Showing metabocard for 2-Oxoarginine (BMDB0004225)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 23:08:36 UTC
Update Date2020-05-21 16:28:31 UTC
BMDB IDBMDB0004225
Secondary Accession Numbers
  • BMDB04225
Metabolite Identification
Common Name2-Oxoarginine
Description2-Oxoarginine 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. 2-Oxoarginine is possibly soluble (in water) and a very strong basic compound (based on its pKa). 2-Oxoarginine can be biosynthesized from D-arginine through the action of the enzyme D-amino-acid oxidase. In cattle, 2-oxoarginine is involved in the metabolic pathway called the D-arginine and D-ornithine metabolism pathway. 2-Oxoarginine is a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-oxo-5-Guanidino-pentanoateChEBI
2-oxo-5-GuanidinopentanoateChEBI
2-oxo-5-Guanidinovaleric acidChEBI
5-((Aminoiminomethyl)amino)-2-oxopentanoic acidChEBI
5-Guanidino-2-oxo-pentanoateChEBI
5-Guanidino-2-oxopentanoateChEBI
alpha-Keto-delta-guanidinopentanoic acidChEBI
alpha-Keto-delta-guanidinovaleric acidChEBI
2-oxo-5-Guanidino-pentanoic acidGenerator
2-oxo-5-Guanidinopentanoic acidGenerator
2-oxo-5-GuanidinovalerateGenerator
5-((Aminoiminomethyl)amino)-2-oxopentanoateGenerator
5-Guanidino-2-oxo-pentanoic acidGenerator
5-Guanidino-2-oxopentanoic acidGenerator
a-Keto-delta-guanidinopentanoateGenerator
a-Keto-delta-guanidinopentanoic acidGenerator
alpha-Keto-delta-guanidinopentanoateGenerator
Α-keto-δ-guanidinopentanoateGenerator
Α-keto-δ-guanidinopentanoic acidGenerator
a-Keto-delta-guanidinovalerateGenerator
a-Keto-delta-guanidinovaleric acidGenerator
alpha-Keto-delta-guanidinovalerateGenerator
Α-keto-δ-guanidinovalerateGenerator
Α-keto-δ-guanidinovaleric acidGenerator
a-Keto-δ-guanidinovalerateHMDB
a-Keto-δ-guanidinovaleric acidHMDB
a-Keto-δ-guanidinopentanoateHMDB
a-Keto-δ-guanidinopentanoic acidHMDB
5-(Diaminomethylideneamino)-2-oxopentanoateHMDB
5-(Diaminomethylideneamino)-2-oxopentanoic acidHMDB
5-Guanidino-2-oxovaleric acidHMDB
a-Keto-D-guanidinovaleric acidHMDB
D-Guanidino-a-oxovaleric acidHMDB
D-Guanido-a-ketovaleric acidHMDB
delta-Guanidino-alpha-oxovaleric acidHMDB
delta-Guanido-alpha-ketovaleric acidHMDB
2-OxoarginineChEBI
5-[(Aminoiminomethyl)amino]-2-oxopentanoic acidPhytoBank
δ-Guanidino-α-oxovaleric acidPhytoBank
δ-Guanido-α-ketovaleric acidPhytoBank
Chemical FormulaC6H11N3O3
Average Molecular Weight173.1698
Monoisotopic Molecular Weight173.080041233
IUPAC Name5-[(diaminomethylidene)amino]-2-oxopentanoic acid
Traditional Name5-[(diaminomethylidene)amino]-2-oxopentanoic acid
CAS Registry Number3715-10-4
SMILES
NC(N)=NCCCC(=O)C(O)=O
InChI Identifier
InChI=1S/C6H11N3O3/c7-6(8)9-3-1-2-4(10)5(11)12/h1-3H2,(H,11,12)(H4,7,8,9)
InChI KeyARBHXJXXVVHMET-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
  • Alpha-hydroxy ketone
  • Guanidine
  • Ketone
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Membrane
  • Peroxisome
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.4ALOGPS
logP-2.4ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)3.01ChemAxon
pKa (Strongest Basic)10.71ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area118.77 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity41.23 m³·mol⁻¹ChemAxon
Polarizability16.72 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0096-9100000000-303513b0b209bca56206View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00r6-9710000000-95bf9765fd1fa4c2cd82View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-0900000000-4c337e4db09d448ecc63View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0563-9600000000-d97800b4db5ae44aebbaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-9200000000-6286bbf95e4a4716e7d4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-2900000000-67d1c875d2da6e075630View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9800000000-1a3c6500b4d652bcaadbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-89a2ffbc759f6a2a5922View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-2900000000-48efdecf4dbd7823ddffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08fu-6900000000-0ca535d235f66409d225View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000x-9000000000-82063658464a6dc17369View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-1900000000-05cd70e6e18e08b35be8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0900-7900000000-aec8a82d0097632e2cc6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9000000000-c27deb914dc894c12d6cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-2900000000-fcee1bc9a64cc54c8a61View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014m-9100000000-884cb4184447c0cb50bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ox-9000000000-d71574817dabeaf6e5e0View in MoNA
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Membrane
  • Peroxisome
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0004225
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023338
KNApSAcK IDNot Available
Chemspider ID542
KEGG Compound IDC03771
BioCyc IDCPD-824
BiGG ID42500
Wikipedia LinkNot Available
METLIN ID7030
PubChem Compound558
PDB IDNot Available
ChEBI ID28116
References
Synthesis ReferenceChibata, Ichiro; Kakimoto, Toshio; Nabe, Koichi; Shibatani, Takeji. a-Keto-d-guanidinovalerianic acid. Jpn. Kokai Tokkyo Koho (1975), 4 pp.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. D-aspartate oxidase
General function:
Amino acid transport and metabolism
Specific function:
Not Available
Gene Name:
DDO
Uniprot ID:
P31228
Molecular weight:
37660.0
Reactions
D-Arginine + Water + Oxygen → 2-Oxoarginine + Ammonia + Hydrogen peroxidedetails