Metabolite Card
Formula: C5H11NO2 (117.079)
SMILES: NCCCCC(O)=O
Synonyms [en]
5-aminopentanoic acid; 5-aminopentanoate; 5-aminovaleric acid; DANVA; 5-AMINO-N-VALERIC ACID; 5-aminovalerate
Last reviewed on 2024-06-28.
Cite this Page
5-Aminopentanoate. 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: BioCAD00000004747). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Note
5-Aminopentanoic acid (or 5-aminovalerate) is a lysine degradation product. It can be produced both endogenously or through bacterial catabolism of lysine. 5-aminovalerate is formed via the following multi-step reaction: L-lysine leads to cadverine leads to L-piperideine leads 5-aminovalerate (PMID:405455). In other words it is a metabolite of cadaverine which is formed via the intermediate, 1-piperideine (PMID:6436440). Cadaverine is a foul-smelling diamine compound produced by protein hydrolysis during putrefaction of animal tissue. High levels of 5-aminovalerate in biofluids may indicate bacterial overgrowth or endogenous tissue necrosis. In most cases endogenous 5-aminovalerate is thought to be primarily a microbial metabolite produced by the gut or oral microflora, although it can be produced endogenously. 5-aminovalerate is a normal metabolite present in human saliva, with a tendency to elevated concentration in patients with chronic periodontitis. Bacterial contamination and decomposition of salivary proteins is primarily responsible for elevated salivary levels (PMID 3481959). Beyond being a general waste product, 5-aminovalerate is also believed to act as a methylene homologue of gamma-aminobutyric acid (GABA) and functions as a weak GABA agonist (PMID:4031870). It is also known as an antifibrinolytic amino acid analog and so it functions as a weak inhibitor of the blood clotting pathway (PMID:6703712). 5- aminovalerate is an in vivo substrate of 4-aminobutyrate:2-oxoglutarate aminotransferase (PMID:4031870). It can be found in Corynebacterium (PMID:27717386).
DBLinks
- CAS Registry Number: 660-88-8
- PubChem CID: 138
- ChEBI: 15887
- HMDB: HMDB0003355
- LipidMaps: LMFA01100040
- KEGG: C00431
- BioCyc: 5-AMINOPENTANOATE
- NCBI MeSH: 5-aminovaleric acid
- Wikipedia:
Other DBLinks
- CAS Registry Number: 660-88-8
- PubChem: 138
- PubChem: 3720
- ChEBI: ChEBI:15887
- ChEBI: ChEBI:356010
- HMDB: HMDB0003355
- HMDB: HMDB03355
- LipidMaps: LMFA01100040
- KEGG: C00431
- BioCyc: 5-AMINOPENTANOATE
- NCBI MeSH: 5-aminovaleric acid
- RefMet: RM0139552
- MoNA: BAF_UVA_POS000362
- MoNA: BAF_UVA_POS000374
- MoNA: BAF_UVA_POS000375
- MoNA: BAF_UVA_POS000376
- MoNA: CCMSLIB00000578027
- MoNA: CCMSLIB00005463927
- MoNA: CCMSLIB00005463928
- MoNA: CCMSLIB00005463929
- MoNA: CCMSLIB00005720467
- MoNA: EMBL-MCF_spec128577
- MoNA: EMBL_MCF_2_0_HRMS_Library000185
- MoNA: EMBL_MCF_2_0_HRMS_Library000186
- MoNA: EMBL_MCF_2_0_HRMS_Library000270
- MoNA: FiehnHILIC000120
- MoNA: FiehnLib000638
- MoNA: FiehnLib000639
- MoNA: FiehnLib000640
- MoNA: GLS00074
- MoNA: HMDB0003355_c_ms_1307
- MoNA: HMDB0003355_ms_ms_2262
- MoNA: HMDB0003355_ms_ms_2263
- MoNA: HMDB0003355_ms_ms_2264
- MoNA: JP011893
- MoNA: KO000210
- MoNA: KO000211
- MoNA: KO000212
- MoNA: KO002308
- MoNA: KO002309
- MoNA: KO002310
- MoNA: KO002311
- MoNA: KO002312
- MoNA: MoNA002064
- MoNA: MoNA002065
- MoNA: MoNA002066
- MoNA: MoNA010609
- MoNA: MoNA010610
- MoNA: MoNA010611
- MoNA: MoNA010612
- MoNA: MoNA010613
- MoNA: MoNA010614
- MoNA: MoNA024005
- MoNA: MoNA024016
- MoNA: MoNA032221
- MoNA: MoNA032223
- MoNA: MoNA032225
- MoNA: MoNA034188
- MoNA: MoNA034189
- MoNA: MoNA034190
- MoNA: MoNA037209
- MoNA: MoNA037422
- MoNA: MoNA037927
- MoNA: OUF00072
- MoNA: PR100327
- MoNA: PR100762
- MoNA: PS075501
- MoNA: PS075502
- MoNA: PS075503
- MoNA: PS075504
- MoNA: PT107550
- MoNA: PT207550
- Metlin: METLIN_6902
- Coconut NaturalProduct: CNP0167970.0
Class / Ontology
- WishartLab ClassyFire: [Amino acids, peptides, and analogues] Amino acids, peptides, and analogues
- RefMet: [Amino FA] Amino FA
- LipidMaps: [Amino fatty acids [FA0110]] Amino fatty acids [FA0110]
- ChEBI: [CHEBI:15887] 5-aminopentanoic acid
- Coconut NaturalProduct: [Amino fatty acids] Amino fatty acids
| ID | EC Number | Name |
|---|---|---|
| KEGG:R02273 | 3.5.1.30 | 5-aminopentanamide amidohydrolase |
| KEGG:R02274 | 2.6.1.48 | 5-aminopentanoate:2-oxoglutarate aminotransferase |
| KEGG:R02276 | 3.5.1.63 | 5-acetamidopentanoate amidohydrolase |
| KEGG:R02825 | 1.4.1.12 | C00431<=>C00763 |
| KEGG:R12215 | 1.2.1.19 | 5-aminopentanal:NAD+ 1-oxidoreductase |
| BioCyc:TRANS-RXN-384 | 5-aminopentanaote:H+ symport | |
| BioCyc:VAGL-RXN | 2.6.1.48 | 5-AMINOPENTANOATE + 2-KETOGLUTARATE<=>GLT + CPD-280 |
| BioCyc:RXN0-7318 | 1.2.1.19 | CPD-12763 + NAD + WATER --> 5-AMINOPENTANOATE + NADH + 2 PROTON |
| BioCyc:RXN-8243 | 2-KETO-6-AMINO-CAPROATE + HYDROGEN-PEROXIDE --> 5-AMINOPENTANOATE + CARBON-DIOXIDE + WATER | |
| BioCyc:1.21.4.1-RXN | 1.21.4.1 | D-PROLINE + Reduced-PrdC-Proteins --> 5-AMINOPENTANOATE + Oxidized-PrdC-Proteins |
| BioCyc:AMVAL-RXN | 3.5.1.- | 5-ACETAMIDOVALERATE + WATER --> 5-AMINOPENTANOATE + ACET |
| BioCyc:5-AMINOPENTANAMIDASE-RXN | 3.5.1.30 | 5-AMINOPENTANAMIDE + WATER --> 5-AMINOPENTANOATE + AMMONIUM |