Hexanoic acid (BioCAD00000012096)

blood cerebrospinal fluid (csf) feces saliva sweat urine placenta

Metabolite Card

Formula: C6H12O2 (116.0837)
SMILES: CCCCCC(O)=O

Synonyms [en]

hexanoic acid; caproic acid; Pentylformic acid; Butylacetic acid; hexanoate; C6:0

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Hexanoic acid. 数据之源，洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000012096). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

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).

Cytoplasm Extracellular Membrane
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 142-62-1
  • CAS Registry Number: 56279-38-0
  • CAS Registry Number: 58454-02-7
  • CAS Registry Number: 68603-84-9
  • CAS Registry Number: 70248-25-8
  • PubChem: 8892
  • ChEBI: ChEBI:17120
  • ChEBI: ChEBI:30776
  • HMDB: HMDB0000535
  • HMDB: HMDB00535
  • LipidMaps: LMFA01010006
  • KEGG: C01585
  • BioCyc: HEXANOATE
  • NCBI MeSH: hexanoic acid
  • Wikipedia: Caproic_acid
  • Wikipedia: Hexanoic_acid
  • RefMet: RM0137067
  • MoNA: FiehnHILIC000411
  • MoNA: FiehnHILIC001983
  • MoNA: FiehnLibVolatile0211
  • MoNA: HMDB0000535_c_ms_909
  • MoNA: HMDB0000535_ms_ms_755
  • MoNA: HMDB0000535_ms_ms_756
  • MoNA: HMDB0000535_ms_ms_757
  • MoNA: JP009185
  • MoNA: KO000426
  • MoNA: KO000427
  • MoNA: KO000428
  • MoNA: KO000429
  • MoNA: MT000145
  • MoNA: PS024901
  • Metlin: METLIN_111
  • Coconut NaturalProduct: CNP0210437.0

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R03620 3.5.1.39 N-methylhexanamide amidohydrolase
Rhea:RHEA:20082 3.5.1.39 N-methylhexanamide + H2O => hexanoate + methylamine
Rhea:RHEA:20083 3.5.1.39 hexanoate + methylamine => N-methylhexanamide + H2O
Rhea:RHEA:20084 3.5.1.39 N-methylhexanamide + H2O <=> hexanoate + methylamine
Rhea:RHEA:38888 N-hexanoyl-sphinganine + H2O => hexanoate + sphinganine
Rhea:RHEA:38889 hexanoate + sphinganine => N-hexanoyl-sphinganine + H2O
Rhea:RHEA:38890 N-hexanoyl-sphinganine + H2O <=> hexanoate + sphinganine
Rhea:RHEA:40116 hexanoyl-CoA + H2O => hexanoate + CoA + H+
Rhea:RHEA:40117 hexanoate + CoA + H+ => hexanoyl-CoA + H2O
Rhea:RHEA:40118 hexanoyl-CoA + H2O <=> hexanoate + CoA + H+
Rhea:RHEA:40612 trihexanoylglycerol + H2O => 2,3-dihexanoyl-sn-glycerol + hexanoate + H+
Rhea:RHEA:40613 2,3-dihexanoyl-sn-glycerol + hexanoate + H+ => trihexanoylglycerol + H2O
Rhea:RHEA:40614 trihexanoylglycerol + H2O <=> 2,3-dihexanoyl-sn-glycerol + hexanoate + H+
Rhea:RHEA:41296 N-(hexanoyl)sphing-4-enine + H2O => hexanoate + sphing-4-enine
Rhea:RHEA:41297 hexanoate + sphing-4-enine => N-(hexanoyl)sphing-4-enine + H2O
Rhea:RHEA:41298 N-(hexanoyl)sphing-4-enine + H2O <=> hexanoate + sphing-4-enine
Rhea:RHEA:43741 hexanoate + ATP + CoA => hexanoyl-CoA + AMP + diphosphate
Rhea:RHEA:43742 hexanoyl-CoA + AMP + diphosphate => hexanoate + ATP + CoA
Rhea:RHEA:43743 hexanoate + ATP + CoA <=> hexanoyl-CoA + AMP + diphosphate
Rhea:RHEA:47353 a hexanoate ester + H2O => an aliphatic alcohol + hexanoate + H+
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Organism Source

Taxonomy Source

  1. Actaea dahurica [ncbi taxid: 64029]
  2. Actaea heracleifolia [ncbi taxid: 64034]
  3. Actaea simplex [ncbi taxid: 64042]
  4. Ailanthus altissima [ncbi taxid: ]
  5. Akebia quinata [ncbi taxid: 13331]
  6. Akebia trifoliata [ncbi taxid: 155132]
  7. Artemisia capillaries [ncbi taxid: ]
  8. Attalea speciosa [ncbi taxid: 145700]
  9. Brassica hirta [ncbi taxid: ]
  10. Bupleurum chinense [ncbi taxid: 52451]
  11. Bupleurum falcatum [ncbi taxid: 46367]
  12. Bupleurum scorzonerifolium [ncbi taxid: 48105]
  13. Capsicum annuum [ncbi taxid: 4072]
  14. Cimicifuga foetida [ncbi taxid: ]
  15. Cinamomum cassia [ncbi taxid: ]
  16. Cinnamomum aromaticum [ncbi taxid: 119260]
  17. Clostridium autoethanogenum + Clostridium kluyveri [ncbi taxid: ]
  18. Clostridium kluyveri. + Methanogen 166 [ncbi taxid: ]
  19. Cocos nucifera [ncbi taxid: 13894]
  20. Crocus sativus [ncbi taxid: 82528]
  21. Cucumis melo [ncbi taxid: 3656]
  22. Cucurbita maxima [ncbi taxid: 3661]
  23. Cucurbita pepo [ncbi taxid: 3663]
  24. Dioscorea species [ncbi taxid: ]
  25. Drymaria cordata [ncbi taxid: 191453]
  26. Elsholtzia ciliata [ncbi taxid: 662901]
  27. Eucalyptus globulus [ncbi taxid: 34317]
  28. Ficus carica [ncbi taxid: 3494]
  29. FOOD SAKE [ncbi taxid: ]
  30. Fragaria x ananassa [ncbi taxid: 3747]
  31. Ganoderma lucidum [ncbi taxid: 5315]
  32. Gardenia jasminoides [ncbi taxid: 114476]
  33. Glehnia littoralis [ncbi taxid: 48119]
  34. Hansenia forbesii [ncbi taxid: 165499]
  35. Hansenia weberbaueriana [ncbi taxid: 54724]
  36. Hippophae rhamnoides [ncbi taxid: 193516]
  37. Homo sapiens [ncbi taxid: 9606]
  38. Kobus ellipsiprymnus [ncbi taxid: 9962]
  39. Mosla chinensis [ncbi taxid: 516065]
  40. Ostericum grosseserratum [ncbi taxid: 182415]
  41. Panax ginseng [ncbi taxid: 4054]
  42. Panax notoginseng [ncbi taxid: 44586]
  43. Panax quinquefolium [ncbi taxid: ]
  44. Panax quinquefolius [ncbi taxid: 44588]
  45. Panicum miliaceum [ncbi taxid: 4540]
  46. Papaver somniferum [ncbi taxid: 3469]
  47. Phyllosma capensis [ncbi taxid: 430983]
  48. Piper nigrum [ncbi taxid: 13216]
  49. Proustia ilicifolia [ncbi taxid: ]
  50. Schisandra chinensis [ncbi taxid: 50507]
  51. Senna alexandrina [ncbi taxid: 72402]
  52. Solanum tuberosum [ncbi taxid: 4113]
  53. Spongiporus leucomallellus (Murril) [ncbi taxid: ]
  54. Sraitia grosvenorii [ncbi taxid: ]
  55. Streptomyces sp. A0916 [ncbi taxid: ]
  56. Syzygium aromaticum [ncbi taxid: 219868]
  57. Theobroma cacao [ncbi taxid: 3641]
  58. Vaccinium corymbosum [ncbi taxid: 69266]
  59. Vaccinium myrtillus [ncbi taxid: 180763]
  60. Vitis vinifera [ncbi taxid: 29760]
  61. Zanthoxylum nitidum [ncbi taxid: 354528]
  62. Zea mays [ncbi taxid: 4577]
  63. Zingiber officinale [ncbi taxid: 94328]
  64. Ziziphus jujuba [ncbi taxid: 326968]

Pathway Synthetic

pathway id name
PathBank:SMP0001035 fatty acid oxidation (hexanoate)
PathBank:SMP0121348 Fatty Acid Oxidation (Hexanoate)
PathBank:SMP0000568 Short-Chain 3-Hydroxyacyl-CoA Dehydrogenase Deficiency (SCHAD)
PathBank:SMP0087350 Fatty Acid Biosynthesis
PathBank:SMP0087358 Mitochondrial Beta-Oxidation of Short Chain Saturated Fatty Acids
PathBank:SMP0120632 Short-Chain 3-Hydroxyacyl-CoA Dehydrogenase Deficiency (SCHAD)
PathBank:SMP0087257 Fatty Acid Biosynthesis
PathBank:SMP0087265 Mitochondrial Beta-Oxidation of Short Chain Saturated Fatty Acids
PathBank:SMP0087409 Fatty Acid Biosynthesis
PathBank:SMP0063641 Mitochondrial Beta-Oxidation of Short Chain Saturated Fatty Acids
PathBank:SMP0087416 Mitochondrial Beta-Oxidation of Short Chain Saturated Fatty Acids
PathBank:SMP0120851 Short-Chain 3-Hydroxyacyl-CoA Dehydrogenase Deficiency (SCHAD)
PathBank:SMP0000456 Fatty Acid Biosynthesis
PathBank:SMP0000480 Mitochondrial Beta-Oxidation of Short Chain Saturated Fatty Acids
PathBank:SMP0002360 Fatty Acid Biosynthesis
PathBank:SMP0087499 Fatty Acid Biosynthesis
PathBank:SMP0087519 Mitochondrial Beta-Oxidation of Short Chain Saturated Fatty Acids
PathBank:SMP0063613 Fatty Acid Biosynthesis
View All Pathways