Record Information
Version1.0
Creation date2010-04-08 22:06:20 UTC
Update date2019-11-26 03:00:09 UTC
Primary IDFDB004657
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCitrullin
DescriptionCitrullin, also known as cit or 2-amino-5-uredovaleric acid, is a member of the class of compounds known as alpha amino acids. Alpha amino acids are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Citrullin is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Citrullin can be found in a number of food items such as cow milk, sesame, orange bell pepper, and pepper (c. frutescens), which makes citrullin a potential biomarker for the consumption of these food products.
CAS Number627-77-0
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility21.8 g/LALOGPS
logP-3.3ALOGPS
logP-4.6ChemAxon
logS-0.9ALOGPS
pKa (Strongest Acidic)0.012ChemAxon
pKa (Strongest Basic)15ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area119.43 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity52.27 m³·mol⁻¹ChemAxon
Polarizability17.48 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC6H13N3O3
IUPAC name2-amino-5-[(C-hydroxycarbonimidoyl)amino]pentanoic acid
InChI IdentifierInChI=1S/C6H13N3O3/c7-4(5(10)11)2-1-3-9-6(8)12/h4H,1-3,7H2,(H,10,11)(H3,8,9,12)
InChI KeyRHGKLRLOHDJJDR-UHFFFAOYSA-N
Isomeric SMILESNC(CCCNC(O)=N)C(O)=O
Average Molecular Weight175.1857
Monoisotopic Molecular Weight175.095691297
Classification
Description Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Fatty acid
  • Carbonic acid derivative
  • Amino acid
  • Urea
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSCitrullin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dl-9100000000-e529c1966775698ee6e9Spectrum
Predicted GC-MSCitrullin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCitrullin, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCitrullin, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCitrullin, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCitrullin, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCitrullin, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCitrullin, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCitrullin, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCitrullin, TBDMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0c00-2900000000-846d262ea004dcebd47d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-00di-9200000000-0ab8c8048fd2a1b5b1672021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 25V, Positivesplash10-0229-8900000000-a4497446a074f32257852021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0c00-2900000000-d70247cdb16d3102b7a92021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-056r-0900000000-80c9aa9f74a41662c41e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-0a4i-0900000000-ad997bc0667b7f4bfa212021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-08fr-0900000000-fc7c70b4f13a18da7d9c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-03di-0900000000-529fb3c691ccb8f75e512021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-2900000000-8ad50b6bfa04148584562015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02h0-9800000000-a21c873012c5b415893d2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9000000000-99072cb4f63af1d1cf6f2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01x3-3900000000-116f2160c869230ce0dc2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06sl-6900000000-83b0717c41387086e9082015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-21c686e77e72c76881e02015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05xr-1900000000-1addffa6d45f8970bb872021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9300000000-43c77c654e7b19dc73552021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9000000000-37c27f0534146cfc27722021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0089-0900000000-fc6232218e6492527c732021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01q9-2900000000-8d873455742869882e962021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-c4503bf7e22592041d5a2021-10-12View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC00790
Pubchem Compound ID833
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDCITRULLIN
BIGG IDNot Available
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
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).