You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2007-05-22 20:51:34 UTC
Update Date2020-02-26 21:26:18 UTC
HMDB IDHMDB0006272
Secondary Accession Numbers
  • HMDB06272
Metabolite Identification
Common Name5-Amino-2-oxopentanoic acid
Description5-Amino-2-oxopentanoic acid, also known as 2-oxo-5-amino-pentanoate or alpha-keto-delta-aminopentanoate, belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms. 5-Amino-2-oxopentanoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 5-Amino-2-oxopentanoic acid exists in all living organisms, ranging from bacteria to humans. 5-amino-2-oxopentanoic acid can be biosynthesized from D-ornithine; which is mediated by the enzyme D-amino-acid oxidase. In humans, 5-amino-2-oxopentanoic acid is involved in d-arginine and d-ornithine metabolism.
Structure
Data?1582752378
Synonyms
ValueSource
2-oxo-5-Amino-pentanoateChEBI
2-oxo-5-AminopentanoateChEBI
2-oxo-5-AminovalerateChEBI
5-Amino-2-oxopentanoateChEBI
5-Amino-2-oxovaleric acidChEBI
alpha-Keto-delta-aminopentanoateChEBI
2-oxo-5-Amino-pentanoic acidGenerator
2-oxo-5-Aminopentanoic acidGenerator
2-oxo-5-Aminovaleric acidGenerator
5-Amino-2-oxovalerateGenerator
a-Keto-delta-aminopentanoateGenerator
a-Keto-delta-aminopentanoic acidGenerator
alpha-Keto-delta-aminopentanoic acidGenerator
Α-keto-δ-aminopentanoateGenerator
Α-keto-δ-aminopentanoic acidGenerator
a-Keto-δ-aminopentanoateHMDB
a-Keto-δ-aminopentanoic acidHMDB
Chemical FormulaC5H9NO3
Average Molecular Weight131.1299
Monoisotopic Molecular Weight131.058243159
IUPAC Name5-amino-2-oxopentanoic acid
Traditional Name5-amino-2-oxopentanoic acid
CAS Registry NumberNot Available
SMILES
NCCCC(=O)C(O)=O
InChI Identifier
InChI=1S/C5H9NO3/c6-3-1-2-4(7)5(8)9/h1-3,6H2,(H,8,9)
InChI KeyBWHGMFYTDQEALD-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassShort-chain keto acids and derivatives
Direct ParentShort-chain keto acids and derivatives
Alternative Parents
Substituents
  • Short-chain keto acid
  • Alpha-keto acid
  • Gamma-aminoketone
  • Alpha-hydroxy ketone
  • Amino acid or derivatives
  • Amino acid
  • Ketone
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organooxygen compound
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility56.1 g/LALOGPS
logP-2.5ALOGPS
logP-2.6ChemAxon
logS-0.37ALOGPS
pKa (Strongest Acidic)3.11ChemAxon
pKa (Strongest Basic)9.79ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area80.39 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity30.8 m³·mol⁻¹ChemAxon
Polarizability12.59 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9000000000-4f2ab9a8ceda96ab2b3d2017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fk9-9600000000-ff46e8c1649cc828f7b02017-10-06View Spectrum
MSMass Spectrum (Electron Ionization)splash10-001i-9000000000-4f2ab9a8ceda96ab2b3d2021-09-05View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02u1-4900000000-e6f994d6e834039502b02017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02td-9300000000-e8e8edb03b7aaff8ee8e2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-5b1e326206ccaec9c5d92017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-3900000000-680079416681a6d569312017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01qi-9500000000-56702f30bf4675c2b75a2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05nf-9000000000-7a44c7ada571fc80c95b2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9200000000-b31fe2b03dd6d43aaf762021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01bd-9000000000-ca1b69887ff2e7d07f6b2021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9000000000-f6e5fdeca83cd716bca72021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-223ace0a9362994292ed2021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9200000000-72f5d31ad31e1076f60b2021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9000000000-6915b5779a08500cd58e2021-09-07View Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
  • Peroxisome
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
    • Zerihun T. Dame, ...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023870
KNApSAcK IDNot Available
Chemspider ID388519
KEGG Compound IDC01110
BioCyc ID5-AMINO-2-OXOPENTANOATE
BiGG ID36830
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound439402
PDB IDNot Available
ChEBI ID49268
Food Biomarker OntologyNot Available
VMH ID5A2OPNTN
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Abolishes BNIP3-mediated apoptosis and mitochondrial damage.
Gene Name:
ACAA2
Uniprot ID:
P42765
Molecular weight:
41923.82
General function:
Involved in D-amino-acid oxidase activity
Specific function:
Regulates the level of the neuromodulator D-serine in the brain. Has high activity towards D-DOPA and contributes to dopamine synthesis. Could act as a detoxifying agent which removes D-amino acids accumulated during aging. Acts on a variety of D-amino acids with a preference for those having small hydrophobic side chains followed by those bearing polar, aromatic, and basic groups. Does not act on acidic amino acids.
Gene Name:
DAO
Uniprot ID:
P14920
Molecular weight:
39473.75
Reactions
D-Ornithine + Water + Oxygen → 5-Amino-2-oxopentanoic acid + Ammonia + Hydrogen peroxidedetails