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Showing metabocard for Caprylic acid (HMDB0000482)

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enzymes (3)transporters (2) Show 5 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-05-30 20:55:50 UTC
HMDB IDHMDB0000482
Secondary Accession Numbers
  • HMDB00482
  • HMDB0062511
  • HMDB62511
Metabolite Identification
Common NameCaprylic acid
DescriptionCaprylic acid is the common name for the eight-carbon straight-chain fatty acid known by the systematic name octanoic acid. It is found naturally in coconuts and breast milk. It is an oily liquid with a slightly unpleasant rancid taste that is minimally soluble in water. Caprylic acid is used commercially in the production of esters used in perfumery and also in the manufacture of dyes (Wikipedia ). Caprylic acid can be found in numerous foods such as Prunus (Cherry, Plum), pineapple sages, black raspberries, and shallots. Caprylic acid is found to be associated with medium-chain acyl-CoA dehydrogenase deficiency, which is an inborn error of metabolism.
Structure
Data?1676999692
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000482 (Caprylic acid)


  Mrv1652309272007422D          

 10  9  0  0  0  0            999 V2000
   -0.5845   -0.9336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1291   -0.5199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3022   -0.5199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8428   -0.9336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0159   -0.9336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5605   -0.5199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7297   -0.5199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2743   -0.9336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7297    0.3038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4434   -0.9375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  2  0  0  0  0
  7 10  1  0  0  0  0
M  END
Download

3D MOL for HMDB0000482 (Caprylic acid)

HMDB0000482
     RDKit          3D
Caprylic acid
 26 25  0  0  0  0  0  0  0  0999 V2000
   -4.2791   -0.3245    0.4187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1555    0.4935   -0.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8643   -0.1270    0.2550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6519    0.5826   -0.3039 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5677   -0.1542    0.2667 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8486    0.4794   -0.2332 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9933   -0.3033    0.3740 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2956    0.2634   -0.0738 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3543   -0.2600    0.3313 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3789    1.3454   -0.9198 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1311   -1.3797    0.0479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0569   -0.3404    1.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2648    0.0601    0.1647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1991    0.4750   -1.3153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2649    1.5261    0.2011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8432   -1.1626   -0.1275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7866   -0.1414    1.3446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5660    1.6222    0.0280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6150    0.5769   -1.4065 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4604   -1.1969   -0.0526 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4750   -0.1183    1.3702 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8563    0.3215   -1.3417 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8933    1.5501   -0.0294 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9273   -0.1824    1.4662 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8821   -1.3584    0.1124 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7454    1.1969   -1.8579 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  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  4 18  1  0
  4 19  1  0
  5 20  1  0
  5 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
 10 26  1  0
M  END
Download

3D SDF for HMDB0000482 (Caprylic acid)


  Mrv1652309272007422D          

 10  9  0  0  0  0            999 V2000
   -0.5845   -0.9336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1291   -0.5199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3022   -0.5199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8428   -0.9336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0159   -0.9336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5605   -0.5199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7297   -0.5199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2743   -0.9336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7297    0.3038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4434   -0.9375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  2  0  0  0  0
  7 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000482

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10)

> <INCHI_KEY>
WWZKQHOCKIZLMA-UHFFFAOYSA-N

> <FORMULA>
C8H16O2

> <MOLECULAR_WEIGHT>
144.2114

> <EXACT_MASS>
144.115029756

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
17.404174014251353

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
octanoic acid

> <ALOGPS_LOGP>
2.92

> <JCHEM_LOGP>
2.700033457666666

> <ALOGPS_LOGS>
-2.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.192975275996319

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
40.275600000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.07e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
caprylic acid

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0000482 (Caprylic acid)

HMDB0000482
     RDKit          3D
Caprylic acid
 26 25  0  0  0  0  0  0  0  0999 V2000
   -4.2791   -0.3245    0.4187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1555    0.4935   -0.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8643   -0.1270    0.2550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6519    0.5826   -0.3039 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5677   -0.1542    0.2667 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8486    0.4794   -0.2332 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9933   -0.3033    0.3740 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2956    0.2634   -0.0738 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3543   -0.2600    0.3313 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3789    1.3454   -0.9198 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1311   -1.3797    0.0479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0569   -0.3404    1.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2648    0.0601    0.1647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1991    0.4750   -1.3153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2649    1.5261    0.2011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8432   -1.1626   -0.1275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7866   -0.1414    1.3446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5660    1.6222    0.0280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6150    0.5769   -1.4065 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4604   -1.1969   -0.0526 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4750   -0.1183    1.3702 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8563    0.3215   -1.3417 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8933    1.5501   -0.0294 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9273   -0.1824    1.4662 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8821   -1.3584    0.1124 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7454    1.1969   -1.8579 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  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  4 18  1  0
  4 19  1  0
  5 20  1  0
  5 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
 10 26  1  0
M  END
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PDB for HMDB0000482 (Caprylic acid)

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0      -1.091  -1.743   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.241  -0.970   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.431  -0.970   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.573  -1.743   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.763  -1.743   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.913  -0.970   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.095  -0.970   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.245  -1.743   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -5.095   0.567   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -6.428  -1.750   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5    9   10                                                  
CONECT    8    6                                                            
CONECT    9    7                                                            
CONECT   10    7                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END
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3D PDB for HMDB0000482 (Caprylic acid)

COMPND    HMDB0000482
HETATM    1  C1  UNL     1      -4.279  -0.324   0.419  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.155   0.494  -0.224  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.864  -0.127   0.255  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.652   0.583  -0.304  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.568  -0.154   0.267  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.849   0.479  -0.233  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.993  -0.303   0.374  1.00  0.00           C  
HETATM    8  C8  UNL     1       4.296   0.263  -0.074  1.00  0.00           C  
HETATM    9  O1  UNL     1       5.354  -0.260   0.331  1.00  0.00           O  
HETATM   10  O2  UNL     1       4.379   1.345  -0.920  1.00  0.00           O  
HETATM   11  H1  UNL     1      -4.131  -1.380   0.048  1.00  0.00           H  
HETATM   12  H2  UNL     1      -4.057  -0.340   1.505  1.00  0.00           H  
HETATM   13  H3  UNL     1      -5.265   0.060   0.165  1.00  0.00           H  
HETATM   14  H4  UNL     1      -3.199   0.475  -1.315  1.00  0.00           H  
HETATM   15  H5  UNL     1      -3.265   1.526   0.201  1.00  0.00           H  
HETATM   16  H6  UNL     1      -1.843  -1.163  -0.127  1.00  0.00           H  
HETATM   17  H7  UNL     1      -1.787  -0.141   1.345  1.00  0.00           H  
HETATM   18  H8  UNL     1      -0.566   1.622   0.028  1.00  0.00           H  
HETATM   19  H9  UNL     1      -0.615   0.577  -1.406  1.00  0.00           H  
HETATM   20  H10 UNL     1       0.460  -1.197  -0.053  1.00  0.00           H  
HETATM   21  H11 UNL     1       0.475  -0.118   1.370  1.00  0.00           H  
HETATM   22  H12 UNL     1       1.856   0.322  -1.342  1.00  0.00           H  
HETATM   23  H13 UNL     1       1.893   1.550  -0.029  1.00  0.00           H  
HETATM   24  H14 UNL     1       2.927  -0.182   1.466  1.00  0.00           H  
HETATM   25  H15 UNL     1       2.882  -1.358   0.112  1.00  0.00           H  
HETATM   26  H16 UNL     1       4.745   1.197  -1.858  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3   14   15
CONECT    3    4   16   17
CONECT    4    5   18   19
CONECT    5    6   20   21
CONECT    6    7   22   23
CONECT    7    8   24   25
CONECT    8    9    9   10
CONECT   10   26
END
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SMILES for HMDB0000482 (Caprylic acid)

CCCCCCCC(O)=O
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INCHI for HMDB0000482 (Caprylic acid)

InChI=1S/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
1-Heptanecarboxylic acidChEBI
8:0ChEBI
Acide octanoiqueChEBI
Acido octanoicoChEBI
Acidum octanociumChEBI
Acidum octanoicumChEBI
C8:0ChEBI
CH3-[CH2]6-COOHChEBI
KaprylsaeureChEBI
N-Caprylic acidChEBI
N-Octanoic acidChEBI
N-Octoic acidChEBI
N-Octylic acidChEBI
OCTANOIC ACID (caprylIC ACID)ChEBI
OctansaeureChEBI
Octoic acidChEBI
Octylic acidChEBI
OctanoateKegg
1-HeptanecarboxylateGenerator
N-CaprylateGenerator
N-OctanoateGenerator
N-OctoateGenerator
N-OctylateGenerator
OCTANOate (caprylate)Generator
OctoateGenerator
OctylateGenerator
Octanoic acidGenerator
CaprylateGenerator
Emery 657HMDB
Kortacid 0899HMDB
Lunac 8-95HMDB
Lunac 8-98HMDB
Neo-fat 8HMDB
Neo-fat 8SHMDB
Prifac 2901HMDB
Caprylic acid, cadmium saltHMDB
Caprylic acid, cesium saltHMDB
Caprylic acid, manganese saltHMDB
Caprylic acid, nickel(+2) saltHMDB
Caprylic acid, zinc saltHMDB
Caprylic acid, aluminum saltHMDB
Caprylic acid, barium saltHMDB
Caprylic acid, chromium(+2) saltHMDB
Caprylic acid, lead(+2) saltHMDB
Caprylic acid, potassium saltHMDB
Caprylic acid, tin(+2) saltHMDB
Sodium octanoateHMDB
Caprylic acid, 14C-labeledHMDB
Caprylic acid, lithium saltHMDB
Caprylic acid, ruthenium(+3) saltHMDB
Caprylic acid, sodium saltHMDB
Caprylic acid, sodium salt, 11C-labeledHMDB
Caprylic acid, tin saltHMDB
Caprylic acid, zirconium saltHMDB
Sodium caprylateHMDB
Caprylic acid, ammonia saltHMDB
Caprylic acid, calcium saltHMDB
Caprylic acid, cobalt saltHMDB
Caprylic acid, copper saltHMDB
Caprylic acid, copper(+2) saltHMDB
Caprylic acid, iridum(+3) saltHMDB
Caprylic acid, iron(+3) saltHMDB
Caprylic acid, lanthanum(+3) saltHMDB
Caprylic acid, zirconium(+4) saltHMDB
FA(8:0)HMDB
Lithium octanoateHMDB
Chemical FormulaC8H16O2
Average Molecular Weight144.2114
Monoisotopic Molecular Weight144.115029756
IUPAC Nameoctanoic acid
Traditional Namecaprylic acid
CAS Registry Number124-07-2
SMILES
CCCCCCCC(O)=O
InChI Identifier
InChI=1S/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10)
InChI KeyWWZKQHOCKIZLMA-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-chain fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Source
ProcessNot Available
RoleNot Available
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point16.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.79 mg/mLNot Available
LogP3.05HANSCH,C ET AL. (1995)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg139.46130932474
[M-H]-Not Available139.461http://allccs.zhulab.cn/database/detail?ID=AllCCS00000195
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.91 g/LALOGPS
logP2.92ALOGPS
logP2.7ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)5.19ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity40.28 m³·mol⁻¹ChemAxon
Polarizability17.4 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+134.67631661259
DarkChem[M+H]+134.67631661259
DarkChem[M-H]-129.53131661259
DarkChem[M-H]-129.53131661259
AllCCS[M+H]+135.72432859911
AllCCS[M-H]-136.48532859911
DeepCCS[M+H]+145.10830932474
DeepCCS[M-H]-142.15430932474
DeepCCS[M-2H]-178.90130932474
DeepCCS[M+Na]+153.74230932474
AllCCS[M+H]+135.732859911
AllCCS[M+H-H2O]+131.732859911
AllCCS[M+NH4]+139.532859911
AllCCS[M+Na]+140.632859911
AllCCS[M-H]-136.532859911
AllCCS[M+Na-2H]-138.832859911
AllCCS[M+HCOO]-141.332859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.5.71 minutes32390414
Predicted by Siyang on May 30, 202214.0339 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20224.81 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid30.5 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Caprylic acidCCCCCCCC(O)=O2009.7Standard polar33892256
Caprylic acidCCCCCCCC(O)=O1151.2Standard non polar33892256
Caprylic acidCCCCCCCC(O)=O1189.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Caprylic acid,1TMS,isomer #1CCCCCCCC(=O)O[Si](C)(C)C1256.2Semi standard non polar33892256
Caprylic acid,1TBDMS,isomer #1CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C1478.9Semi standard non polar33892256
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Breast Milk
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Sweat
  • Urine
Tissue Locations
  • Epidermis
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.5 (0.0-5.0) uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
 details
BloodDetected and Quantified8.0 (5.0-19.0) uMAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Normal		 details
Breast MilkDetected and Quantified267 +/- 154 uMAdult (>18 years old)Female
Normal		 details
Cerebrospinal Fluid (CSF)Detected and Quantified2.50 +/- 2.50 uMAdult (>18 years old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
SalivaDetected and Quantified0.741 +/- 0.162 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
 details
SalivaDetected and Quantified0.738 +/- 0.193 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
 details
SalivaDetected and Quantified0.218 +/- 0.635 uMAdult (>18 years old)Male
Normal
    • Sugimoto et al. (...
 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
    • Zerihun T. Dame, ...
 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected and Quantified0.629 +/- 0.249 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
 details
SweatDetected but not QuantifiedNot QuantifiedAdult BothNormal details
UrineDetected and Quantified0.0 umol/mmol creatinineChildren (1 - 18 years old)Both
Normal
    • BC Children's Hos...
 details
UrineDetected and Quantified4-10 umol/mmol creatinineChildren (1 - 13 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.39 +/- 0.37 umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified0.15 (0.04-0.22) umol/mmol creatinineNewborn (0-30 days old)Both
Normal
    • Analysis of 40 NI...
 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothAutism details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothCrohns disease details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothUlcerative colitis details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Crohn's disease 		details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative colitis		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBreast cancer details
UrineDetected and Quantified16-410 umol/mmol creatinineChildren (1 - 13 years old)BothMedium Chain Acyl-CoA Dehydrogenase Deficiency details
Associated Disorders and Diseases
Disease References
Autism
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Crohn's disease
  1. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
  2. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
Ulcerative colitis
  1. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
  2. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Perillyl alcohol administration for cancer treatment
  1. Silva CL, Passos M, Camara JS: Solid phase microextraction, mass spectrometry and metabolomic approaches for detection of potential urinary cancer biomarkers--a powerful strategy for breast cancer diagnosis. Talanta. 2012 Jan 30;89:360-8. doi: 10.1016/j.talanta.2011.12.041. Epub 2011 Dec 22. [PubMed:22284503 ]
Medium Chain Acyl-CoA Dehydrogenase Deficiency
  1. Gregersen N, Kolvraa S, Rasmussen K, Mortensen PB, Divry P, David M, Hobolth N: General (medium-chain) acyl-CoA dehydrogenase deficiency (non-ketotic dicarboxylic aciduria): quantitative urinary excretion pattern of 23 biologically significant organic acids in three cases. Clin Chim Acta. 1983 Aug 15;132(2):181-91. [PubMed:6616873 ]
Associated OMIM IDs
DrugBank IDDB04519
Phenol Explorer Compound IDNot Available
FooDB IDFDB003336
KNApSAcK IDC00001231
Chemspider ID370
KEGG Compound IDC06423
BioCyc IDCPD-195
BiGG ID48223
Wikipedia LinkCaprylic_acid
METLIN ID5469
PubChem Compound379
PDB IDNot Available
ChEBI ID28837
Food Biomarker OntologyNot Available
VMH IDOCTA
MarkerDB IDMDB00000171
Good Scents IDNot Available
References
Synthesis ReferenceCaprylic acid. Jpn. Kokai Tokkyo Koho (1983), 4 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69. [PubMed:8412012 ]
  2. Giannakou SA, Dallas PP, Rekkas DM, Choulis NH: In vitro evaluation of nimodipine permeation through human epidermis using response surface methodology. Int J Pharm. 2002 Jul 8;241(1):27-34. [PubMed:12086718 ]
  3. Dieterle F, Muller-Hagedorn S, Liebich HM, Gauglitz G: Urinary nucleosides as potential tumor markers evaluated by learning vector quantization. Artif Intell Med. 2003 Jul;28(3):265-79. [PubMed:12927336 ]
  4. Nair MK, Joy J, Venkitanarayanan KS: Inactivation of Enterobacter sakazakii in reconstituted infant formula by monocaprylin. J Food Prot. 2004 Dec;67(12):2815-9. [PubMed:15633694 ]
  5. Habeeb AF, Francis RD: Preparation of human immunoglobulin by caprylic acid precipitation. Prep Biochem. 1984;14(1):1-17. [PubMed:6718324 ]
  6. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
  11. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

Enzyme Details
1. Peroxisomal carnitine O-octanoyltransferase
General function:
Involved in acyltransferase activity
Specific function:
Beta-oxidation of fatty acids. The highest activity concerns the C6 to C10 chain length substrate. Converts the end product of pristanic acid beta oxidation, 4,8-dimethylnonanoyl-CoA, to its corresponding carnitine ester.
Gene Name:
CROT
Uniprot ID:
Q9UKG9
Molecular weight:
10213.63
Enzyme Details
2. Carnitine O-palmitoyltransferase 2, mitochondrial
General function:
Involved in acyltransferase activity
Specific function:
Not Available
Gene Name:
CPT2
Uniprot ID:
P23786
Molecular weight:
73776.335
Enzyme Details
3. Mitochondrial carnitine/acylcarnitine carrier protein
General function:
Involved in transporter activity
Specific function:
Mediates the transport of acylcarnitines of different length across the mitochondrial inner membrane from the cytosol to the mitochondrial matrix for their oxidation by the mitochondrial fatty acid-oxidation pathway.
Gene Name:
SLC25A20
Uniprot ID:
O43772
Molecular weight:
32943.46

Transporters

Enzyme Details
1. Solute carrier family 22 member 11
General function:
Involved in transporter activity
Specific function:
Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds
Gene Name:
SLC22A11
Uniprot ID:
Q9NSA0
Molecular weight:
59970.9
References
  1. Babu E, Takeda M, Narikawa S, Kobayashi Y, Enomoto A, Tojo A, Cha SH, Sekine T, Sakthisekaran D, Endou H: Role of human organic anion transporter 4 in the transport of ochratoxin A. Biochim Biophys Acta. 2002 Jun 12;1590(1-3):64-75. [PubMed:12063169 ]
Enzyme Details
2. Solute carrier family 22 member 6
General function:
Involved in ion transmembrane transporter activity
Specific function:
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
Molecular weight:
61815.8
References
  1. Jung KY, Takeda M, Kim DK, Tojo A, Narikawa S, Yoo BS, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of ochratoxin A transport by human organic anion transporters. Life Sci. 2001 Sep 21;69(18):2123-35. [PubMed:11669456 ]
  2. Tsuda M, Sekine T, Takeda M, Cha SH, Kanai Y, Kimura M, Endou H: Transport of ochratoxin A by renal multispecific organic anion transporter 1. J Pharmacol Exp Ther. 1999 Jun;289(3):1301-5. [PubMed:10336520 ]