Pentanoate (BioCAD00000016009)

blood breath feces saliva urine bladder epidermis neuron

Metabolite Card

Formula: C5H10O2 (102.0681)
SMILES: CCCCC(O)=O

Synonyms [en]

PENTANOIC ACID; valeric acid; n-Valeric acid; Valerianic acid; n-Pentanoate; Pentanoate

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Pentanoate. 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: BioCAD00000016009). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Valeric acid, or pentanoic acid, is a straight chain alkyl carboxylic acid with the chemical formula CH3(CH2)3COOH. Like other low molecular weight carboxylic acids, it has a very unpleasant odor. Valeric acid is commonly found in human feces, with an average concentration of 2.4 umol/g feces (range of 0.6-3.8 umol/g) (PMID:6740214). Valeric acid is produced by the gut microbiota, typically Clostridia species and other gut bacterial species such as Megasphaera massiliensis MRx0029 (PMID:30052654) via the condensation of ethanol with propionic acid (PMID:18116989). Valeric acid is largely considered as a gut microbial metabolite. Recently, valeric acid has been found to exert strong gut protective effects. Studies involving mice that received high doses of radiation showed that valeric acid replenishment (via oral gavage) elevated the survival rate of irradiated mice, protected hematogenic organs (such as the thymus and spleen), improved gastrointestinal (GI) tract function and enhanced intestinal epithelial integrity (PMID:31931652 ). Valeric acid was also found to restore the enteric bacteria taxonomic proportions and reprogram the small intestinal protein profile to normal levels. Valeric acid, like butyric acid, also appears to be a potent histone deacetylase (HDAC) inhibitor. High levels of HDAC proteins have been implicated in a variety of disease pathologies, from cancer and colitis to cardiovascular disease and neurodegeneration (PMID:30052654). Valeric acid is also found in certain plants, specifically in the perennial flowering plant valerian (Valeriana officinalis), from which it gets its name. Industrially valeric acid is primarily used is in the synthesis of its esters. Volatile esters of valeric acid tend to have pleasant odors and are used in perfumes and cosmetics. Ethyl valerate and pentyl valerate are used as food additives because of their fruity flavours. Hydrolysis of these valerate-containing food additives in the gut can also lead to the appearance of valerate in blood, urine and stool samples.

Extracellular Membrane
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 109-52-4
  • CAS Registry Number: 64118-37-2
  • CAS Registry Number: 67291-18-3
  • PubChem: 7991
  • ChEBI: ChEBI:17418
  • HMDB: HMDB0000892
  • HMDB: HMDB00892
  • LipidMaps: LMFA01010005
  • KEGG: C00803
  • NCBI MeSH: n-pentanoic acid
  • Wikipedia: Valeric acid
  • Wikipedia: Valeric_acid
  • DrugBank: DB02406
  • RefMet: RM0139464
  • MoNA: HMDB0000892_c_ms_99627
  • MoNA: HMDB0000892_c_ms_99628
  • MoNA: HMDB0000892_ms_ms_1253
  • MoNA: HMDB0000892_ms_ms_1254
  • MoNA: HMDB0000892_ms_ms_1255
  • MoNA: JP008906
  • MoNA: JP009179
  • MoNA: KO001991
  • MoNA: KO001992
  • MoNA: KO001993
  • MoNA: KO001994
  • MoNA: KO001995
  • MoNA: LipidBlast2022_953860
  • MoNA: MT000004
  • MoNA: PS031301
  • MoNA: PS031302
  • Metlin: METLIN_110
  • Coconut NaturalProduct: CNP0144818.0

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R02938 3.5.1.50 pentanamide amidohydrolase
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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. Akebia quinata [ncbi taxid: 13331]
  5. Akebia trifoliata [ncbi taxid: 155132]
  6. Apium graveolens [ncbi taxid: 4045]
  7. Araucaria cunninghamii [ncbi taxid: 56994]
  8. Arnebia euchroma [ncbi taxid: 373122]
  9. Arnebia guttata [ncbi taxid: 419289]
  10. Aspergillus violaceus [ncbi taxid: 41738]
  11. Cimicifuga foetida [ncbi taxid: ]
  12. Dipsacus asperoides [ncbi taxid: 180066]
  13. Eschweilera coriacea [ncbi taxid: 372712]
  14. Eucalyptus cladocalyx [ncbi taxid: 452569]
  15. Eucalyptus globulus [ncbi taxid: 34317]
  16. Flos lonicerae [ncbi taxid: ]
  17. FOOD SAKE [ncbi taxid: ]
  18. Hansenia forbesii [ncbi taxid: 165499]
  19. Hansenia weberbaueriana [ncbi taxid: 54724]
  20. Hericium erinaceus [ncbi taxid: 91752]
  21. Homo sapiens [ncbi taxid: 9606]
  22. Humulus lupulus [ncbi taxid: 3486]
  23. Kobus ellipsiprymnus [ncbi taxid: 9962]
  24. Lithospermum erythrorhizon [ncbi taxid: 34254]
  25. Lonicera japonica [ncbi taxid: 105884]
  26. Morus alba [ncbi taxid: 3498]
  27. Nardostachys jatamansi [ncbi taxid: 179860]
  28. Nicotiana tabacum [ncbi taxid: 4097]
  29. Ostericum grosseserratum [ncbi taxid: 182415]
  30. Peltodon longipes [ncbi taxid: ]
  31. Podocarpus elongata [ncbi taxid: ]
  32. Polygonum hydropiper [ncbi taxid: ]
  33. Porphyra tenera [ncbi taxid: ]
  34. Rehmannia glutinosa [ncbi taxid: 99300]
  35. Rhododendron mucronulatum [ncbi taxid: 105903]
  36. Salvadora persica [ncbi taxid: 4326]
  37. Ulva pertusa [ncbi taxid: 3120]
  38. Valeriana officinalis [ncbi taxid: 19953]
  39. Zingiber officinale [ncbi taxid: 94328]

Pathway Synthetic

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