5-Aminopentanoic acid (CHEM021787)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:12:29 UTC
Update Date2016-11-09 01:17:22 UTC
Accession NumberCHEM021787
Identification
Common Name5-Aminopentanoic acid
ClassSmall Molecule
DescriptionA delta-amino acid comprising pentanoic acid with an amino substituent at C-5; a methylene homologue of gamma-aminobutyric acid (GABA) that is a weak GABA agonist.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
5-Amino-N-valeric acidChEBI
5-AminopentanoateChEBI
5-Aminovaleric acidChEBI
DANVAChEBI
delta-Amino-N-valeric acidChEBI
delta-Aminovaleric acidChEBI
5-Amino-N-valerateGenerator
5-AminovalerateGenerator
delta-Amino-N-valerateGenerator
Δ-amino-N-valerateGenerator
Δ-amino-N-valeric acidGenerator
delta-AminovalerateGenerator
Δ-aminovalerateGenerator
Δ-aminovaleric acidGenerator
5-Aminovaleric acid hydrochlorideMeSH
5-Aminopentanoic acidKEGG
5-Amino-pentanoateGenerator, HMDB
Chemical FormulaC5H11NO2
Average Molecular Mass117.146 g/mol
Monoisotopic Mass117.079 g/mol
CAS Registry Number660-88-8
IUPAC Name5-aminopentanoic acid
Traditional Name5-aminovaleric acid
SMILESNCCCCC(O)=O
InChI IdentifierInChI=1S/C5H11NO2/c6-4-2-1-3-5(7)8/h1-4,6H2,(H,7,8)
InChI KeyJJMDCOVWQOJGCB-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as delta amino acids and derivatives. Delta amino acids and derivatives are compounds containing a carboxylic acid group and an amino group at the C5 carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentDelta amino acids and derivatives
Alternative Parents
Substituents
  • Delta amino acid or derivatives
  • Straight chain fatty acid
  • Fatty acid
  • Fatty acyl
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility206 g/LALOGPS
logP-2.8ALOGPS
logP-2.4ChemAxon
logS0.24ALOGPS
pKa (Strongest Acidic)4.65ChemAxon
pKa (Strongest Basic)10.21ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity30.06 m³·mol⁻¹ChemAxon
Polarizability12.65 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00di-1900000000-37b43ab4ca79d55eaf25Spectrum
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-00fr-3910000000-9345963250dd5bb94624Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0536-9000000000-5adf6445ea3955b657bdSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-0910000000-74bd5c8746b39b3c0420Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-1900000000-37b43ab4ca79d55eaf25Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00fr-3910000000-9345963250dd5bb94624Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-1900000000-f11968cc499179c1c6dcSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00dr-4900000000-3ea14dbac57e0143438fSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fe0-4920000000-3f3f703bde631395004aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9000000000-4e782590c46224696321Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fk9-9700000000-88ec0b1d4be9919f59a4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-1900000000-2defcb7a4884b3297cacSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0f89-9500000000-5fd8b1ba2492405b08efSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0gb9-3900000000-0afcdbe5370c811ffcaaSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-0900000000-7ac1f98cc9b9752a76d6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-014i-0900000000-f5c899766b4d912df5ceSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-014i-0900000000-5e5ee374be357b4e26a4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0gb9-0900000000-969dd1eb59619aa0cf7aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0zfr-9700000000-fe04f26630dfb11c0ca0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0a4i-9000000000-fe2ccbb2c7e8d2912ff5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0a4i-9000000000-58e7344ed5410bdb1ae7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0a4i-9000000000-3f1c0f186d2397481f21Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0udi-1900000000-17b2a3b2a8a744b197fcSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-014i-0900000000-dfd5e0188b9d032c50c5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-7ac1f98cc9b9752a76d6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-f5c899766b4d912df5ceSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-5e5ee374be357b4e26a4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0900000000-dfd5e0188b9d032c50c5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0gb9-0900000000-969dd1eb59619aa0cf7aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0zfr-9700000000-fe04f26630dfb11c0ca0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-2900000000-36fcf52a7600d383116cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zgi-9600000000-e0d24cc72e765633ef93Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-177c4dd0230c5c481274Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-4900000000-50c9e3e40bbc639d1f2eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ba-9500000000-f55ea028ca0fae6c620bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-83bf020782f77c2d4ef7Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0003355
FooDB IDFDB023151
Phenol Explorer IDNot Available
KNApSAcK IDC00052162
BiGG IDNot Available
BioCyc ID5-AMINOPENTANOATE
METLIN ID6902
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID135
ChEBI ID15887
PubChem Compound ID138
Kegg Compound IDC00431
YMDB IDNot Available
ECMDB IDM2MDB005341
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10930630
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11991139
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=1268741
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=1316620
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=15150230
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=2823166
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=3004997
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=4031870
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=4301045
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=494814
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=6031429
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=6408913
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=6436440
14. Allan, Robin D.; Dickenson, Helena W.; Johnston, Graham A. R.; Kazlauskas, Rymantas; Tran, Hue W. Synthesis of analogs of GABA. XIV. Synthesis and activity of unsaturated derivatives of 5-aminopentanoic acid (d-aminovaleric acid). Australian Journal of Chemistry (1985), 38(11), 1651-6.
15. Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.
16. Sun HZ, Shi K, Wu XH, Xue MY, Wei ZH, Liu JX, Liu HY: Lactation-related metabolic mechanism investigated based on mammary gland metabolomics and 4 biofluids' metabolomics relationships in dairy cows. BMC Genomics. 2017 Dec 2;18(1):936. doi: 10.1186/s12864-017-4314-1.
17. Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.
18. Allan, Robin D.; Dickenson, Helena W.; Johnston, Graham A. R.; Kazlauskas, Rymantas; Tran, Hue W. Synthesis of analogs of GABA. XIV. Synthesis and activity of unsaturated derivatives of 5-aminopentanoic acid (d-aminovaleric acid). Australian Journal of Chemistry (1985), 38(11), 1651-6.
19. Santos A, Zanetta S, Cresteil T, Deroussent A, Pein F, Raymond E, Vernillet L, Risse ML, Boige V, Gouyette A, Vassal G: Metabolism of irinotecan (CPT-11) by CYP3A4 and CYP3A5 in humans. Clin Cancer Res. 2000 May;6(5):2012-20.
20. Sparreboom A, de Jonge MJ, de Bruijn P, Brouwer E, Nooter K, Loos WJ, van Alphen RJ, Mathijssen RH, Stoter G, Verweij J: Irinotecan (CPT-11) metabolism and disposition in cancer patients. Clin Cancer Res. 1998 Nov;4(11):2747-54.
21. Fujita K, Ando Y, Narabayashi M, Miya T, Nagashima F, Yamamoto W, Kodama K, Araki K, Endo H, Sasaki Y: Gefitinib (Iressa) inhibits the CYP3A4-mediated formation of 7-ethyl-10-(4-amino-1-piperidino)carbonyloxycamptothecin but activates that of 7-ethyl-10-[4-N-(5-aminopentanoic acid)-1-piperidino]carbonyloxycamptothecin from irinotecan. Drug Metab Dispos. 2005 Dec;33(12):1785-90. Epub 2005 Aug 25.
22. Poujol S, Pinguet F, Malosse F, Astre C, Ychou M, Culine S, Bressolle F: Sensitive HPLC-fluorescence method for irinotecan and four major metabolites in human plasma and saliva: application to pharmacokinetic studies. Clin Chem. 2003 Nov;49(11):1900-8.
23. van den Berg GA, Nagel GT, Muskiet FA, Halie MR: Mass fragmentographic identification of polyamine metabolites in the urine of normal persons and cancer patients, and its relevance to the use of polyamines as tumour markers. J Chromatogr. 1985 May 3;339(2):223-31.
24. Syrjanen S, Piironen P, Markkanen H: Free amino-acid content of wax-stimulated human whole saliva as related to periodontal disease. Arch Oral Biol. 1987;32(9):607-10.
25. Fothergill JC, Guest JR: Catabolism of L-lysine by Pseudomonas aeruginosa. J Gen Microbiol. 1977 Mar;99(1):139-55.
26. Callery PS, Geelhaar LA: Biosynthesis of 5-aminopentanoic acid and 2-piperidone from cadaverine and 1-piperideine in mouse. J Neurochem. 1984 Dec;43(6):1631-4.
27. Callery PS, Geelhaar LA: 1-Piperideine as an in vivo precursor of the gamma-aminobutyric acid homologue 5-aminopentanoic acid. J Neurochem. 1985 Sep;45(3):946-8.
28. Cole KR, Castellino FJ: The binding of antifibrinolytic amino acids to kringle-4-containing fragments of plasminogen. Arch Biochem Biophys. 1984 Mar;229(2):568-75.
29. Shin JH, Park SH, Oh YH, Choi JW, Lee MH, Cho JS, Jeong KJ, Joo JC, Yu J, Park SJ, Lee SY: Metabolic engineering of Corynebacterium glutamicum for enhanced production of 5-aminovaleric acid. Microb Cell Fact. 2016 Oct 7;15(1):174. doi: 10.1186/s12934-016-0566-8.