Showing Metabocard for 5-aminopentanoate (BASm0013230)
| Common Name | 5-aminopentanoate |
|---|---|
| Description | 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 ). |
| Structure | |
| Molecular Formula | C5H11NO2 |
| Average Mass | 117.14630 |
| Monoisotopic Mass | 117.07898 |
| IUPAC Name | 5-aminopentanoic acid |
| Traditional Name | 5-aminopentanoic acid |
| CAS Registry Number | 660-88-8 |
| SMILES | [NH3+]CCCCC(=O)[O-] |
| InChI Identifier | InChI=1S/C5H11NO2/c6-4-2-1-3-5(7)8/h1-4,6H2,(H,7,8) |
| InChI Key | JJMDCOVWQOJGCB-UHFFFAOYSA-N |
| CHEBI ID | CHEBI:356010 |
| HMDB ID | HMDB0003355 |
| State | Solid |
| Water Solubility | 2.06e+02 g/l |
| logP | -2.75 |
| logS | 0.24 |
| pKa (Strongest Acidic) | 4.65 |
| pKa (Strongest Basic) | 10.21 |
| Hydrogen Acceptor Count | 3 |
| Hydrogen Donor Count | 2 |
| Polar Surface Area | 63.32 Ų |
| Rotatable Bond Count | 4 |
| Physiological Charge | 0 |
| Formal Charge | 0 |
| Refractivity | 30.06 m³·mol⁻¹ |
| Polarizability | 12.65 |