N-acetyl-L-citrulline (PAMDB120243)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB120243
Identification
Name: N-acetyl-L-citrulline
Description:The L-enantiomer of N-acetylcitrulline.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • (2S)-2-(acetylamino)-5-[(aminocarbonyl)amino]pentanoic acid
  • (S)-2-ACETAMIDO-5-UREIDOPENTANOIC ACID
Chemical Formula: C8H14N3O4
Average Molecular Weight: 216.216
Monoisotopic Molecular Weight: 217.10626
InChI Key: WMQMIOYQXNRROC-LURJTMIESA-M
InChI:InChI=1S/C8H15N3O4/c1-5(12)11-6(7(13)14)3-2-4-10-8(9)15/h6H,2-4H2,1H3,(H,11,12)(H,13,14)(H3,9,10,15)/p-1/t6-/m0/s1
CAS number: 33965-42-3
IUPAC Name:(2S)-2-acetamido-5-(carbamoylamino)pentanoic acid
Traditional IUPAC Name: N-acetylcitrulline
SMILES:CC(=O)NC(C([O-])=O)CCCNC(=O)N
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as n-acyl-alpha amino acids. These are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Organic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct Parent N-acyl-alpha amino acids
Alternative Parents
Substituents
  • N-acyl-alpha-amino acid
  • Fatty acid
  • Acetamide
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Urea
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • 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 Solubility3.57 mg/mLALOGPS
logP-2ALOGPS
logP-1.9ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)3.87ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area121.52 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity50.77 m3·mol-1ChemAxon
Polarizability21.5 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
N-acetyl-L-citrulline + Water → Citrulline + acetate
Pathways:
    Spectra
    Spectra:
    Spectrum TypeDescriptionSplash Key
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0kxr-1940000000-7ed59850116277cffabeView in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bw9-1900000000-5d45ec9fe734ecd6af0bView in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-6900000000-adef7863bd21185ec37aView in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-3920000000-2e7f6af35d579c08e195View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0adl-4900000000-de31117b4ba7585e8899View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-a969132ff1299f346efeView in MoNA
    References
    References:
    • Engelke UF, Liebrand-van Sambeek ML, de Jong JG, Leroy JG, Morava E, Smeitink JA, Wevers RA: N-acetylated metabolites in urine: proton nuclear magnetic resonance spectroscopic study on patients with inborn errors of metabolism. Clin Chem. 2004 Jan;50(1):58-66. Epub 2003 Nov 18. [14633929 ]
    Synthesis Reference: Shi, Dashuang; Morizono, Hiroki; Yu, Xiaolin; Roth, Lauren; Caldovic, Ljubica; Allewell, Norma M.; Malamy, Michael H.; Tuchman, Mendel. Crystal Structure of N-Acetylornithine Transcarbamylase from Xanthomonas campestris: A novel enzyme in a new arginine biosynthetic pathway found in several eubacteria. Journal of Biological Chemistry (2005), 280(15), 14366-14369. (Biosynthetic preparation)
    Material Safety Data Sheet (MSDS) Not Available
    External Links:
    ResourceLink
    HMDBHMDB00856
    CHEBI49001
    PUBCHEM25245924
    LIGAND-CPDC15532