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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:40:12 UTC

Update Date

2022-03-07 02:52:46 UTC

HMDB ID

HMDB0030984

Secondary Accession Numbers

HMDB30984

Metabolite Identification

Common Name

5-Hexyltetrahydro-2-oxo-3-furancarboxylic acid

Description

5-Hexyltetrahydro-2-oxo-3-furancarboxylic acid, also known as 2-carboxy-4-decanolide or a-carboxy-g-decalactone, 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 a significant number of articles have been published on 5-Hexyltetrahydro-2-oxo-3-furancarboxylic acid.

Structure

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

HMDB0030984
     RDKit          3D
5-Hexyltetrahydro-2-oxo-3-furancarboxylic acid
 33 33  0  0  0  0  0  0  0  0999 V2000
   -4.3664    0.8415    0.0465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9653   -0.5203    0.5987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4506   -0.5920    0.5937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9931   -0.4257   -0.8213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4981   -0.4754   -0.9841 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2168    0.5888   -0.2147 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7054    0.4373   -0.4563 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2185   -0.8963   -0.0152 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4619   -0.5013    0.7823 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5582   -0.1134   -0.1393 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6469   -0.7395   -0.1350 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4245    0.9408   -1.0283 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9638    0.7702    1.3998 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0934    1.1257    2.5973 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3482    1.4186    0.3366 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3654    1.1452    0.4379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4545    0.7821   -1.0523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6170    1.6221    0.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3183   -1.2779   -0.1372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3908   -0.6937    1.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1716   -1.5917    0.9915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0972    0.2278    1.2495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4382    0.4913   -1.2463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4079   -1.2712   -1.4214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0816   -1.4502   -0.7060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2849   -0.3079   -2.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0443    1.6210   -0.5568 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0706    0.5003    0.8844 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9474    0.6024   -1.5466 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5177   -1.3502    0.7064 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5046   -1.5634   -0.8361 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7510   -1.2393    1.5189 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5162    1.8942   -0.6529 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  2  0
 10 12  1  0
  9 13  1  0
 13 14  2  0
 13 15  1  0
 15  7  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
 12 33  1  0
M  END


  Mrv0541 05061305382D          

 15 15  0  0  0  0            999 V2000
    2.4489   -3.3644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1634   -2.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8779   -3.3644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5923   -2.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3068   -3.3644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0213   -2.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4894   -3.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7357   -3.3644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0414   -3.6419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8619   -3.5557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6289   -4.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1975   -2.8020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3468   -4.2231    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9645   -5.1100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8220   -4.1848    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
  8  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  7  1  0  0  0  0
 10  9  1  0  0  0  0
 11  9  1  0  0  0  0
 12 10  2  0  0  0  0
 13 10  1  0  0  0  0
 14 11  2  0  0  0  0
 15  8  1  0  0  0  0
 15 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030984

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCC1CC(C(O)=O)C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C11H18O4/c1-2-3-4-5-6-8-7-9(10(12)13)11(14)15-8/h8-9H,2-7H2,1H3,(H,12,13)

> <INCHI_KEY>
ZHNHBUOFMLNZNN-UHFFFAOYSA-N

> <FORMULA>
C11H18O4

> <MOLECULAR_WEIGHT>
214.2582

> <EXACT_MASS>
214.120509064

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
23.23819868714373

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.56

> <JCHEM_LOGP>
2.601602262666666

> <ALOGPS_LOGS>
-2.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.093556602172378

> <JCHEM_PKA_STRONGEST_BASIC>
-7.196951635837928

> <JCHEM_POLAR_SURFACE_AREA>
63.599999999999994

> <JCHEM_REFRACTIVITY>
53.94660000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.43e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030984
     RDKit          3D
5-Hexyltetrahydro-2-oxo-3-furancarboxylic acid
 33 33  0  0  0  0  0  0  0  0999 V2000
   -4.3664    0.8415    0.0465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9653   -0.5203    0.5987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4506   -0.5920    0.5937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9931   -0.4257   -0.8213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4981   -0.4754   -0.9841 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2168    0.5888   -0.2147 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7054    0.4373   -0.4563 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2185   -0.8963   -0.0152 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4619   -0.5013    0.7823 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5582   -0.1134   -0.1393 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6469   -0.7395   -0.1350 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4245    0.9408   -1.0283 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9638    0.7702    1.3998 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0934    1.1257    2.5973 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3482    1.4186    0.3366 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3654    1.1452    0.4379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4545    0.7821   -1.0523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6170    1.6221    0.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3183   -1.2779   -0.1372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3908   -0.6937    1.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1716   -1.5917    0.9915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0972    0.2278    1.2495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4382    0.4913   -1.2463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4079   -1.2712   -1.4214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0816   -1.4502   -0.7060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2849   -0.3079   -2.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0443    1.6210   -0.5568 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0706    0.5003    0.8844 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9474    0.6024   -1.5466 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5177   -1.3502    0.7064 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5046   -1.5634   -0.8361 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7510   -1.2393    1.5189 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5162    1.8942   -0.6529 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  2  0
 10 12  1  0
  9 13  1  0
 13 14  2  0
 13 15  1  0
 15  7  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
 12 33  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       4.571  -6.280   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.905  -5.510   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.239  -6.280   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.572  -5.510   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.906  -6.280   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.240  -5.510   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.980  -5.654   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.573  -6.280   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.011  -6.798   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      16.542  -6.637   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.241  -8.132   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      17.169  -5.230   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      17.447  -7.883   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      14.867  -9.539   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      12.734  -7.812   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    8                                                       
CONECT    7    8    9                                                       
CONECT    8    6    7   15                                                  
CONECT    9    7   10   11                                                  
CONECT   10    9   12   13                                                  
CONECT   11    9   14   15                                                  
CONECT   12   10                                                            
CONECT   13   10                                                            
CONECT   14   11                                                            
CONECT   15    8   11                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0030984
HETATM    1  C1  UNL     1      -4.366   0.841   0.046  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.965  -0.520   0.599  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.451  -0.592   0.594  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.993  -0.426  -0.821  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.498  -0.475  -0.984  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.217   0.589  -0.215  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.705   0.437  -0.456  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.218  -0.896  -0.015  1.00  0.00           C  
HETATM    9  C9  UNL     1       3.462  -0.501   0.782  1.00  0.00           C  
HETATM   10  C10 UNL     1       4.558  -0.113  -0.139  1.00  0.00           C  
HETATM   11  O1  UNL     1       5.647  -0.740  -0.135  1.00  0.00           O  
HETATM   12  O2  UNL     1       4.425   0.941  -1.028  1.00  0.00           O  
HETATM   13  C11 UNL     1       2.964   0.770   1.400  1.00  0.00           C  
HETATM   14  O3  UNL     1       3.093   1.126   2.597  1.00  0.00           O  
HETATM   15  O4  UNL     1       2.348   1.419   0.337  1.00  0.00           O  
HETATM   16  H1  UNL     1      -5.365   1.145   0.438  1.00  0.00           H  
HETATM   17  H2  UNL     1      -4.455   0.782  -1.052  1.00  0.00           H  
HETATM   18  H3  UNL     1      -3.617   1.622   0.283  1.00  0.00           H  
HETATM   19  H4  UNL     1      -4.318  -1.278  -0.137  1.00  0.00           H  
HETATM   20  H5  UNL     1      -4.391  -0.694   1.597  1.00  0.00           H  
HETATM   21  H6  UNL     1      -2.172  -1.592   0.991  1.00  0.00           H  
HETATM   22  H7  UNL     1      -2.097   0.228   1.249  1.00  0.00           H  
HETATM   23  H8  UNL     1      -2.438   0.491  -1.246  1.00  0.00           H  
HETATM   24  H9  UNL     1      -2.408  -1.271  -1.421  1.00  0.00           H  
HETATM   25  H10 UNL     1      -0.082  -1.450  -0.706  1.00  0.00           H  
HETATM   26  H11 UNL     1      -0.285  -0.308  -2.063  1.00  0.00           H  
HETATM   27  H12 UNL     1      -0.044   1.621  -0.557  1.00  0.00           H  
HETATM   28  H13 UNL     1       0.071   0.500   0.884  1.00  0.00           H  
HETATM   29  H14 UNL     1       1.947   0.602  -1.547  1.00  0.00           H  
HETATM   30  H15 UNL     1       1.518  -1.350   0.706  1.00  0.00           H  
HETATM   31  H16 UNL     1       2.505  -1.563  -0.836  1.00  0.00           H  
HETATM   32  H17 UNL     1       3.751  -1.239   1.519  1.00  0.00           H  
HETATM   33  H18 UNL     1       4.516   1.894  -0.653  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3   19   20
CONECT    3    4   21   22
CONECT    4    5   23   24
CONECT    5    6   25   26
CONECT    6    7   27   28
CONECT    7    8   15   29
CONECT    8    9   30   31
CONECT    9   10   13   32
CONECT   10   11   11   12
CONECT   12   33
CONECT   13   14   14   15
END

HMDB0030984
     RDKit          3D
5-Hexyltetrahydro-2-oxo-3-furancarboxylic acid
 33 33  0  0  0  0  0  0  0  0999 V2000
   -4.3664    0.8415    0.0465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9653   -0.5203    0.5987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4506   -0.5920    0.5937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9931   -0.4257   -0.8213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4981   -0.4754   -0.9841 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2168    0.5888   -0.2147 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7054    0.4373   -0.4563 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2185   -0.8963   -0.0152 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4619   -0.5013    0.7823 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5582   -0.1134   -0.1393 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6469   -0.7395   -0.1350 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4245    0.9408   -1.0283 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9638    0.7702    1.3998 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0934    1.1257    2.5973 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3482    1.4186    0.3366 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3654    1.1452    0.4379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4545    0.7821   -1.0523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6170    1.6221    0.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3183   -1.2779   -0.1372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3908   -0.6937    1.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1716   -1.5917    0.9915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0972    0.2278    1.2495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4382    0.4913   -1.2463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4079   -1.2712   -1.4214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0816   -1.4502   -0.7060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2849   -0.3079   -2.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0443    1.6210   -0.5568 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0706    0.5003    0.8844 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9474    0.6024   -1.5466 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5177   -1.3502    0.7064 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5046   -1.5634   -0.8361 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7510   -1.2393    1.5189 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5162    1.8942   -0.6529 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  2  0
 10 12  1  0
  9 13  1  0
 13 14  2  0
 13 15  1  0
 15  7  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
 12 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5-Hexyltetrahydro-2-oxo-3-furancarboxylate	Generator
2-Carboxy-4-decanolide	HMDB
a-Carboxy-g-decalactone	HMDB
5-Hexyl-2-oxooxolane-3-carboxylate	HMDB

Chemical Formula

C₁₁H₁₈O₄

Average Molecular Weight

214.2582

Monoisotopic Molecular Weight

214.120509064

IUPAC Name

5-hexyl-2-oxooxolane-3-carboxylic acid

Traditional Name

5-hexyl-2-oxooxolane-3-carboxylic acid

CAS Registry Number

Not Available

SMILES

CCCCCCC1CC(C(O)=O)C(=O)O1

InChI Identifier

InChI=1S/C11H18O4/c1-2-3-4-5-6-8-7-9(10(12)13)11(14)15-8/h8-9H,2-7H2,1H3,(H,12,13)

InChI Key

ZHNHBUOFMLNZNN-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: HMDB0030984)
Cell membrane (HMDB: HMDB0030984)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030984)

Source

Endogenous

Endogenous (HMDB: HMDB0030984)

Animal

Animal (HMDB: HMDB0030984)

Exogenous

Food

Food (HMDB: HMDB0030984)

Milk and milk product

Milk and milk products (FooDB: FOOD00863)

Exogenous (HMDB: HMDB0030984)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	60.5 - 62.5 °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	0.94 g/L	ALOGPS
logP	2.56	ALOGPS
logP	2.6	ChemAxon
logS	-2.4	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	6	ChemAxon
Refractivity	53.95 m³·mol⁻¹	ChemAxon
Polarizability	23.24 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]+	151.84	31661259
DarkChem	[M-H]-	149.636	31661259
DeepCCS	[M+H]+	156.602	30932474
DeepCCS	[M-H]-	152.605	30932474
DeepCCS	[M-2H]-	189.708	30932474
DeepCCS	[M+Na]+	165.464	30932474
AllCCS	[M+H]+	151.3	32859911
AllCCS	[M+H-H2O]+	147.4	32859911
AllCCS	[M+NH4]+	154.9	32859911
AllCCS	[M+Na]+	155.9	32859911
AllCCS	[M-H]-	153.0	32859911
AllCCS	[M+Na-2H]-	153.7	32859911
AllCCS	[M+HCOO]-	154.5	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.	6.52 minutes	32390414
Predicted by Siyang on May 30, 2022	14.4393 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.28 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2239.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	398.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	159.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	231.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	353.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	638.7 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	680.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	85.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1241.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	454.8 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	1473.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	410.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	406.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	468.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	390.8 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	81.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-Hexyltetrahydro-2-oxo-3-furancarboxylic acid	CCCCCCC1CC(C(O)=O)C(=O)O1	2851.7	Standard polar	33892256
5-Hexyltetrahydro-2-oxo-3-furancarboxylic acid	CCCCCCC1CC(C(O)=O)C(=O)O1	1709.9	Standard non polar	33892256
5-Hexyltetrahydro-2-oxo-3-furancarboxylic acid	CCCCCCC1CC(C(O)=O)C(=O)O1	1847.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-Hexyltetrahydro-2-oxo-3-furancarboxylic acid,1TMS,isomer #1	CCCCCCC1CC(C(=O)O[Si](C)(C)C)C(=O)O1	1754.6	Semi standard non polar	33892256
5-Hexyltetrahydro-2-oxo-3-furancarboxylic acid,1TBDMS,isomer #1	CCCCCCC1CC(C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O1	2014.8	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 - 5-Hexyltetrahydro-2-oxo-3-furancarboxylic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0603-9300000000-9e538f47f6d54c95e17b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hexyltetrahydro-2-oxo-3-furancarboxylic acid GC-MS (1 TMS) - 70eV, Positive	splash10-00dr-9120000000-870d16dee2e57fa9f894	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hexyltetrahydro-2-oxo-3-furancarboxylic 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 - 5-Hexyltetrahydro-2-oxo-3-furancarboxylic acid 10V, Positive-QTOF	splash10-014i-0930000000-bddfe7772595bfb236b2	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hexyltetrahydro-2-oxo-3-furancarboxylic acid 20V, Positive-QTOF	splash10-014j-6920000000-5f3a701f6c1cc23f59a7	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hexyltetrahydro-2-oxo-3-furancarboxylic acid 40V, Positive-QTOF	splash10-052f-9300000000-46002dbd3ae5ad511f15	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hexyltetrahydro-2-oxo-3-furancarboxylic acid 10V, Negative-QTOF	splash10-02t9-0930000000-06985db2b304b73a6b0c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hexyltetrahydro-2-oxo-3-furancarboxylic acid 20V, Negative-QTOF	splash10-014i-2900000000-273155171e9a79f5abc5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hexyltetrahydro-2-oxo-3-furancarboxylic acid 40V, Negative-QTOF	splash10-00fu-9700000000-5f173947c3bee7a7b249	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hexyltetrahydro-2-oxo-3-furancarboxylic acid 10V, Negative-QTOF	splash10-03di-0590000000-0aeb9b818982b0e1c23b	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hexyltetrahydro-2-oxo-3-furancarboxylic acid 20V, Negative-QTOF	splash10-03xr-2980000000-b1b1f240dce6f79b2de1	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hexyltetrahydro-2-oxo-3-furancarboxylic acid 40V, Negative-QTOF	splash10-0005-9300000000-0049ea5cf4702f2f815f	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hexyltetrahydro-2-oxo-3-furancarboxylic acid 10V, Positive-QTOF	splash10-014i-4290000000-d2901598b49c489b8679	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hexyltetrahydro-2-oxo-3-furancarboxylic acid 20V, Positive-QTOF	splash10-052f-9500000000-4191de2bd3b6fc48c2a4	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hexyltetrahydro-2-oxo-3-furancarboxylic acid 40V, Positive-QTOF	splash10-052f-9200000000-978812a72a206fb26590	2021-09-25	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

FDB002972

KNApSAcK ID

Not Available

Chemspider ID

8551389

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10375946

PDB ID

Not Available

ChEBI ID

166552

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 5-Hexyltetrahydro-2-oxo-3-furancarboxylic acid (HMDB0030984)

MOL for HMDB0030984 (5-Hexyltetrahydro-2-oxo-3-furancarboxylic acid)

3D MOL for HMDB0030984 (5-Hexyltetrahydro-2-oxo-3-furancarboxylic acid)

3D SDF for HMDB0030984 (5-Hexyltetrahydro-2-oxo-3-furancarboxylic acid)

3D-SDF for HMDB0030984 (5-Hexyltetrahydro-2-oxo-3-furancarboxylic acid)

PDB for HMDB0030984 (5-Hexyltetrahydro-2-oxo-3-furancarboxylic acid)

3D PDB for HMDB0030984 (5-Hexyltetrahydro-2-oxo-3-furancarboxylic acid)

SMILES for HMDB0030984 (5-Hexyltetrahydro-2-oxo-3-furancarboxylic acid)

INCHI for HMDB0030984 (5-Hexyltetrahydro-2-oxo-3-furancarboxylic acid)

Structure for HMDB0030984 (5-Hexyltetrahydro-2-oxo-3-furancarboxylic acid)

3D Structure for HMDB0030984 (5-Hexyltetrahydro-2-oxo-3-furancarboxylic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra