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Showing metabocard for Caproic acid (HMDB0000535)

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enzymes (10) Show 10 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-05-30 20:55:51 UTC
HMDB IDHMDB0000535
Secondary Accession Numbers
  • HMDB00535
  • HMDB0061883
  • HMDB61883
Metabolite Identification
Common NameCaproic acid
DescriptionCaproic acid, also known as hexanoic acid or C6:0, is a medium-chain fatty acid. Medium-chain fatty acids (MCFA) are fatty acids with aliphatic tails of 6 to 12 carbons, which can form medium-chain triglycerides. Caproic acid is a colourless oily liquid that smells like cheese with an overlying waxy or barnyard odor like that of goats or other barnyard animals. Its name comes from the Latin word capra, meaning "goat". Two other fatty acids are named after goats: caprylic acid (C8) and capric acid (C10). Along with caproic acid, they account for 15% of the fat in goat's milk. Caproic acid is a fatty acid found naturally in various animal fats and oils. While generally more abundant in animals, caproic acid is found in all organisms ranging from bacteria to plants to animals. Caproic acid is one of the chemicals that gives the decomposing fleshy seed coat of the ginkgo fruit its characteristic unpleasant odor. It is also one of the components of vanilla and cheese. Industrially, the primary use of caproic acid is in the manufacture of its esters for use as artificial flavors and in the manufacture of hexyl derivatives, such as hexylphenols. Caproic acid has been associated with medium chain acyl-CoA dehydrogenase deficiency, which is an inborn error of metabolism. As a relatively volatile organic compound, caproic acid has been identified as a fecal biomarker of Clostridium difficile infection (PMID: 30986230 ).
Structure
Data?1676999695
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000535 (Caproic acid)


  Mrv1652309272007422D          

  8  7  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
   -2.7297   -0.5199    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
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
M  END
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3D MOL for HMDB0000535 (Caproic acid)

HMDB0000535
     RDKit          3D
Caproic acid
 20 19  0  0  0  0  0  0  0  0999 V2000
   -2.5829   -0.2209    0.2804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6668    0.8300   -0.2964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3203    0.2271   -0.6893 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3249   -0.3586    0.5018 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6566   -0.9909    0.2768 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6878   -0.1074   -0.2375 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8324   -0.5330   -0.4669 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4245    1.2172   -0.4825 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6308    0.0538    0.0114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5109   -0.2429    1.3834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4107   -1.2225   -0.1846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4821    1.6254    0.4526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1553    1.2915   -1.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5784   -0.5686   -1.4492 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2266    0.9922   -1.2288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3857   -1.0585    0.9859 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4656    0.4722    1.2531 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0325   -1.4331    1.2338 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4780   -1.8922   -0.3819 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5950    1.9193    0.2201 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  2  0
  6  8  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  0
  2 13  1  0
  3 14  1  0
  3 15  1  0
  4 16  1  0
  4 17  1  0
  5 18  1  0
  5 19  1  0
  8 20  1  0
M  END
Download

3D SDF for HMDB0000535 (Caproic acid)


  Mrv1652309272007422D          

  8  7  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
   -2.7297   -0.5199    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
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000535

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H12O2/c1-2-3-4-5-6(7)8/h2-5H2,1H3,(H,7,8)

> <INCHI_KEY>
FUZZWVXGSFPDMH-UHFFFAOYSA-N

> <FORMULA>
C6H12O2

> <MOLECULAR_WEIGHT>
116.1583

> <EXACT_MASS>
116.083729628

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
13.269938207309668

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
hexanoic acid

> <ALOGPS_LOGP>
1.88

> <JCHEM_LOGP>
1.8108961276666666

> <ALOGPS_LOGS>
-1.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.090214000852688

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
31.0736

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.72e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hexanoic acid

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0000535 (Caproic acid)

HMDB0000535
     RDKit          3D
Caproic acid
 20 19  0  0  0  0  0  0  0  0999 V2000
   -2.5829   -0.2209    0.2804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6668    0.8300   -0.2964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3203    0.2271   -0.6893 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3249   -0.3586    0.5018 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6566   -0.9909    0.2768 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6878   -0.1074   -0.2375 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8324   -0.5330   -0.4669 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4245    1.2172   -0.4825 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6308    0.0538    0.0114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5109   -0.2429    1.3834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4107   -1.2225   -0.1846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4821    1.6254    0.4526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1553    1.2915   -1.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5784   -0.5686   -1.4492 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2266    0.9922   -1.2288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3857   -1.0585    0.9859 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4656    0.4722    1.2531 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0325   -1.4331    1.2338 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4780   -1.8922   -0.3819 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5950    1.9193    0.2201 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  2  0
  6  8  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  0
  2 13  1  0
  3 14  1  0
  3 15  1  0
  4 16  1  0
  4 17  1  0
  5 18  1  0
  5 19  1  0
  8 20  1  0
M  END
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PDB for HMDB0000535 (Caproic 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      -5.095  -0.970   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -5.095   0.567   0.000  0.00  0.00           O+0
HETATM    8  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                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END
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3D PDB for HMDB0000535 (Caproic acid)

COMPND    HMDB0000535
HETATM    1  C1  UNL     1      -2.583  -0.221   0.280  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.667   0.830  -0.296  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.320   0.227  -0.689  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.325  -0.359   0.502  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.657  -0.991   0.277  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.688  -0.107  -0.238  1.00  0.00           C  
HETATM    7  O1  UNL     1       3.832  -0.533  -0.467  1.00  0.00           O  
HETATM    8  O2  UNL     1       2.425   1.217  -0.483  1.00  0.00           O  
HETATM    9  H1  UNL     1      -3.631   0.054   0.011  1.00  0.00           H  
HETATM   10  H2  UNL     1      -2.511  -0.243   1.383  1.00  0.00           H  
HETATM   11  H3  UNL     1      -2.411  -1.223  -0.185  1.00  0.00           H  
HETATM   12  H4  UNL     1      -1.482   1.625   0.453  1.00  0.00           H  
HETATM   13  H5  UNL     1      -2.155   1.292  -1.182  1.00  0.00           H  
HETATM   14  H6  UNL     1      -0.578  -0.569  -1.449  1.00  0.00           H  
HETATM   15  H7  UNL     1       0.227   0.992  -1.229  1.00  0.00           H  
HETATM   16  H8  UNL     1      -0.386  -1.058   0.986  1.00  0.00           H  
HETATM   17  H9  UNL     1       0.466   0.472   1.253  1.00  0.00           H  
HETATM   18  H10 UNL     1       2.033  -1.433   1.234  1.00  0.00           H  
HETATM   19  H11 UNL     1       1.478  -1.892  -0.382  1.00  0.00           H  
HETATM   20  H12 UNL     1       2.595   1.919   0.220  1.00  0.00           H  
CONECT    1    2    9   10   11
CONECT    2    3   12   13
CONECT    3    4   14   15
CONECT    4    5   16   17
CONECT    5    6   18   19
CONECT    6    7    7    8
CONECT    8   20
END
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SMILES for HMDB0000535 (Caproic acid)

CCCCCC(O)=O
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INCHI for HMDB0000535 (Caproic acid)

InChI=1S/C6H12O2/c1-2-3-4-5-6(7)8/h2-5H2,1H3,(H,7,8)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
1-Hexanoic acidChEBI
1-Pentanecarboxylic acidChEBI
6:0ChEBI
Butylacetic acidChEBI
C6:0ChEBI
Capronic acidChEBI
CH3-[CH2]4-COOHChEBI
HexanoateChEBI
Hexoic acidChEBI
Hexylic acidChEBI
N-Caproic acidChEBI
N-Hexanoic acidChEBI
N-Hexoic acidChEBI
N-Hexylic acidChEBI
Pentanecarboxylic acidChEBI
Pentiformic acidChEBI
Pentylformic acidChEBI
1-HexanoateGenerator
1-PentanecarboxylateGenerator
ButylacetateGenerator
CapronateGenerator
Hexanoic acidGenerator
HexoateGenerator
HexylateGenerator
N-CaproateGenerator
N-HexanoateGenerator
N-HexoateGenerator
N-HexylateGenerator
PentanecarboxylateGenerator
PentiformateGenerator
PentylformateGenerator
CaproateGenerator
Hexanoic acid, calcium saltMeSH, HMDB
Hexanoic acid, sodium salt, 1-(11)C-labeledMeSH, HMDB
Hexanoic acid, nickel (2+) saltMeSH, HMDB
Hexanoic acid, sodium saltMeSH, HMDB
Bismuth(III)hexanoateMeSH, HMDB
Hexanoic acid, copper (2+) saltMeSH, HMDB
Hexanoic acid, manganese (2+) saltMeSH, HMDB
Bi(ohex)3MeSH, HMDB
Hexanoic acid, barium saltMeSH, HMDB
Hexanoic acid, potassium saltMeSH, HMDB
Hexanoic acid, rhodium (2+) saltMeSH, HMDB
FA(6:0)HMDB
Calcium N-hexanoateMeSH, HMDB
Hexanoic acid, sodium salt (1:1)MeSH, HMDB
Sodium capronateMeSH, HMDB
Calcium hexanoateMeSH, HMDB
Caproic acid sodium saltMeSH, HMDB
Sodium caproateMeSH, HMDB
Sodium hexanoateMeSH, HMDB
Chemical FormulaC6H12O2
Average Molecular Weight116.1583
Monoisotopic Molecular Weight116.083729628
IUPAC Namehexanoic acid
Traditional Namehexanoic acid
CAS Registry Number142-62-1
SMILES
CCCCCC(O)=O
InChI Identifier
InChI=1S/C6H12O2/c1-2-3-4-5-6(7)8/h2-5H2,1H3,(H,7,8)
InChI KeyFUZZWVXGSFPDMH-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
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point-4.00 to -3.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point202.00 to 203.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility10.3 mg/mLNot Available
LogP1.92HANSCH,C ET AL. (1995)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg128.53830932474
[M-H]-Not Available128.538http://allccs.zhulab.cn/database/detail?ID=AllCCS00000199
Predicted Molecular Properties
PropertyValueSource
Water Solubility9.72 g/LALOGPS
logP1.88ALOGPS
logP1.81ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)5.09ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity31.07 m³·mol⁻¹ChemAxon
Polarizability13.27 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]+125.92931661259
DarkChem[M+H]+125.92931661259
DarkChem[M-H]-121.0131661259
DarkChem[M-H]-121.0131661259
AllCCS[M+H]+128.76932859911
AllCCS[M-H]-129.66232859911
DeepCCS[M+H]+141.87330932474
DeepCCS[M-H]-139.08830932474
DeepCCS[M-2H]-175.68630932474
DeepCCS[M+Na]+150.35930932474
AllCCS[M+H]+128.832859911
AllCCS[M+H-H2O]+124.532859911
AllCCS[M+NH4]+132.832859911
AllCCS[M+Na]+133.932859911
AllCCS[M-H]-129.732859911
AllCCS[M+Na-2H]-132.932859911
AllCCS[M+HCOO]-136.432859911

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, 2022.3.78 minutes32390414
Predicted by Siyang on May 30, 202212.1123 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20224.93 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid37.7 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Caproic acidCCCCCC(O)=O1785.2Standard polar33892256
Caproic acidCCCCCC(O)=O956.5Standard non polar33892256
Caproic acidCCCCCC(O)=O995.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Caproic acid,1TMS,isomer #1CCCCCC(=O)O[Si](C)(C)C1066.6Semi standard non polar33892256
Caproic acid,1TBDMS,isomer #1CCCCCC(=O)O[Si](C)(C)C(C)(C)C1288.4Semi standard non polar33892256
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Sweat
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified17 (0-105) uMAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified1.5 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified1 uMChildren (1-13 years old)BothNormal 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 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
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified0-3156.612 nmol/g wet fecesChildren (1-13 years old)Not Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not AvailableNormal details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothNormal details
FecesDetected and Quantified500 (0.0-3600) nmol/g wet fecesAdult (>18 years old)BothNormal 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 QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal 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 and Quantified110-220 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified74.4 +/- 94 nmol/g wet fecesAdult (>18 years old)Female
Normal		 details
FecesDetected and Quantified643.949 +/- 607.791 nmol/g wet fecesNot SpecifiedNot Specified
Normal		 details
FecesDetected and Quantified662.888 +/- 773.427 nmol/g wet fecesNot SpecifiedNot Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
    • Zerihun T. Dame, ...
 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
    • Zerihun T. Dame, ...
 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)Not SpecifiedNormal details
SalivaDetected and Quantified6.93 +/- 4.92 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
 details
SalivaDetected and Quantified8.47 +/- 4.43 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
 details
SweatDetected but not QuantifiedNot QuantifiedAdult BothNormal details
UrineDetected and Quantified3-8 umol/mmol creatinineChildren (1 - 13 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.91 +/- 1.05 umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified0.5 (0.0-1.0) umol/mmol creatinineInfant (0-1 year old)BothNormal
    • Geigy Scientific ...
 details
UrineDetected and Quantified0.46 (0.14-0.75) umol/mmol creatinineNewborn (0-30 days old)Both
Normal
    • Analysis of 40 NI...
 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Crohn's disease 		details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Clostridium difficile infection 		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
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothUlcerative colitis details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothCrohns disease details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothImmunoglobulin A nephropathy (IgAN) progressor details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothImmunoglobulin A nephropathy (IgAN) non progressor details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative colitis		 details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothPervasive Developmental Disorder Not Otherwise Specified details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothAutism details
FecesDetected and Quantified0-106090.855 nmol/g wet fecesChildren (1-13 years old)Not Specified
Treated celiac disease		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative colitis		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Irritable bowel syndrome		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative Colitis		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Clostridium difficile infection		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBreast cancer details
UrineDetected and Quantified21-137 umol/mmol creatinineChildren (1 - 13 years old)BothMedium Chain Acyl-CoA Dehydrogenase Deficiency details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer details
Associated Disorders and Diseases
Disease References
Ulcerative colitis
  1. Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
  2. Le Gall G, Noor SO, Ridgway K, Scovell L, Jamieson C, Johnson IT, Colquhoun IJ, Kemsley EK, Narbad A: Metabolomics of fecal extracts detects altered metabolic activity of gut microbiota in ulcerative colitis and irritable bowel syndrome. J Proteome Res. 2011 Sep 2;10(9):4208-18. doi: 10.1021/pr2003598. Epub 2011 Aug 8. [PubMed:21761941 ]
  3. 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 ]
  4. 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 ]
Irritable bowel syndrome
  1. Le Gall G, Noor SO, Ridgway K, Scovell L, Jamieson C, Johnson IT, Colquhoun IJ, Kemsley EK, Narbad A: Metabolomics of fecal extracts detects altered metabolic activity of gut microbiota in ulcerative colitis and irritable bowel syndrome. J Proteome Res. 2011 Sep 2;10(9):4208-18. doi: 10.1021/pr2003598. Epub 2011 Aug 8. [PubMed:21761941 ]
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Celiac disease
  1. Di Cagno R, De Angelis M, De Pasquale I, Ndagijimana M, Vernocchi P, Ricciuti P, Gagliardi F, Laghi L, Crecchio C, Guerzoni ME, Gobbetti M, Francavilla R: Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC Microbiol. 2011 Oct 4;11:219. doi: 10.1186/1471-2180-11-219. [PubMed:21970810 ]
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 ]
Pervasive developmental disorder not otherwise specified
  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. 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 ]
  2. 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 ]
Colorectal cancer
  1. 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 ]
  2. 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 ]
Clostridium difficile infection
  1. Patel M, Fowler D, Sizer J, Walton C: Faecal volatile biomarkers of Clostridium difficile infection. PLoS One. 2019 Apr 15;14(4):e0215256. doi: 10.1371/journal.pone.0215256. eCollection 2019. [PubMed:30986230 ]
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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB013897
KNApSAcK IDC00001218
Chemspider ID8552
KEGG Compound IDC01585
BioCyc IDHEXANOATE
BiGG IDNot Available
Wikipedia LinkHexanoic_acid
METLIN ID5520
PubChem Compound8892
PDB IDNot Available
ChEBI ID30776
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000184
Good Scents IDrw1008541
References
Synthesis ReferenceGao, Fei; Wu, Zongwei. Process for preparation of hexanoic acid by oxidation of 2-octanol with nitric acid. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 7pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. [PubMed:12829005 ]
  2. Jakobs C, Sweetman L, Nyhan WL: Hydroxy acid metabolites of branched-chain amino acids in amniotic fluid. Clin Chim Acta. 1984 Jul 16;140(2):157-66. [PubMed:6467607 ]
  3. Schoots AC, Mikkers FE, Cramers CA, Ringoir S: Profiling of uremic serum by high-resolution gas chromatography-electron-impact, chemical ionization mass spectrometry. J Chromatogr. 1979 Sep 11;164(1):1-8. [PubMed:541389 ]
  4. Epps JM, Phillips JO, Mestecky J: IgA-mediated clearance and tissue deposition of dinitrophenylated human serum albumin at various DNP:HSA ratios. Mol Immunol. 1988 Aug;25(8):731-8. [PubMed:3185569 ]
  5. Varani J, Orr W, Ward PA: Cell-associated proteases affect tumour cell migration in vitro. J Cell Sci. 1979 Apr;36:241-52. [PubMed:457809 ]
  6. Nilsen SL, Castellino FJ: Expression of human plasminogen in Drosophila Schneider S2 cells. Protein Expr Purif. 1999 Jun;16(1):136-43. [PubMed:10336871 ]
  7. Varani J, Orr W, Ward PA: Comparison of cell attachment and caseinolytic activities of five tumour cell types. J Cell Sci. 1978 Dec;34:133-44. [PubMed:748334 ]
  8. Hoverstad T, Fausa O, Bjorneklett A, Bohmer T: Short-chain fatty acids in the normal human feces. Scand J Gastroenterol. 1984 May;19(3):375-81. [PubMed:6740214 ]
  9. Harkness RA: Lesch-Nyhan syndrome: reduced amino acid concentrations in CSF and brain. Adv Exp Med Biol. 1989;253A:159-63. [PubMed:2624185 ]
  10. Traul KA, Driedger A, Ingle DL, Nakhasi D: Review of the toxicologic properties of medium-chain triglycerides. Food Chem Toxicol. 2000 Jan;38(1):79-98. [PubMed:10685018 ]
  11. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  12. 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 ]
  13. 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 ]
  14. 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 ]
  15. Patel M, Fowler D, Sizer J, Walton C: Faecal volatile biomarkers of Clostridium difficile infection. PLoS One. 2019 Apr 15;14(4):e0215256. doi: 10.1371/journal.pone.0215256. eCollection 2019. [PubMed:30986230 ]
  16. 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 ]
  17. 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
Enzyme Details
4. Acyl-coenzyme A synthetase ACSM1, mitochondrial
General function:
Involved in catalytic activity
Specific function:
Has medium-chain fatty acid:CoA ligase activity with broad substrate specificity (in vitro). Acts on acids from C(4) to C(11) and on the corresponding 3-hydroxy- and 2,3- or 3,4-unsaturated acids (in vitro). Functions as GTP-dependent lipoate-activating enzyme that generates the substrate for lipoyltransferase (By similarity).
Gene Name:
ACSM1
Uniprot ID:
Q08AH1
Molecular weight:
65272.74
Enzyme Details
5. Acyl-coenzyme A synthetase ACSM6, mitochondrial
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
ACSM6
Uniprot ID:
Q6P461
Molecular weight:
53584.545
Enzyme Details
6. Acyl-coenzyme A synthetase ACSM2A, mitochondrial
General function:
Involved in catalytic activity
Specific function:
Has medium-chain fatty acid:CoA ligase activity with broad substrate specificity (in vitro). Acts on acids from C(4) to C(11) and on the corresponding 3-hydroxy- and 2,3- or 3,4-unsaturated acids (in vitro) (By similarity).
Gene Name:
ACSM2A
Uniprot ID:
Q08AH3
Molecular weight:
64223.7
Enzyme Details
7. Acyl-coenzyme A synthetase ACSM2B, mitochondrial
General function:
Involved in catalytic activity
Specific function:
Has medium-chain fatty acid:CoA ligase activity with broad substrate specificity (in vitro). Acts on acids from C(4) to C(11) and on the corresponding 3-hydroxy- and 2,3- or 3,4-unsaturated acids (in vitro).
Gene Name:
ACSM2B
Uniprot ID:
Q68CK6
Molecular weight:
64270.78
Enzyme Details
8. Acyl-coenzyme A synthetase ACSM3, mitochondrial
General function:
Involved in catalytic activity
Specific function:
Has medium-chain fatty acid:CoA ligase activity with broad substrate specificity (in vitro). Acts on acids from C(4) to C(11) and on the corresponding 3-hydroxy- and 2,3- or 3,4-unsaturated acids (in vitro) (By similarity).
Gene Name:
ACSM3
Uniprot ID:
Q53FZ2
Molecular weight:
66152.235
Enzyme Details
9. Acyl-coenzyme A synthetase ACSM5, mitochondrial
General function:
Involved in catalytic activity
Specific function:
Has medium-chain fatty acid:CoA ligase activity with broad substrate specificity (in vitro). Acts on acids from C(4) to C(11) and on the corresponding 3-hydroxy- and 2,3- or 3,4-unsaturated acids (in vitro) (By similarity).
Gene Name:
ACSM5
Uniprot ID:
Q6NUN0
Molecular weight:
64759.55
Enzyme Details
10. Acyl-coenzyme A synthetase ACSM4, mitochondrial
General function:
Involved in catalytic activity
Specific function:
Has medium-chain fatty acid:CoA ligase activity with broad substrate specificity (in vitro). Acts on acids from C(4) to C(11) and on the corresponding 3-hydroxy- and 2,3- or 3,4-unsaturated acids (in vitro) (By similarity).
Gene Name:
ACSM4
Uniprot ID:
P0C7M7
Molecular weight:
65702.225