5-guanidino-2-oxo-pentanoate (PAMDB110003)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB110003
Identification
Name: 5-guanidino-2-oxo-pentanoate
Description:Zwitterionic form of 5-guanidino-2-oxopentanoic acid.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 2-oxo-5-guanidinopentanoate
  • 2-oxo-5-guanidino-pentanoate
  • 5-carbamimidamido-2-oxopentanoate
  • α-ketoarginine
  • 2-oxoarginine
  • 5-guanidino-2-oxopentanoate
  • 2-keto-5-guanidinovalerate
  • 2-ketoarginine
Chemical Formula: C6H11N3O3
Average Molecular Weight: 173.17
Monoisotopic Molecular Weight: 174.0878662671
InChI Key: ARBHXJXXVVHMET-UHFFFAOYSA-N
InChI: InChI=1S/C6H11N3O3/c7-6(8)9-3-1-2-4(10)5(11)12/h1-3H2,(H,11,12)(H4,7,8,9)
CAS number: 3715-10-4
IUPAC Name:5-{[amino(iminio)methyl]amino}-2-oxopentanoate
Traditional IUPAC Name: 5-[(diaminomethylidene)amino]-2-oxopentanoic acid
SMILES:C(C(CCCNC(N)=[N+])=O)(=O)[O-]
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Organic acids and derivatives
Sub ClassKeto acids and derivatives
Direct Parent Short-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 Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:0
Melting point: Not Available
Experimental Properties:
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility4.06 mg/mLALOGPS
logP-1.3ALOGPS
logP-2.4ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)3.01ChemAxon
pKa (Strongest Basic)10.71ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area118.77 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity41.23 m3·mol-1ChemAxon
Polarizability16.72 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
Pathways:
  • D-Arginine and D-Ornithine Metabolism pae00472
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
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, 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, 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
References
References:
  • Mizutani N, Hayakawa C, Ohya Y, Watanabe K, Watanabe Y, Mori A: Guanidino compounds in hyperargininemia. Tohoku J Exp Med. 1987 Nov;153(3):197-205. [3433275 ]
  • Marescau B, Qureshi IA, De Deyn P, Letarte J, Ryba R, Lowenthal A: Guanidino compounds in plasma, urine and cerebrospinal fluid of hyperargininemic patients during therapy. Clin Chim Acta. 1985 Feb 28;146(1):21-7. [3987036 ]
  • Marescau B, De Deyn PP, Lowenthal A, Qureshi IA, Antonozzi I, Bachmann C, Cederbaum SD, Cerone R, Chamoles N, Colombo JP, et al.: Guanidino compound analysis as a complementary diagnostic parameter for hyperargininemia: follow-up of guanidino compound levels during therapy. Pediatr Res. 1990 Mar;27(3):297-303. [1690873 ]
  • Marescau B, Deshmukh DR, Kockx M, Possemiers I, Qureshi IA, Wiechert P, De Deyn PP: Guanidino compounds in serum, urine, liver, kidney, and brain of man and some ureotelic animals. Metabolism. 1992 May;41(5):526-32. [1588833 ]
  • Wiechert P, Mortelmans J, Lavinha F, Clara R, Terheggen HG, Lowenthal A: Excretion of guanidino-derivates in urine of hyperargininemic patients. J Genet Hum. 1976 Mar;24(1):61-72. [819629 ]
Synthesis Reference: Chibata, 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
External Links:
ResourceLink
ChEBI58489
HMDBHMDB04225
KEGGC03771
MetaboLightsMTBLC58489
PubChem25244978