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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

enzymes (2) Show 2 proteins

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2008-10-15 12:12:16 UTC

Update Date

2022-03-07 02:51:02 UTC

HMDB ID

HMDB0010730

Secondary Accession Numbers

HMDB10730

Metabolite Identification

Common Name

3-Oxotetradecanoic acid

Description

3-Oxo-tetradecanoic acid is an intermediate in fatty acid biosynthesis. Specifically, 3-Oxo-tetradecanoic acid is converted from Malonic acid via three enzymes; 3-oxoacyl-[acyl-carrier-protein] synthase, fatty-acid Synthase and beta-ketoacyl -acyl-carrier-protein synthase II. (EC:2.3.1.41, E.C: 2.3.1.85, 2.3.1.179). In humans fatty acids are predominantly formed in the liver and adipose tissue, and mammary glands during lactation.

Structure

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

HMDB0010730
     RDKit          3D
3-Oxotetradecanoic acid
 43 42  0  0  0  0  0  0  0  0999 V2000
    6.1954    0.5342   -0.3178 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9979   -0.2715   -0.7756 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5801   -1.1412    0.4009 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3886   -1.9957    0.0663 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1710   -1.1945   -0.3211 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6949   -0.2734    0.7285 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4911    0.5185    0.2763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6220   -0.4294   -0.0446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8364    0.3382   -0.5001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3102    1.2510    0.5858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5511    1.9918    0.0688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5803    0.9726   -0.2534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7059    0.4745   -1.3665 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4991    0.5517    0.8645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4280   -0.4559    0.3198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3003   -0.9649    1.0643 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3803   -0.8726   -0.9982 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3415    1.3670   -1.0300 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1371   -0.0753   -0.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0553    0.9377    0.6917 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2071    0.4148   -1.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3363   -0.9041   -1.6164 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4266   -1.8363    0.5878 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4631   -0.5238    1.2911 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6653   -2.6303   -0.7982 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1503   -2.6203    0.9268 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3974   -0.6147   -1.2387 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4080   -1.9531   -0.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4710    0.5012    0.9990 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4045   -0.7605    1.6798 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8148    1.1001   -0.6176 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2315    1.2714    1.0522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9147   -0.9809    0.8774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3491   -1.1562   -0.8451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6536   -0.3561   -0.8019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5936    0.9372   -1.4260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6719    0.6130    1.4187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5509    1.9756    0.9024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9017    2.6214    0.9174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2740    2.5903   -0.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8821    0.1241    1.7083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0033    1.4412    1.2871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0203   -0.5169   -1.6923 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
 14 15  1  0
 15 16  2  0
 15 17  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
  9 36  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 14 41  1  0
 14 42  1  0
 17 43  1  0
M  END


  Mrv0541 02241201182D          

 17 16  0  0  0  0            999 V2000
   12.3677   -7.0693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0821   -7.4818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7966   -7.0693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5111   -7.4818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2255   -7.0693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9401   -7.4818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6545   -7.0693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3690   -7.4818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0835   -7.0693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7979   -7.4818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0835   -6.2443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6532   -7.4818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9387   -7.0693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2243   -7.4818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6545   -6.2443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5098   -7.0693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7953   -7.4818    0.0000 C   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
  9  8  1  0  0  0  0
 10  9  2  0  0  0  0
 11  9  1  0  0  0  0
  1 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  7 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0010730

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCCCCCC(=O)CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H26O3/c1-2-3-4-5-6-7-8-9-10-11-13(15)12-14(16)17/h2-12H2,1H3,(H,16,17)

> <INCHI_KEY>
XLKOZYOVXNPWGT-UHFFFAOYSA-N

> <FORMULA>
C14H26O3

> <MOLECULAR_WEIGHT>
242.3544

> <EXACT_MASS>
242.188194698

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
29.635000713083702

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-oxotetradecanoic acid

> <ALOGPS_LOGP>
4.58

> <JCHEM_LOGP>
4.700162086333334

> <ALOGPS_LOGS>
-4.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.053950588383103

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.442108390075651

> <JCHEM_PKA_STRONGEST_BASIC>
-7.537532992598466

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
68.5748

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.71e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-oxotetradecanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0010730
     RDKit          3D
3-Oxotetradecanoic acid
 43 42  0  0  0  0  0  0  0  0999 V2000
    6.1954    0.5342   -0.3178 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9979   -0.2715   -0.7756 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5801   -1.1412    0.4009 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3886   -1.9957    0.0663 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1710   -1.1945   -0.3211 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6949   -0.2734    0.7285 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4911    0.5185    0.2763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6220   -0.4294   -0.0446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8364    0.3382   -0.5001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3102    1.2510    0.5858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5511    1.9918    0.0688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5803    0.9726   -0.2534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7059    0.4745   -1.3665 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4991    0.5517    0.8645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4280   -0.4559    0.3198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3003   -0.9649    1.0643 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3803   -0.8726   -0.9982 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3415    1.3670   -1.0300 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1371   -0.0753   -0.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0553    0.9377    0.6917 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2071    0.4148   -1.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3363   -0.9041   -1.6164 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4266   -1.8363    0.5878 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4631   -0.5238    1.2911 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6653   -2.6303   -0.7982 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1503   -2.6203    0.9268 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3974   -0.6147   -1.2387 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4080   -1.9531   -0.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4710    0.5012    0.9990 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4045   -0.7605    1.6798 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8148    1.1001   -0.6176 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2315    1.2714    1.0522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9147   -0.9809    0.8774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3491   -1.1562   -0.8451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6536   -0.3561   -0.8019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5936    0.9372   -1.4260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6719    0.6130    1.4187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5509    1.9756    0.9024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9017    2.6214    0.9174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2740    2.5903   -0.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8821    0.1241    1.7083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0033    1.4412    1.2871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0203   -0.5169   -1.6923 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
 14 15  1  0
 15 16  2  0
 15 17  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
  9 36  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 14 41  1  0
 14 42  1  0
 17 43  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      23.086 -13.196   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      24.420 -13.966   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      25.754 -13.196   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      27.087 -13.966   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      28.421 -13.196   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      29.755 -13.966   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      31.088 -13.196   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      32.422 -13.966   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      33.756 -13.196   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      35.089 -13.966   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      33.756 -11.656   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      21.753 -13.966   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      20.419 -13.196   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      19.085 -13.966   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      31.088 -11.656   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      17.752 -13.196   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      16.418 -13.966   0.000  0.00  0.00           C+0
CONECT    1    2   12                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   15                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    1   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   16                                                       
CONECT   15    7                                                            
CONECT   16   14   17                                                       
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   32    0
END

COMPND    HMDB0010730
HETATM    1  C1  UNL     1       6.195   0.534  -0.318  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.998  -0.271  -0.776  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.580  -1.141   0.401  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.389  -1.996   0.066  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.171  -1.195  -0.321  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.695  -0.273   0.728  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.491   0.519   0.276  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.622  -0.429  -0.045  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.836   0.338  -0.500  1.00  0.00           C  
HETATM   10  C10 UNL     1      -2.310   1.251   0.586  1.00  0.00           C  
HETATM   11  C11 UNL     1      -3.551   1.992   0.069  1.00  0.00           C  
HETATM   12  C12 UNL     1      -4.580   0.973  -0.253  1.00  0.00           C  
HETATM   13  O1  UNL     1      -4.706   0.474  -1.367  1.00  0.00           O  
HETATM   14  C13 UNL     1      -5.499   0.552   0.865  1.00  0.00           C  
HETATM   15  C14 UNL     1      -6.428  -0.456   0.320  1.00  0.00           C  
HETATM   16  O2  UNL     1      -7.300  -0.965   1.064  1.00  0.00           O  
HETATM   17  O3  UNL     1      -6.380  -0.873  -0.998  1.00  0.00           O  
HETATM   18  H1  UNL     1       6.342   1.367  -1.030  1.00  0.00           H  
HETATM   19  H2  UNL     1       7.137  -0.075  -0.322  1.00  0.00           H  
HETATM   20  H3  UNL     1       6.055   0.938   0.692  1.00  0.00           H  
HETATM   21  H4  UNL     1       4.207   0.415  -1.090  1.00  0.00           H  
HETATM   22  H5  UNL     1       5.336  -0.904  -1.616  1.00  0.00           H  
HETATM   23  H6  UNL     1       5.427  -1.836   0.588  1.00  0.00           H  
HETATM   24  H7  UNL     1       4.463  -0.524   1.291  1.00  0.00           H  
HETATM   25  H8  UNL     1       3.665  -2.630  -0.798  1.00  0.00           H  
HETATM   26  H9  UNL     1       3.150  -2.620   0.927  1.00  0.00           H  
HETATM   27  H10 UNL     1       2.397  -0.615  -1.239  1.00  0.00           H  
HETATM   28  H11 UNL     1       1.408  -1.953  -0.610  1.00  0.00           H  
HETATM   29  H12 UNL     1       2.471   0.501   0.999  1.00  0.00           H  
HETATM   30  H13 UNL     1       1.405  -0.760   1.680  1.00  0.00           H  
HETATM   31  H14 UNL     1       0.815   1.100  -0.618  1.00  0.00           H  
HETATM   32  H15 UNL     1       0.232   1.271   1.052  1.00  0.00           H  
HETATM   33  H16 UNL     1      -0.915  -0.981   0.877  1.00  0.00           H  
HETATM   34  H17 UNL     1      -0.349  -1.156  -0.845  1.00  0.00           H  
HETATM   35  H18 UNL     1      -2.654  -0.356  -0.802  1.00  0.00           H  
HETATM   36  H19 UNL     1      -1.594   0.937  -1.426  1.00  0.00           H  
HETATM   37  H20 UNL     1      -2.672   0.613   1.419  1.00  0.00           H  
HETATM   38  H21 UNL     1      -1.551   1.976   0.902  1.00  0.00           H  
HETATM   39  H22 UNL     1      -3.902   2.621   0.917  1.00  0.00           H  
HETATM   40  H23 UNL     1      -3.274   2.590  -0.815  1.00  0.00           H  
HETATM   41  H24 UNL     1      -4.882   0.124   1.708  1.00  0.00           H  
HETATM   42  H25 UNL     1      -6.003   1.441   1.287  1.00  0.00           H  
HETATM   43  H26 UNL     1      -7.020  -0.517  -1.692  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   35   36
CONECT   10   11   37   38
CONECT   11   12   39   40
CONECT   12   13   13   14
CONECT   14   15   41   42
CONECT   15   16   16   17
CONECT   17   43
END

HMDB0010730
     RDKit          3D
3-Oxotetradecanoic acid
 43 42  0  0  0  0  0  0  0  0999 V2000
    6.1954    0.5342   -0.3178 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9979   -0.2715   -0.7756 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5801   -1.1412    0.4009 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3886   -1.9957    0.0663 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1710   -1.1945   -0.3211 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6949   -0.2734    0.7285 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4911    0.5185    0.2763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6220   -0.4294   -0.0446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8364    0.3382   -0.5001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3102    1.2510    0.5858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5511    1.9918    0.0688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5803    0.9726   -0.2534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7059    0.4745   -1.3665 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4991    0.5517    0.8645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4280   -0.4559    0.3198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3003   -0.9649    1.0643 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3803   -0.8726   -0.9982 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3415    1.3670   -1.0300 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1371   -0.0753   -0.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0553    0.9377    0.6917 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2071    0.4148   -1.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3363   -0.9041   -1.6164 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4266   -1.8363    0.5878 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4631   -0.5238    1.2911 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6653   -2.6303   -0.7982 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1503   -2.6203    0.9268 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3974   -0.6147   -1.2387 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4080   -1.9531   -0.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4710    0.5012    0.9990 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4045   -0.7605    1.6798 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8148    1.1001   -0.6176 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2315    1.2714    1.0522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9147   -0.9809    0.8774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3491   -1.1562   -0.8451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6536   -0.3561   -0.8019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5936    0.9372   -1.4260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6719    0.6130    1.4187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5509    1.9756    0.9024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9017    2.6214    0.9174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2740    2.5903   -0.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8821    0.1241    1.7083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0033    1.4412    1.2871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0203   -0.5169   -1.6923 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
 14 15  1  0
 15 16  2  0
 15 17  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
  9 36  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 14 41  1  0
 14 42  1  0
 17 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Oxotetradecanoate	Generator
3-Oxomyristic acid	ChEBI
3-Oxomyristate	Generator
3-oxo-Tetradecanoate	HMDB
3-oxo-Tetradecanoic acid	HMDB

Chemical Formula

C₁₄H₂₆O₃

Average Molecular Weight

242.3544

Monoisotopic Molecular Weight

242.188194698

IUPAC Name

3-oxotetradecanoic acid

Traditional Name

3-oxotetradecanoic acid

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCC(=O)CC(O)=O

InChI Identifier

InChI=1S/C14H26O3/c1-2-3-4-5-6-7-8-9-10-11-13(15)12-14(16)17/h2-12H2,1H3,(H,16,17)

InChI Key

XLKOZYOVXNPWGT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

Long-chain fatty acid
Beta-keto acid
Keto fatty acid
Beta-hydroxy ketone
Keto acid
1,3-dicarbonyl compound
Ketone
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

long-chain fatty acid (CHEBI:37270 )
3-oxo monocarboxylic acid (CHEBI:37270 )
oxo fatty acid (CHEBI:37270 )
Oxo fatty acids (LMFA01060099 )

Ontology

Not Available

Physical Properties

State

Solid

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	0.0047 g/L	ALOGPS
logP	4.58	ALOGPS
logP	4.7	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	4.44	ChemAxon
pKa (Strongest Basic)	-7.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	68.57 m³·mol⁻¹	ChemAxon
Polarizability	29.64 Å³	ChemAxon
Number of Rings	0	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]+	162.639	31661259
DarkChem	[M-H]-	161.217	31661259
DeepCCS	[M+H]+	162.693	30932474
DeepCCS	[M-H]-	158.67	30932474
DeepCCS	[M-2H]-	195.937	30932474
DeepCCS	[M+Na]+	171.728	30932474
AllCCS	[M+H]+	164.1	32859911
AllCCS	[M+H-H2O]+	160.8	32859911
AllCCS	[M+NH4]+	167.2	32859911
AllCCS	[M+Na]+	168.1	32859911
AllCCS	[M-H]-	164.4	32859911
AllCCS	[M+Na-2H]-	165.4	32859911
AllCCS	[M+HCOO]-	166.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Oxotetradecanoic acid	CCCCCCCCCCCC(=O)CC(O)=O	3022.7	Standard polar	33892256
3-Oxotetradecanoic acid	CCCCCCCCCCCC(=O)CC(O)=O	1807.8	Standard non polar	33892256
3-Oxotetradecanoic acid	CCCCCCCCCCCC(=O)CC(O)=O	1904.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Oxotetradecanoic acid,1TMS,isomer #1	CCCCCCCCCCCC(=O)CC(=O)O[Si](C)(C)C	1950.7	Semi standard non polar	33892256
3-Oxotetradecanoic acid,1TMS,isomer #2	CCCCCCCCCCCC(=CC(=O)O)O[Si](C)(C)C	2082.1	Semi standard non polar	33892256
3-Oxotetradecanoic acid,1TMS,isomer #3	CCCCCCCCCCC=C(CC(=O)O)O[Si](C)(C)C	2029.4	Semi standard non polar	33892256
3-Oxotetradecanoic acid,2TMS,isomer #1	CCCCCCCCCCCC(=CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2107.6	Semi standard non polar	33892256
3-Oxotetradecanoic acid,2TMS,isomer #1	CCCCCCCCCCCC(=CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2102.4	Standard non polar	33892256
3-Oxotetradecanoic acid,2TMS,isomer #1	CCCCCCCCCCCC(=CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2073.8	Standard polar	33892256
3-Oxotetradecanoic acid,2TMS,isomer #2	CCCCCCCCCCC=C(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2095.3	Semi standard non polar	33892256
3-Oxotetradecanoic acid,2TMS,isomer #2	CCCCCCCCCCC=C(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2103.8	Standard non polar	33892256
3-Oxotetradecanoic acid,2TMS,isomer #2	CCCCCCCCCCC=C(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2096.0	Standard polar	33892256
3-Oxotetradecanoic acid,1TBDMS,isomer #1	CCCCCCCCCCCC(=O)CC(=O)O[Si](C)(C)C(C)(C)C	2189.9	Semi standard non polar	33892256
3-Oxotetradecanoic acid,1TBDMS,isomer #2	CCCCCCCCCCCC(=CC(=O)O)O[Si](C)(C)C(C)(C)C	2325.9	Semi standard non polar	33892256
3-Oxotetradecanoic acid,1TBDMS,isomer #3	CCCCCCCCCCC=C(CC(=O)O)O[Si](C)(C)C(C)(C)C	2278.8	Semi standard non polar	33892256
3-Oxotetradecanoic acid,2TBDMS,isomer #1	CCCCCCCCCCCC(=CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2583.2	Semi standard non polar	33892256
3-Oxotetradecanoic acid,2TBDMS,isomer #1	CCCCCCCCCCCC(=CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2464.5	Standard non polar	33892256
3-Oxotetradecanoic acid,2TBDMS,isomer #1	CCCCCCCCCCCC(=CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2356.8	Standard polar	33892256
3-Oxotetradecanoic acid,2TBDMS,isomer #2	CCCCCCCCCCC=C(CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2556.9	Semi standard non polar	33892256
3-Oxotetradecanoic acid,2TBDMS,isomer #2	CCCCCCCCCCC=C(CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2472.1	Standard non polar	33892256
3-Oxotetradecanoic acid,2TBDMS,isomer #2	CCCCCCCCCCC=C(CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2367.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Oxotetradecanoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-9300000000-caec0675bb7cc4bf645e	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Oxotetradecanoic acid GC-MS (1 TMS) - 70eV, Positive	splash10-05bu-9240000000-9f5c74b9b22322bac095	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Oxotetradecanoic 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 - 3-Oxotetradecanoic acid 10V, Positive-QTOF	splash10-002f-0290000000-8e607f12b728cd17d0eb	2016-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxotetradecanoic acid 20V, Positive-QTOF	splash10-004m-4920000000-4703c7195a11feeb2b5a	2016-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxotetradecanoic acid 40V, Positive-QTOF	splash10-052f-9300000000-a7e2659c4534794225d0	2016-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxotetradecanoic acid 10V, Negative-QTOF	splash10-0007-1890000000-62a40531fb987abfd8b6	2016-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxotetradecanoic acid 20V, Negative-QTOF	splash10-0002-3910000000-d4867d427aeab7a02553	2016-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxotetradecanoic acid 40V, Negative-QTOF	splash10-0a4i-9300000000-4b25931f846416282cca	2016-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxotetradecanoic acid 10V, Positive-QTOF	splash10-0006-9670000000-20164b0847d143f44c74	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxotetradecanoic acid 20V, Positive-QTOF	splash10-05nb-9200000000-5468639cd8cec19d4dcd	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxotetradecanoic acid 40V, Positive-QTOF	splash10-0a5d-9000000000-ed47cbde55f8e1b78e23	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxotetradecanoic acid 10V, Negative-QTOF	splash10-052f-6090000000-a84a5a93ec99d19f1719	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxotetradecanoic acid 20V, Negative-QTOF	splash10-0a4i-9010000000-6a10d917408e88ed0e4b	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxotetradecanoic acid 40V, Negative-QTOF	splash10-0006-9000000000-f1c0182976e7a431dba9	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Feces

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Fatty Acid Biosynthesis		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Iron deficiency	26848182	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ulcerative colitis	26848182	details

Associated Disorders and Diseases

Disease References

Iron deficiency
Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]
Ulcerative colitis
Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB027877

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

Enzyme Details

1. Fatty acid synthase

General function:: Involved in transferase activity
Specific function:: Fatty acid synthetase catalyzes the formation of long-chain fatty acids from acetyl-CoA, malonyl-CoA and NADPH. This multifunctional protein has 7 catalytic activities and an acyl carrier protein.
Gene Name:: FASN
Uniprot ID:: P49327
Molecular weight:: 273424.06

Enzyme Details

2. 3-oxoacyl-[acyl-carrier-protein] synthase, mitochondrial

General function:: Involved in catalytic activity
Specific function:: May play a role in the biosynthesis of lipoic acid as well as longer chain fatty acids required for optimal mitochondrial function.
Gene Name:: OXSM
Uniprot ID:: Q9NWU1
Molecular weight:: 40034.535

Showing metabocard for 3-Oxotetradecanoic acid (HMDB0010730)

MOL for HMDB0010730 (3-Oxotetradecanoic acid)

3D MOL for HMDB0010730 (3-Oxotetradecanoic acid)

3D SDF for HMDB0010730 (3-Oxotetradecanoic acid)

3D-SDF for HMDB0010730 (3-Oxotetradecanoic acid)

PDB for HMDB0010730 (3-Oxotetradecanoic acid)

3D PDB for HMDB0010730 (3-Oxotetradecanoic acid)

SMILES for HMDB0010730 (3-Oxotetradecanoic acid)

INCHI for HMDB0010730 (3-Oxotetradecanoic acid)

Structure for HMDB0010730 (3-Oxotetradecanoic acid)

3D Structure for HMDB0010730 (3-Oxotetradecanoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes