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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-05-30 20:55:51 UTC

HMDB ID

HMDB0000535

Secondary Accession Numbers

HMDB00535
HMDB0061883
HMDB61883

Metabolite Identification

Common Name

Caproic acid

Description

Caproic 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

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1-Hexanoic acid	ChEBI
1-Pentanecarboxylic acid	ChEBI
6:0	ChEBI
Butylacetic acid	ChEBI
C6:0	ChEBI
Capronic acid	ChEBI
CH3-[CH2]4-COOH	ChEBI
Hexanoate	ChEBI
Hexoic acid	ChEBI
Hexylic acid	ChEBI
N-Caproic acid	ChEBI
N-Hexanoic acid	ChEBI
N-Hexoic acid	ChEBI
N-Hexylic acid	ChEBI
Pentanecarboxylic acid	ChEBI
Pentiformic acid	ChEBI
Pentylformic acid	ChEBI
1-Hexanoate	Generator
1-Pentanecarboxylate	Generator
Butylacetate	Generator
Capronate	Generator
Hexanoic acid	Generator
Hexoate	Generator
Hexylate	Generator
N-Caproate	Generator
N-Hexanoate	Generator
N-Hexoate	Generator
N-Hexylate	Generator
Pentanecarboxylate	Generator
Pentiformate	Generator
Pentylformate	Generator
Caproate	Generator
Hexanoic acid, calcium salt	MeSH, HMDB
Hexanoic acid, sodium salt, 1-(11)C-labeled	MeSH, HMDB
Hexanoic acid, nickel (2+) salt	MeSH, HMDB
Hexanoic acid, sodium salt	MeSH, HMDB
Bismuth(III)hexanoate	MeSH, HMDB
Hexanoic acid, copper (2+) salt	MeSH, HMDB
Hexanoic acid, manganese (2+) salt	MeSH, HMDB
Bi(ohex)3	MeSH, HMDB
Hexanoic acid, barium salt	MeSH, HMDB
Hexanoic acid, potassium salt	MeSH, HMDB
Hexanoic acid, rhodium (2+) salt	MeSH, HMDB
FA(6:0)	HMDB
Calcium N-hexanoate	MeSH, HMDB
Hexanoic acid, sodium salt (1:1)	MeSH, HMDB
Sodium capronate	MeSH, HMDB
Calcium hexanoate	MeSH, HMDB
Caproic acid sodium salt	MeSH, HMDB
Sodium caproate	MeSH, HMDB
Sodium hexanoate	MeSH, HMDB

Chemical Formula

C₆H₁₂O₂

Average Molecular Weight

116.1583

Monoisotopic Molecular Weight

116.083729628

IUPAC Name

hexanoic acid

Traditional Name

hexanoic acid

CAS Registry Number

142-62-1

SMILES

CCCCCC(O)=O

InChI Identifier

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

InChI Key

FUZZWVXGSFPDMH-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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Medium-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 Framework

Aliphatic acyclic compounds

External Descriptors

medium-chain fatty acid (CHEBI:30776 )
straight-chain saturated fatty acid (CHEBI:30776 )
Straight chain fatty acids (C01585 )
Saturated fatty acids (C01585 )
Straight chain fatty acids (LMFA01010006 )

Ontology

Not Available

Feces (PMID: 27275383)

Source

Endogenous

Endogenous (HMDB: HMDB0061883)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-4.00 to -3.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	202.00 to 203.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	10.3 mg/mL	Not Available
LogP	1.92	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	128.538	30932474
[M-H]-	Not Available	128.538	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000199

Predicted Molecular Properties

Property	Value	Source
Water Solubility	9.72 g/L	ALOGPS
logP	1.88	ALOGPS
logP	1.81	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	5.09	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	31.07 m³·mol⁻¹	ChemAxon
Polarizability	13.27 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	125.929	31661259
DarkChem	[M+H]+	125.929	31661259
DarkChem	[M-H]-	121.01	31661259
DarkChem	[M-H]-	121.01	31661259
AllCCS	[M+H]+	128.769	32859911
AllCCS	[M-H]-	129.662	32859911
DeepCCS	[M+H]+	141.873	30932474
DeepCCS	[M-H]-	139.088	30932474
DeepCCS	[M-2H]-	175.686	30932474
DeepCCS	[M+Na]+	150.359	30932474
AllCCS	[M+H]+	128.8	32859911
AllCCS	[M+H-H2O]+	124.5	32859911
AllCCS	[M+NH4]+	132.8	32859911
AllCCS	[M+Na]+	133.9	32859911
AllCCS	[M-H]-	129.7	32859911
AllCCS	[M+Na-2H]-	132.9	32859911
AllCCS	[M+HCOO]-	136.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Caproic acid	CCCCCC(O)=O	1785.2	Standard polar	33892256
Caproic acid	CCCCCC(O)=O	956.5	Standard non polar	33892256
Caproic acid	CCCCCC(O)=O	995.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Caproic acid,1TMS,isomer #1	CCCCCC(=O)O[Si](C)(C)C	1066.6	Semi standard non polar	33892256
Caproic acid,1TBDMS,isomer #1	CCCCCC(=O)O[Si](C)(C)C(C)(C)C	1288.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Caproic acid GC-MS (1 TMS)	splash10-00yi-3900000000-8d7942410dfae70c7c9d	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Caproic acid EI-B (Non-derivatized)	splash10-03di-9000000000-f4bf00b677d90d54ba69	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Caproic acid GC-MS (Non-derivatized)	splash10-00yi-3900000000-8d7942410dfae70c7c9d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Caproic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-9ee618fa3c0bd9d56748	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Caproic acid GC-MS (1 TMS) - 70eV, Positive	splash10-00fr-9200000000-be939d8c0455d1af93a6	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Caproic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Caproic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Caproic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-03di-9000000000-fe3fab44832ddab1082e	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Caproic acid Quattro_QQQ 10V, Negative-QTOF (Annotated)	splash10-014i-0900000000-ba8c7078846c268d61a6	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Caproic acid Quattro_QQQ 25V, Negative-QTOF (Annotated)	splash10-03di-0900000000-151d5971be58b6799d2e	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Caproic acid Quattro_QQQ 40V, Negative-QTOF (Annotated)	splash10-02t9-1900000000-36096ef7dfebaa193910	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Caproic acid EI-B (HITACHI M-80B) , Positive-QTOF	splash10-03di-9000000000-f4bf00b677d90d54ba69	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Caproic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOF	splash10-014i-0900000000-f5b00c5e9d90d801ab16	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Caproic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOF	splash10-014i-0900000000-5013166dd3b692762812	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Caproic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOF	splash10-014i-5900000000-52b3e7f8b01498621772	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Caproic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOF	splash10-0006-9000000000-e3af905666760ff49069	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Caproic acid LC-ESI-QQ , negative-QTOF	splash10-014i-0900000000-f5b00c5e9d90d801ab16	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Caproic acid LC-ESI-QQ , negative-QTOF	splash10-014i-0900000000-5013166dd3b692762812	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Caproic acid LC-ESI-QQ , negative-QTOF	splash10-014i-5900000000-52b3e7f8b01498621772	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Caproic acid LC-ESI-QQ , negative-QTOF	splash10-0006-9000000000-e3af905666760ff49069	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Caproic acid LC-ESI-IT , negative-QTOF	splash10-01b9-6900000000-763e9a8e0f15e13fae3c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Caproic acid 35V, Positive-QTOF	splash10-0002-9000000000-df670aaa002d77689cc7	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caproic acid 10V, Positive-QTOF	splash10-014j-9700000000-5489131065e0934751a7	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caproic acid 20V, Positive-QTOF	splash10-05fs-9100000000-68f7c2883fb339578ace	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caproic acid 40V, Positive-QTOF	splash10-0a4l-9000000000-8e5e925d60baa2f176c2	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caproic acid 10V, Negative-QTOF	splash10-014i-2900000000-e877f22e42e8323f59e3	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caproic acid 20V, Negative-QTOF	splash10-01b9-9800000000-b5d583466919719819a1	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caproic acid 40V, Negative-QTOF	splash10-0a4l-9000000000-791ecce51d7cdde8f0f5	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caproic acid 10V, Positive-QTOF	splash10-05tg-9000000000-b176d73a7b4fabde1ad4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caproic acid 20V, Positive-QTOF	splash10-006x-9000000000-08e066ae069da04a8689	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caproic acid 40V, Positive-QTOF	splash10-052f-9000000000-808b7302aa744c7a1c20	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caproic acid 10V, Negative-QTOF	splash10-0002-9000000000-21c5ae8d52f2e0f4cd33	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caproic acid 20V, Negative-QTOF	splash10-004j-9000000000-3e67c250e6a67f63a0dd	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Saliva
Sweat
Urine

Tissue Locations

Placenta

Pathways

Name	SMPDB/PathBank	KEGG
Biosynthesis of unsaturated fatty acids	Not Available
Fatty Acid Biosynthesis		Not Available
Mitochondrial Beta-Oxidation of Short Chain Saturated Fatty Acids		Not Available
Short-chain 3-hydroxyacyl-CoA dehydrogenase deficiency (SCHAD)		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	17 (0-105) uM	Adult (>18 years old)	Both	Normal	8412012	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	1 uM	Children (1-13 years old)	Both	Normal	8412012	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	1.5 uM	Adult (>18 years old)	Not Specified	Normal	8412012	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	19167006	details
Feces	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Both	Normal	24130822	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Specified	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Specified	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	26806034	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	19573517	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	23454028	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24811995	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24029555	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	21761941	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected and Quantified	500 (0.0-3600) nmol/g wet feces	Adult (>18 years old)	Both	Normal	6740214	details
Feces	Detected and Quantified	662.888 +/- 773.427 nmol/g wet feces	Not Specified	Not Specified	Normal	19573517	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Available	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	18085514	details
Feces	Detected and Quantified	643.949 +/- 607.791 nmol/g wet feces	Not Specified	Not Specified	Normal	20669995	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	21494609	details
Feces	Detected and Quantified	74.4 +/- 94 nmol/g wet feces	Adult (>18 years old)	Female	Normal	23997757	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	17314143	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	20669995	details
Feces	Detected and Quantified	110-220 nmol/g wet feces	Adult (>18 years old)	Both	Normal	25479871	details
Feces	Detected and Quantified	0-3156.612 nmol/g wet feces	Children (1-13 years old)	Not Specified	Normal	21970810	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24922509	details
Saliva	Detected and Quantified	6.93 +/- 4.92 uM	Adult (>18 years old)	Not Specified	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	8.47 +/- 4.43 uM	Adult (>18 years old)	Not Specified	Normal	Sugimoto et al. (...	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	12097436	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Sweat	Detected but not Quantified	Not Quantified	Adult	Both	Normal	26755145	details
Urine	Detected and Quantified	0.91 +/- 1.05 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	2026685	details
Urine	Detected and Quantified	3-8 umol/mmol creatinine	Children (1 - 13 years old)	Both	Normal	6616873	details
Urine	Detected and Quantified	0.46 (0.14-0.75) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	Analysis of 40 NI...	details
Urine	Detected and Quantified	0.5 (0.0-1.0) umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	Geigy Scientific ...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	22284503	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Both	Autism	24130822	details
Feces	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Both	Pervasive Developmental Disorder Not Otherwise Specified	24130822	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Crohns disease	26806034	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ulcerative colitis	26806034	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Nonalcoholic fatty liver disease (NAFLD)	23454028	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ulcerative colitis	24811995	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Crohn's disease	24811995	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Irritable bowel syndrome	21761941	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ulcerative colitis	21761941	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Clostridium difficile infection	30986230	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Campylobacter jejuni infection	17314143	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Clostridium difficile infection	17314143	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ulcerative Colitis	17314143	details
Feces	Detected and Quantified	0-106090.855 nmol/g wet feces	Children (1-13 years old)	Not Specified	Treated celiac disease	21970810	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Immunoglobulin A nephropathy (IgAN) non progressor	24922509	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Immunoglobulin A nephropathy (IgAN) progressor	24922509	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Breast cancer	22284503	details
Urine	Detected and Quantified	21-137 umol/mmol creatinine	Children (1 - 13 years old)	Both	Medium Chain Acyl-CoA Dehydrogenase Deficiency	6616873	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	28157703	details

Associated Disorders and Diseases

Disease References

Ulcerative colitis
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 ] 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 ] 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 ] 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
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
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
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
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
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
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 ] 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
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 ] 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
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
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
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

212750 (Celiac disease)
209850 (Autism)
266600 (Crohn's disease)
114500 (Colorectal cancer)
201450 (Medium Chain Acyl-CoA Dehydrogenase Deficiency)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Hexanoic_acid

METLIN ID

5520

PubChem Compound

8892

PDB ID

Not Available

ChEBI ID

30776

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00000184

Good Scents ID

rw1008541

References

Synthesis Reference

Gao, 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)

Not Available

General References

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 ]
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 ]
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 ]
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 ]
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 ]
Nilsen SL, Castellino FJ: Expression of human plasminogen in Drosophila Schneider S2 cells. Protein Expr Purif. 1999 Jun;16(1):136-43. [PubMed:10336871 ]
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 ]
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 ]
Harkness RA: Lesch-Nyhan syndrome: reduced amino acid concentrations in CSF and brain. Adv Exp Med Biol. 1989;253A:159-63. [PubMed:2624185 ]
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 ]
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 ]
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 ]
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 ]
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

Showing metabocard for Caproic acid (HMDB0000535)

MOL for HMDB0000535 (Caproic acid)

3D MOL for HMDB0000535 (Caproic acid)

3D SDF for HMDB0000535 (Caproic acid)

3D-SDF for HMDB0000535 (Caproic acid)

PDB for HMDB0000535 (Caproic acid)

3D PDB for HMDB0000535 (Caproic acid)

SMILES for HMDB0000535 (Caproic acid)

INCHI for HMDB0000535 (Caproic acid)

Structure for HMDB0000535 (Caproic acid)

3D Structure for HMDB0000535 (Caproic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes