Record Information
Version1.0
Creation date2011-09-21 00:28:19 UTC
Update date2015-10-09 22:33:02 UTC
Primary IDFDB023338
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2-Oxoarginine
Description2-Oxoarginine is a guanidino compound metabolite of arginine catabolism. 2-Oxoarginine levels are increased in patients with argininemia (OMIM:207800). Argininemia, characterized by arginase deficiency (EC 3.5.3.1, catalyzes the last step of the urea cycle) is an autosomal recessive inborn error of metabolism caused by a defect in the final step in the urea cycle, the hydrolysis of arginine to urea and ornithine. Accumulation of arginine metabolites (such as guanidino compounds) especially 2-oxoarginine, may produce the central nervous system damage in argininemia. (PMID: 3433275, 1588833, 1690873, 819629) [HMDB]
CAS Number3715-10-4
Structure
Thumb
Synonyms
SynonymSource
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
2-Oxo-5-guanidinovaleric acidhmdb
5-(diaminomethylideneamino)-2-oxopentanoatehmdb
5-(diaminomethylideneamino)-2-oxopentanoic acidhmdb
a-keto-d-Guanidinovaleric acidhmdb
a-keto-delta-GuanidinopentanoateGenerator
a-keto-delta-Guanidinopentanoic acidGenerator
a-keto-delta-GuanidinovalerateGenerator
a-keto-delta-Guanidinovaleric acidGenerator
a-keto-δ-guanidinopentanoateGenerator
a-keto-δ-guanidinopentanoic acidGenerator
a-keto-δ-guanidinovalerateGenerator
a-keto-δ-guanidinovaleric acidGenerator
alpha-keto-delta-GuanidinopentanoateGenerator
alpha-keto-delta-Guanidinopentanoic acidChEBI
alpha-keto-delta-GuanidinovalerateGenerator
alpha-keto-delta-Guanidinovaleric acidhmdb
d-Guanidino-a-oxovaleric acidhmdb
d-Guanido-a-ketovaleric acidhmdb
α-keto-δ-guanidinopentanoateGenerator
α-keto-δ-guanidinopentanoic acidGenerator
α-keto-δ-guanidinovalerateGenerator
α-keto-δ-guanidinovaleric acidGenerator
Predicted Properties
PropertyValueSource
Water Solubility1.97 g/LALOGPS
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC6H11N3O3
IUPAC name5-[(diaminomethylidene)amino]-2-oxopentanoic acid
InChI IdentifierInChI=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
Isomeric SMILESNC(N)=NCCCC(=O)C(O)=O
Average Molecular Weight173.1698
Monoisotopic Molecular Weight173.080041233
Classification
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS2-Oxoarginine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0096-9100000000-303513b0b209bca56206Spectrum
Predicted GC-MS2-Oxoarginine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00r6-9710000000-95bf9765fd1fa4c2cd82Spectrum
Predicted GC-MS2-Oxoarginine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-0900000000-4c337e4db09d448ecc63Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0563-9600000000-d97800b4db5ae44aebbaSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-9200000000-6286bbf95e4a4716e7d4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-2900000000-67d1c875d2da6e075630Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9800000000-1a3c6500b4d652bcaadbSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-89a2ffbc759f6a2a5922Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-2900000000-48efdecf4dbd7823ddffSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08fu-6900000000-0ca535d235f66409d225Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000x-9000000000-82063658464a6dc17369Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-1900000000-05cd70e6e18e08b35be8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0900-7900000000-aec8a82d0097632e2cc6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9000000000-c27deb914dc894c12d6cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-2900000000-fcee1bc9a64cc54c8a61Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014m-9100000000-884cb4184447c0cb50bdSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ox-9000000000-d71574817dabeaf6e5e0Spectrum
NMRNot Available
ChemSpider ID542
ChEMBL IDNot Available
KEGG Compound IDC03771
Pubchem Compound ID558
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB04225
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID42500
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
Pathways
NameSMPDB LinkKEGG Link
D-Arginine and D-Ornithine MetabolismSMP00036 map00472
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference