020   -2.1068 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7771   -2.1010   -1.0496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4164   -1.7993    0.0521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7533   -0.7230    0.8049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3870   -1.2893    2.1591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6178    0.3450    0.9061 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8501    0.7239    0.2150 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2485   -0.5330    0.8567 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4726   -1.6955   -0.0271 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8511   -2.2307   -0.2799 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5574   -2.2358   -0.5602 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1983    3.3606   -2.7803 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3368    1.5253   -3.0923 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2836    5.4393   -0.1846 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7327    0.1320   -1.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7652    1.0686    1.1709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0705   -2.8521   -1.7661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3478   -2.2744    0.4089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9889   -2.3162    2.0086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7523   -0.6232    2.7419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3766   -1.4289    2.6891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1534    1.0557    1.4189 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9078    1.5293    1.0103 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7163    1.0222   -0.4585 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2568   -0.3158    1.3389 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6268   -0.8160    1.7455 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8138   -3.0567   -1.0136 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3058   -2.5981    0.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5177   -1.4339   -0.6825 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  2  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
  6 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 13  8  1  0
  1 21  1  0
  1 22  1  0
  5 23  1  0
  6 24  1  0
  7 25  1  0
 11 26  1  0
 12 27  1  0
 14 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 16 33  1  0
 17 34  1  0
 17 35  1  0
 19 36  1  0
 19 37  1  0
 19 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Achimilate	Generator
3-[(2-Hydroxy-2-methyl-5-oxo-3-cyclopenten-1-ylidene)methyl]-2-methylene-6-oxoheptanoic acid, 9ci	HMDB
3-{[(1Z)-2-hydroxy-2-methyl-5-oxocyclopent-3-en-1-ylidene]methyl}-2-methylidene-6-oxoheptanoate	HMDB
Achimillate b	Generator

Chemical Formula

C₁₅H₁₈O₅

Average Molecular Weight

278.3004

Monoisotopic Molecular Weight

278.115423686

IUPAC Name

3-{[(1Z)-2-hydroxy-2-methyl-5-oxocyclopent-3-en-1-ylidene]methyl}-2-methylidene-6-oxoheptanoic acid

Traditional Name

3-{[(1Z)-2-hydroxy-2-methyl-5-oxocyclopent-3-en-1-ylidene]methyl}-2-methylidene-6-oxoheptanoic acid

CAS Registry Number

110732-04-2

SMILES

CC(=O)CCC(\C=C1/C(=O)C=CC1(C)O)C(=C)C(O)=O

InChI Identifier

InChI=1S/C15H18O5/c1-9(16)4-5-11(10(2)14(18)19)8-12-13(17)6-7-15(12,3)20/h6-8,11,20H,2,4-5H2,1,3H3,(H,18,19)/b12-8+

InChI Key

ARZDSTJTDVJYCF-XYOKQWHBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Medium-chain keto acids and derivatives

Direct Parent

Medium-chain keto acids and derivatives

Alternative Parents

Substituents

Medium-chain keto acid
Branched fatty acid
Hydroxy fatty acid
Fatty acyl
Unsaturated fatty acid
Tertiary alcohol
Ketone
Cyclic ketone
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Alcohol
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0037325)

Food

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

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	0.62 g/L	ALOGPS
logP	1.24	ALOGPS
logP	1.29	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	4.45	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	91.67 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	75 m³·mol⁻¹	ChemAxon
Polarizability	28.39 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
DeepCCS	[M+H]+	169.169	30932474
DeepCCS	[M-H]-	166.811	30932474
DeepCCS	[M-2H]-	199.697	30932474
DeepCCS	[M+Na]+	175.262	30932474
AllCCS	[M+H]+	164.9	32859911
AllCCS	[M+H-H2O]+	161.6	32859911
AllCCS	[M+NH4]+	168.1	32859911
AllCCS	[M+Na]+	169.0	32859911
AllCCS	[M-H]-	165.9	32859911
AllCCS	[M+Na-2H]-	166.2	32859911
AllCCS	[M+HCOO]-	166.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Achimilic acid	CC(=O)CCC(\C=C1/C(=O)C=CC1(C)O)C(=C)C(O)=O	3948.2	Standard polar	33892256
Achimilic acid	CC(=O)CCC(\C=C1/C(=O)C=CC1(C)O)C(=C)C(O)=O	1900.2	Standard non polar	33892256
Achimilic acid	CC(=O)CCC(\C=C1/C(=O)C=CC1(C)O)C(=C)C(O)=O	2146.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Achimilic acid,1TMS,isomer #1	C=C(C(=O)O)C(/C=C1\C(=O)C=CC1(C)O[Si](C)(C)C)CCC(C)=O	2286.9	Semi standard non polar	33892256
Achimilic acid,1TMS,isomer #2	C=C(C(=O)O[Si](C)(C)C)C(/C=C1\C(=O)C=CC1(C)O)CCC(C)=O	2207.2	Semi standard non polar	33892256
Achimilic acid,1TMS,isomer #3	C=C(C(=O)O)C(/C=C1\C(=O)C=CC1(C)O)CC=C(C)O[Si](C)(C)C	2439.6	Semi standard non polar	33892256
Achimilic acid,1TMS,isomer #4	C=C(CCC(/C=C1\C(=O)C=CC1(C)O)C(=C)C(=O)O)O[Si](C)(C)C	2336.6	Semi standard non polar	33892256
Achimilic acid,2TMS,isomer #1	C=C(C(=O)O[Si](C)(C)C)C(/C=C1\C(=O)C=CC1(C)O[Si](C)(C)C)CCC(C)=O	2252.2	Semi standard non polar	33892256
Achimilic acid,2TMS,isomer #2	C=C(C(=O)O)C(/C=C1\C(=O)C=CC1(C)O[Si](C)(C)C)CC=C(C)O[Si](C)(C)C	2460.1	Semi standard non polar	33892256
Achimilic acid,2TMS,isomer #3	C=C(CCC(/C=C1\C(=O)C=CC1(C)O[Si](C)(C)C)C(=C)C(=O)O)O[Si](C)(C)C	2377.8	Semi standard non polar	33892256
Achimilic acid,2TMS,isomer #4	C=C(C(=O)O[Si](C)(C)C)C(/C=C1\C(=O)C=CC1(C)O)CC=C(C)O[Si](C)(C)C	2361.8	Semi standard non polar	33892256
Achimilic acid,2TMS,isomer #5	C=C(CCC(/C=C1\C(=O)C=CC1(C)O)C(=C)C(=O)O[Si](C)(C)C)O[Si](C)(C)C	2288.9	Semi standard non polar	33892256
Achimilic acid,3TMS,isomer #1	C=C(C(=O)O[Si](C)(C)C)C(/C=C1\C(=O)C=CC1(C)O[Si](C)(C)C)CC=C(C)O[Si](C)(C)C	2419.6	Semi standard non polar	33892256
Achimilic acid,3TMS,isomer #1	C=C(C(=O)O[Si](C)(C)C)C(/C=C1\C(=O)C=CC1(C)O[Si](C)(C)C)CC=C(C)O[Si](C)(C)C	2231.9	Standard non polar	33892256
Achimilic acid,3TMS,isomer #2	C=C(CCC(/C=C1\C(=O)C=CC1(C)O[Si](C)(C)C)C(=C)C(=O)O[Si](C)(C)C)O[Si](C)(C)C	2356.5	Semi standard non polar	33892256
Achimilic acid,3TMS,isomer #2	C=C(CCC(/C=C1\C(=O)C=CC1(C)O[Si](C)(C)C)C(=C)C(=O)O[Si](C)(C)C)O[Si](C)(C)C	2225.4	Standard non polar	33892256
Achimilic acid,1TBDMS,isomer #1	C=C(C(=O)O)C(/C=C1\C(=O)C=CC1(C)O[Si](C)(C)C(C)(C)C)CCC(C)=O	2526.3	Semi standard non polar	33892256
Achimilic acid,1TBDMS,isomer #2	C=C(C(=O)O[Si](C)(C)C(C)(C)C)C(/C=C1\C(=O)C=CC1(C)O)CCC(C)=O	2454.0	Semi standard non polar	33892256
Achimilic acid,1TBDMS,isomer #3	C=C(C(=O)O)C(/C=C1\C(=O)C=CC1(C)O)CC=C(C)O[Si](C)(C)C(C)(C)C	2692.6	Semi standard non polar	33892256
Achimilic acid,1TBDMS,isomer #4	C=C(CCC(/C=C1\C(=O)C=CC1(C)O)C(=C)C(=O)O)O[Si](C)(C)C(C)(C)C	2588.0	Semi standard non polar	33892256
Achimilic acid,2TBDMS,isomer #1	C=C(C(=O)O[Si](C)(C)C(C)(C)C)C(/C=C1\C(=O)C=CC1(C)O[Si](C)(C)C(C)(C)C)CCC(C)=O	2731.5	Semi standard non polar	33892256
Achimilic acid,2TBDMS,isomer #2	C=C(C(=O)O)C(/C=C1\C(=O)C=CC1(C)O[Si](C)(C)C(C)(C)C)CC=C(C)O[Si](C)(C)C(C)(C)C	2953.1	Semi standard non polar	33892256
Achimilic acid,2TBDMS,isomer #3	C=C(CCC(/C=C1\C(=O)C=CC1(C)O[Si](C)(C)C(C)(C)C)C(=C)C(=O)O)O[Si](C)(C)C(C)(C)C	2870.8	Semi standard non polar	33892256
Achimilic acid,2TBDMS,isomer #4	C=C(C(=O)O[Si](C)(C)C(C)(C)C)C(/C=C1\C(=O)C=CC1(C)O)CC=C(C)O[Si](C)(C)C(C)(C)C	2849.0	Semi standard non polar	33892256
Achimilic acid,2TBDMS,isomer #5	C=C(CCC(/C=C1\C(=O)C=CC1(C)O)C(=C)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2765.2	Semi standard non polar	33892256
Achimilic acid,3TBDMS,isomer #1	C=C(C(=O)O[Si](C)(C)C(C)(C)C)C(/C=C1\C(=O)C=CC1(C)O[Si](C)(C)C(C)(C)C)CC=C(C)O[Si](C)(C)C(C)(C)C	3109.8	Semi standard non polar	33892256
Achimilic acid,3TBDMS,isomer #1	C=C(C(=O)O[Si](C)(C)C(C)(C)C)C(/C=C1\C(=O)C=CC1(C)O[Si](C)(C)C(C)(C)C)CC=C(C)O[Si](C)(C)C(C)(C)C	2755.6	Standard non polar	33892256
Achimilic acid,3TBDMS,isomer #2	C=C(CCC(/C=C1\C(=O)C=CC1(C)O[Si](C)(C)C(C)(C)C)C(=C)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3038.2	Semi standard non polar	33892256
Achimilic acid,3TBDMS,isomer #2	C=C(CCC(/C=C1\C(=O)C=CC1(C)O[Si](C)(C)C(C)(C)C)C(=C)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2725.1	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Achimilic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-03dl-6190000000-0d5b8eb640ff576248c3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Achimilic acid GC-MS (2 TMS) - 70eV, Positive	splash10-0a6u-9208500000-9e902ed3a8a844cfbfce	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Achimilic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Achimilic 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 - Achimilic acid 10V, Positive-QTOF	splash10-03fr-0190000000-3a1b079344a573c90063	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Achimilic acid 20V, Positive-QTOF	splash10-02vl-0490000000-6c960a58d59868ebb484	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Achimilic acid 40V, Positive-QTOF	splash10-0002-2920000000-cef3756ff61f94fa4543	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Achimilic acid 10V, Negative-QTOF	splash10-004i-0090000000-42b3d2c439b996e96f8b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Achimilic acid 20V, Negative-QTOF	splash10-06ur-2390000000-c1b24a13577310d5eeb1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Achimilic acid 40V, Negative-QTOF	splash10-0a4i-8930000000-accf60b948f3d2411749	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Achimilic acid 10V, Negative-QTOF	splash10-004i-2290000000-2a1f57345e51cf0ca27a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Achimilic acid 20V, Negative-QTOF	splash10-05g0-3930000000-8ca1c61228bf139f494c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Achimilic acid 40V, Negative-QTOF	splash10-0019-3910000000-ca1bffee9597b4b3e429	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Achimilic acid 10V, Positive-QTOF	splash10-0200-0490000000-bf1c3b52291e8578367b	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Achimilic acid 20V, Positive-QTOF	splash10-0006-1690000000-36cc43ced36db95cc1f5	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Achimilic acid 40V, Positive-QTOF	splash10-0a4j-5910000000-5ed5a9ded54b0d96649e	2021-09-25	Wishart 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

FDB020566

KNApSAcK ID

C00054662

Chemspider ID

35014401

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752170

PDB ID

Not Available

ChEBI ID

174657

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 Achimilic acid (HMDB0037325)

MOL for HMDB0037325 (Achimilic acid)

3D MOL for HMDB0037325 (Achimilic acid)

3D SDF for HMDB0037325 (Achimilic acid)

3D-SDF for HMDB0037325 (Achimilic acid)

PDB for HMDB0037325 (Achimilic acid)

3D PDB for HMDB0037325 (Achimilic acid)

SMILES for HMDB0037325 (Achimilic acid)

INCHI for HMDB0037325 (Achimilic acid)

Structure for HMDB0037325 (Achimilic acid)

3D Structure for HMDB0037325 (Achimilic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra