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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:40:13 UTC

Update Date

2022-03-07 02:52:46 UTC

HMDB ID

HMDB0030987

Secondary Accession Numbers

HMDB30987

Metabolite Identification

Common Name

2-Carboxy-4-dodecanolide

Description

2-Carboxy-4-dodecanolide, also known as a-carboxy-g-dodecalactone, belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Based on a literature review very few articles have been published on 2-Carboxy-4-dodecanolide.

Structure

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

HMDB0030987
     RDKit          3D
2-Carboxy-4-dodecanolide
 39 39  0  0  0  0  0  0  0  0999 V2000
   -4.0602    2.1910    0.7990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0907    0.7356    1.1490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7242    0.1420    0.7525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5173    0.3301   -0.7185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1720   -0.2134   -1.1329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0415   -1.6682   -0.8590 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2253   -2.3093   -1.2113 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4832   -2.0967   -0.4841 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9659   -0.7353   -0.3103 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809   -0.7510    0.3893 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4675    0.7409    0.6241 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5568    1.1497    1.4814 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3527    0.3283    1.9800 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7349    2.4869    1.7666 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1169    0.9994    1.2133 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7488    1.9632    1.9248 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3210   -0.0637    0.8109 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0934    2.6880    1.0451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8588    2.7732    1.3407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2598    2.3785   -0.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3038    0.5782    2.2087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8855    0.2567    0.5400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9559    0.6598    1.3327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7383   -0.9447    1.0232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6037    1.4026   -0.9648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3071   -0.2659   -1.2373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3517    0.4065   -0.8114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2034   -0.0838   -2.2887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9191   -2.2080   -1.3161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2154   -1.8498    0.2544 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3660   -2.0776   -2.3363 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0100   -3.4401   -1.3012 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3489   -2.5183    0.5771 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2826   -2.7900   -0.9165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0761   -0.1088   -1.1765 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1247   -1.1419   -0.2981 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3044   -1.3350    1.3249 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4529    1.2161   -0.3762 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9823    3.1745    1.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 11 15  1  0
 15 16  2  0
 15 17  1  0
 17  9  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 14 39  1  0
M  END


  Mrv0541 05061305382D          

 17 17  0  0  0  0            999 V2000
    3.5108   -4.3205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2253   -3.9080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9398   -4.3205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6542   -3.9080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3687   -4.3205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0832   -3.9080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7976   -4.3205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5121   -3.9080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9803   -3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2266   -4.3205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5323   -4.5980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3528   -4.5118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1198   -5.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6883   -3.7581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8377   -5.1792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4554   -6.0662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3128   -5.1410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
 10  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11  9  1  0  0  0  0
 12 11  1  0  0  0  0
 13 11  1  0  0  0  0
 14 12  2  0  0  0  0
 15 12  1  0  0  0  0
 16 13  2  0  0  0  0
 17 10  1  0  0  0  0
 17 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030987

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCCC1CC(C(O)=O)C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C13H22O4/c1-2-3-4-5-6-7-8-10-9-11(12(14)15)13(16)17-10/h10-11H,2-9H2,1H3,(H,14,15)

> <INCHI_KEY>
FMXVFWDIAZJILA-UHFFFAOYSA-N

> <FORMULA>
C13H22O4

> <MOLECULAR_WEIGHT>
242.3114

> <EXACT_MASS>
242.151809192

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.462883281616065

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-octyl-2-oxooxolane-3-carboxylic acid

> <ALOGPS_LOGP>
3.40

> <JCHEM_LOGP>
3.4907395926666664

> <ALOGPS_LOGS>
-3.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.093556602172378

> <JCHEM_PKA_STRONGEST_BASIC>
-7.196951635837937

> <JCHEM_POLAR_SURFACE_AREA>
63.599999999999994

> <JCHEM_REFRACTIVITY>
63.148600000000016

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.58e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-octyl-2-oxooxolane-3-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030987
     RDKit          3D
2-Carboxy-4-dodecanolide
 39 39  0  0  0  0  0  0  0  0999 V2000
   -4.0602    2.1910    0.7990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0907    0.7356    1.1490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7242    0.1420    0.7525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5173    0.3301   -0.7185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1720   -0.2134   -1.1329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0415   -1.6682   -0.8590 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2253   -2.3093   -1.2113 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4832   -2.0967   -0.4841 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9659   -0.7353   -0.3103 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809   -0.7510    0.3893 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4675    0.7409    0.6241 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5568    1.1497    1.4814 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3527    0.3283    1.9800 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7349    2.4869    1.7666 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1169    0.9994    1.2133 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7488    1.9632    1.9248 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3210   -0.0637    0.8109 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0934    2.6880    1.0451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8588    2.7732    1.3407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2598    2.3785   -0.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3038    0.5782    2.2087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8855    0.2567    0.5400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9559    0.6598    1.3327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7383   -0.9447    1.0232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6037    1.4026   -0.9648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3071   -0.2659   -1.2373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3517    0.4065   -0.8114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2034   -0.0838   -2.2887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9191   -2.2080   -1.3161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2154   -1.8498    0.2544 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3660   -2.0776   -2.3363 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0100   -3.4401   -1.3012 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3489   -2.5183    0.5771 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2826   -2.7900   -0.9165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0761   -0.1088   -1.1765 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1247   -1.1419   -0.2981 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3044   -1.3350    1.3249 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4529    1.2161   -0.3762 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9823    3.1745    1.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 11 15  1  0
 15 16  2  0
 15 17  1  0
 17  9  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 14 39  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       6.553  -8.065   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.887  -7.295   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.221  -8.065   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.555  -7.295   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.888  -8.065   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.222  -7.295   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.556  -8.065   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.889  -7.295   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      18.630  -7.438   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      17.223  -8.065   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      19.660  -8.583   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      21.192  -8.422   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      18.890  -9.917   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      21.818  -7.015   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      22.097  -9.668   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      19.517 -11.324   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      17.384  -9.597   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    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7   10                                                       
CONECT    9   10   11                                                       
CONECT   10    8    9   17                                                  
CONECT   11    9   12   13                                                  
CONECT   12   11   14   15                                                  
CONECT   13   11   16   17                                                  
CONECT   14   12                                                            
CONECT   15   12                                                            
CONECT   16   13                                                            
CONECT   17   10   13                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0030987
HETATM    1  C1  UNL     1      -4.060   2.191   0.799  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.091   0.736   1.149  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.724   0.142   0.753  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.517   0.330  -0.719  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.172  -0.213  -1.133  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.042  -1.668  -0.859  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.225  -2.309  -1.211  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.483  -2.097  -0.484  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.966  -0.735  -0.310  1.00  0.00           C  
HETATM   10  C10 UNL     1       3.381  -0.751   0.389  1.00  0.00           C  
HETATM   11  C11 UNL     1       3.468   0.741   0.624  1.00  0.00           C  
HETATM   12  C12 UNL     1       4.557   1.150   1.481  1.00  0.00           C  
HETATM   13  O1  UNL     1       5.353   0.328   1.980  1.00  0.00           O  
HETATM   14  O2  UNL     1       4.735   2.487   1.767  1.00  0.00           O  
HETATM   15  C13 UNL     1       2.117   0.999   1.213  1.00  0.00           C  
HETATM   16  O3  UNL     1       1.749   1.963   1.925  1.00  0.00           O  
HETATM   17  O4  UNL     1       1.321  -0.064   0.811  1.00  0.00           O  
HETATM   18  H1  UNL     1      -3.093   2.688   1.045  1.00  0.00           H  
HETATM   19  H2  UNL     1      -4.859   2.773   1.341  1.00  0.00           H  
HETATM   20  H3  UNL     1      -4.260   2.379  -0.280  1.00  0.00           H  
HETATM   21  H4  UNL     1      -4.304   0.578   2.209  1.00  0.00           H  
HETATM   22  H5  UNL     1      -4.886   0.257   0.540  1.00  0.00           H  
HETATM   23  H6  UNL     1      -1.956   0.660   1.333  1.00  0.00           H  
HETATM   24  H7  UNL     1      -2.738  -0.945   1.023  1.00  0.00           H  
HETATM   25  H8  UNL     1      -2.604   1.403  -0.965  1.00  0.00           H  
HETATM   26  H9  UNL     1      -3.307  -0.266  -1.237  1.00  0.00           H  
HETATM   27  H10 UNL     1      -0.352   0.406  -0.811  1.00  0.00           H  
HETATM   28  H11 UNL     1      -1.203  -0.084  -2.289  1.00  0.00           H  
HETATM   29  H12 UNL     1      -1.919  -2.208  -1.316  1.00  0.00           H  
HETATM   30  H13 UNL     1      -1.215  -1.850   0.254  1.00  0.00           H  
HETATM   31  H14 UNL     1       0.366  -2.078  -2.336  1.00  0.00           H  
HETATM   32  H15 UNL     1       0.010  -3.440  -1.301  1.00  0.00           H  
HETATM   33  H16 UNL     1       1.349  -2.518   0.577  1.00  0.00           H  
HETATM   34  H17 UNL     1       2.283  -2.790  -0.916  1.00  0.00           H  
HETATM   35  H18 UNL     1       2.076  -0.109  -1.177  1.00  0.00           H  
HETATM   36  H19 UNL     1       4.125  -1.142  -0.298  1.00  0.00           H  
HETATM   37  H20 UNL     1       3.304  -1.335   1.325  1.00  0.00           H  
HETATM   38  H21 UNL     1       3.453   1.216  -0.376  1.00  0.00           H  
HETATM   39  H22 UNL     1       4.982   3.175   1.054  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3   21   22
CONECT    3    4   23   24
CONECT    4    5   25   26
CONECT    5    6   27   28
CONECT    6    7   29   30
CONECT    7    8   31   32
CONECT    8    9   33   34
CONECT    9   10   17   35
CONECT   10   11   36   37
CONECT   11   12   15   38
CONECT   12   13   13   14
CONECT   14   39
CONECT   15   16   16   17
END

HMDB0030987
     RDKit          3D
2-Carboxy-4-dodecanolide
 39 39  0  0  0  0  0  0  0  0999 V2000
   -4.0602    2.1910    0.7990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0907    0.7356    1.1490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7242    0.1420    0.7525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5173    0.3301   -0.7185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1720   -0.2134   -1.1329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0415   -1.6682   -0.8590 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2253   -2.3093   -1.2113 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4832   -2.0967   -0.4841 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9659   -0.7353   -0.3103 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809   -0.7510    0.3893 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4675    0.7409    0.6241 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5568    1.1497    1.4814 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3527    0.3283    1.9800 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7349    2.4869    1.7666 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1169    0.9994    1.2133 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7488    1.9632    1.9248 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3210   -0.0637    0.8109 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0934    2.6880    1.0451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8588    2.7732    1.3407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2598    2.3785   -0.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3038    0.5782    2.2087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8855    0.2567    0.5400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9559    0.6598    1.3327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7383   -0.9447    1.0232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6037    1.4026   -0.9648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3071   -0.2659   -1.2373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3517    0.4065   -0.8114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2034   -0.0838   -2.2887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9191   -2.2080   -1.3161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2154   -1.8498    0.2544 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3660   -2.0776   -2.3363 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0100   -3.4401   -1.3012 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3489   -2.5183    0.5771 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2826   -2.7900   -0.9165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0761   -0.1088   -1.1765 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1247   -1.1419   -0.2981 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3044   -1.3350    1.3249 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4529    1.2161   -0.3762 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9823    3.1745    1.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 11 15  1  0
 15 16  2  0
 15 17  1  0
 17  9  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 14 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
a-Carboxy-g-dodecalactone	HMDB
5-Octyl-2-oxooxolane-3-carboxylate	HMDB

Chemical Formula

C₁₃H₂₂O₄

Average Molecular Weight

242.3114

Monoisotopic Molecular Weight

242.151809192

IUPAC Name

5-octyl-2-oxooxolane-3-carboxylic acid

Traditional Name

5-octyl-2-oxooxolane-3-carboxylic acid

CAS Registry Number

Not Available

SMILES

CCCCCCCCC1CC(C(O)=O)C(=O)O1

InChI Identifier

InChI=1S/C13H22O4/c1-2-3-4-5-6-7-8-10-9-11(12(14)15)13(16)17-10/h10-11H,2-9H2,1H3,(H,14,15)

InChI Key

FMXVFWDIAZJILA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

1,3-dicarbonyl compound
Gamma butyrolactone
Dicarboxylic acid or derivatives
Tetrahydrofuran
Carboxylic acid ester
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0030987)
Cell membrane (HMDB: HMDB0030987)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030987)

Source

Endogenous

Endogenous (HMDB: HMDB0030987)

Animal

Animal (HMDB: HMDB0030987)

Exogenous

Food

Food (HMDB: HMDB0030987)

Milk and milk product

Milk and milk products (FooDB: FOOD00863)

Exogenous (HMDB: HMDB0030987)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	68.5 - 70.5 °C	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	0.096 g/L	ALOGPS
logP	3.4	ALOGPS
logP	3.49	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	4.09	ChemAxon
pKa (Strongest Basic)	-7.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	63.15 m³·mol⁻¹	ChemAxon
Polarizability	27.46 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]+	161.848	31661259
DarkChem	[M-H]-	159.637	31661259
DeepCCS	[M+H]+	165.474	30932474
DeepCCS	[M-H]-	161.646	30932474
DeepCCS	[M-2H]-	198.234	30932474
DeepCCS	[M+Na]+	174.289	30932474
AllCCS	[M+H]+	160.5	32859911
AllCCS	[M+H-H2O]+	156.9	32859911
AllCCS	[M+NH4]+	163.8	32859911
AllCCS	[M+Na]+	164.8	32859911
AllCCS	[M-H]-	162.7	32859911
AllCCS	[M+Na-2H]-	163.3	32859911
AllCCS	[M+HCOO]-	164.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	8.13 minutes	32390414
Predicted by Siyang on May 30, 2022	16.6644 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.22 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2550.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	442.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	183.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	247.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	454.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	749.4 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	781.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	85.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1459.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	509.6 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	1602.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	501.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	434.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	521.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	444.1 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	50.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Carboxy-4-dodecanolide	CCCCCCCCC1CC(C(O)=O)C(=O)O1	3073.7	Standard polar	33892256
2-Carboxy-4-dodecanolide	CCCCCCCCC1CC(C(O)=O)C(=O)O1	1901.8	Standard non polar	33892256
2-Carboxy-4-dodecanolide	CCCCCCCCC1CC(C(O)=O)C(=O)O1	2049.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Carboxy-4-dodecanolide,1TMS,isomer #1	CCCCCCCCC1CC(C(=O)O[Si](C)(C)C)C(=O)O1	1948.1	Semi standard non polar	33892256
2-Carboxy-4-dodecanolide,1TBDMS,isomer #1	CCCCCCCCC1CC(C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O1	2210.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Carboxy-4-dodecanolide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0007-9500000000-cb666749a2c66cf9dd06	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Carboxy-4-dodecanolide GC-MS (1 TMS) - 70eV, Positive	splash10-0072-9120000000-77620c5921a1c9b375c8	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Carboxy-4-dodecanolide 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 - 2-Carboxy-4-dodecanolide 10V, Positive-QTOF	splash10-0007-0960000000-7f3ed15f1d4234b326f4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Carboxy-4-dodecanolide 20V, Positive-QTOF	splash10-002e-6940000000-d1cb0df9ffb216a55497	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Carboxy-4-dodecanolide 40V, Positive-QTOF	splash10-059f-9500000000-61e846546c976fb8f72d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Carboxy-4-dodecanolide 10V, Negative-QTOF	splash10-0005-0930000000-225239f3ebd6daa84f71	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Carboxy-4-dodecanolide 20V, Negative-QTOF	splash10-0002-1900000000-ca3a1529170cc3c3e6a9	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Carboxy-4-dodecanolide 40V, Negative-QTOF	splash10-0zml-7900000000-790253858f2e5de8224c	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Carboxy-4-dodecanolide 10V, Positive-QTOF	splash10-0006-1190000000-4173dfccd532bc269679	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Carboxy-4-dodecanolide 20V, Positive-QTOF	splash10-0a6u-9530000000-01fb334f0e6728f76312	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Carboxy-4-dodecanolide 40V, Positive-QTOF	splash10-0a4l-9200000000-b3aab76ff0cac75d2cfe	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Carboxy-4-dodecanolide 10V, Negative-QTOF	splash10-0006-0290000000-8b4657920e5275fb4028	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Carboxy-4-dodecanolide 20V, Negative-QTOF	splash10-0007-1980000000-e87e963d5e73755a9f6c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Carboxy-4-dodecanolide 40V, Negative-QTOF	splash10-0005-9300000000-f40b1a229260ed189fdf	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB002975

KNApSAcK ID

Not Available

Chemspider ID

35013298

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

85931447

PDB ID

Not Available

ChEBI ID

171710

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 2-Carboxy-4-dodecanolide (HMDB0030987)

MOL for HMDB0030987 (2-Carboxy-4-dodecanolide)

3D MOL for HMDB0030987 (2-Carboxy-4-dodecanolide)

3D SDF for HMDB0030987 (2-Carboxy-4-dodecanolide)

3D-SDF for HMDB0030987 (2-Carboxy-4-dodecanolide)

PDB for HMDB0030987 (2-Carboxy-4-dodecanolide)

3D PDB for HMDB0030987 (2-Carboxy-4-dodecanolide)

SMILES for HMDB0030987 (2-Carboxy-4-dodecanolide)

INCHI for HMDB0030987 (2-Carboxy-4-dodecanolide)

Structure for HMDB0030987 (2-Carboxy-4-dodecanolide)

3D Structure for HMDB0030987 (2-Carboxy-4-dodecanolide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra