Showing metabocard for N-a-Acetylcitrulline (BMDB0000856)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:37:36 UTC
Update Date2020-04-21 18:20:43 UTC
BMDB IDBMDB0000856
Secondary Accession Numbers
  • BMDB00856
Metabolite Identification
Common NameN-a-Acetylcitrulline
DescriptionN-a-Acetylcitrulline belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. N-a-Acetylcitrulline is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-(Acetylamino)-5-[(aminocarbonyl)amino]pentanoic acidChEBI
2-(Acetylamino)-5-[(aminocarbonyl)amino]pentanoateGenerator
(2S)-2-(acetylamino)-5-[(Aminocarbonyl)amino]pentanoateHMDB
(2S)-2-(acetylamino)-5-[(Aminocarbonyl)amino]pentanoic acidHMDB
(2S)-2-acetamido-5-(carbamoylamino)PentanoateHMDB
(2S)-2-acetamido-5-(carbamoylamino)Pentanoic acidHMDB
(S)-2-acetamido-5-UreidopentanoateHMDB
(S)-2-acetamido-5-Ureidopentanoic acidHMDB
a-N-AcetylcitrullineHMDB
alpha-N-AcetylcitrullineHMDB
N-Acetyl citrullineHMDB
N-Acetyl-L-citrullineHMDB
N-alpha-AcetylcitrullineHMDB
N2-Acetyl-N5-carbamoyl-L-ornithineHMDB
Na-acetyl-L-citrullineHMDB
OLNHMDB
N-a-AcetylcitrullineGenerator
N-Α-acetylcitrullineGenerator
Chemical FormulaC8H15N3O4
Average Molecular Weight217.2224
Monoisotopic Molecular Weight217.106255983
IUPAC Name5-(carbamoylamino)-2-acetamidopentanoic acid
Traditional NameN-acetylcitrulline
CAS Registry Number33965-42-3
SMILES
CC(=O)NC(CCCNC(N)=O)C(O)=O
InChI Identifier
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)
InChI KeyWMQMIOYQXNRROC-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-acyl-alpha amino acids
Alternative Parents
Substituents
  • N-acyl-alpha-amino acid
  • Fatty acid
  • Acetamide
  • Carboxamide group
  • Carbonic acid derivative
  • Secondary carboxylic acid amide
  • Urea
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
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-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 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity50.77 m³·mol⁻¹ChemAxon
Polarizability21.5 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, Positivesplash10-006x-9200000000-f6d5688503af7aafea4dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-006x-9320000000-fd58d2411a6c566e354fView in MoNA
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
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022282
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11506771
PDB IDNot Available
ChEBI ID49006
References
Synthesis ReferenceShi, 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
General ReferencesNot Available