Record Information
Version1.0
Creation date2010-04-08 22:09:51 UTC
Update date2018-01-23 19:18:22 UTC
Primary IDFDB011841
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameL-Citrulline
DescriptionOccurs in the juice of watermelon (Citrullus vulgaris) A non-essential amino acid and a precursor of arginine. Citrulline supplements have been claimed to promote energy levels, stimulate the immune system and help detoxify ammonia (a cell toxin). L-citrulline is made from L-ornithine and carbamoyl phosphate in one of the central reactions in the urea cycle. It is also produced from L-arginine as a by-product of the reaction catalyzed by the enzyme NO synthase. L-citrulline, while being an amino acid, is not involved in protein synthesis and is not one of the amino acids coded for by DNA. Although citrulline cannot be incorporated in proteins during protein synthesis, several proteins are known to contain citrulline as an amino acid. These citrulline residues are generated by a family of enzymes called peptidylarginine deiminases (PADs), which convert the amino acid arginine into citrulline. Proteins that contain citrulline residues include myelin basic protein (MBP), fillagrin and several histone proteins.; Citrulline is an amino acid made from ornithine and carbamoyl phosphate in one of the central reactions in the urea cycle. It is also produced from arginine as a by-product of the reaction catalyzed by NOS family (NOS; Citrulline is made from ornithine and carbamoyl phosphate in one of the central reactions in the urea cycle. It is also produced from arginine as a by-product of the reaction catalyzed by NOS family (NOS; EC 1.14.13.39). Arginine is first oxidized into N-hydroxyl-arginine, which is then further oxidized to citrulline concomitant with release of nitric oxide.; EC 1.14.13.39). Citrulline's name is derived from citrullus, the Latin word for watermelon, from which it was first isolated.; EC 1.14.13.39). In this reaction arginine is first oxidized into N-hydroxyl-arginine, which is then further oxidized to citrulline concomitant with the release of nitric oxide.; The organic compound citrulline is an ?-amino acid. Its name is derived from citrullus, the Latin word for watermelon, from which it was first isolated in 1930. It has the idealized formula H2NC(O)NH(CH2)3CH(NH2)CO2H. It is a key intermediate in the urea cycle, the pathway by which mammals excrete ammonia.; The rind of watermelon (Citrullus lanatus) is a good natural source of citrulline. L-Citrulline is found in many foods, some of which are mung bean, cucurbita (gourd), nectarine, and acorn.
CAS Number372-75-8
Structure
Thumb
Synonyms
SynonymSource
2-amino-5-Uredovaleric acidChEBI
CitChEBI
CitrulinaChEBI
DL-2-amino-5-Ureidovaleric acidChEBI
DL-CitrullineChEBI
N(5)-(Aminocarbonyl)-DL-ornithineChEBI
N(5)-(Aminocarbonyl)ornithineChEBI
N(5)-Carbamoyl-DL-ornithineChEBI
2-amino-5-UredovalerateGenerator
DL-2-amino-5-UreidovalerateGenerator
(2S)-2-amino-5-(carbamoylamino)pentanoatebiospider
(2S)-2-amino-5-(carbamoylamino)pentanoic acidbiospider
(S)-2-amino-5-(aminocarbonyl)aminopentanoatebiospider
(S)-2-amino-5-(aminocarbonyl)aminopentanoic acidbiospider
(S)-2-Amino-5-ureidopentanoatebiospider
(S)-2-Amino-5-ureidopentanoic acidbiospider
2-Amino-5-uredovaleratebiospider
2-Amino-5-ureidovaleratebiospider
2-Amino-5-ureidovaleric acidbiospider
A-amino-d-ureidovaleratebiospider
A-amino-d-ureidovaleric acidbiospider
a-amino-delta-UreidovalerateGenerator
a-amino-delta-Ureidovaleric acidGenerator
a-amino-δ-ureidovalerateGenerator
a-amino-δ-ureidovaleric acidGenerator
Alpha-amino-delta-ureidovaleratebiospider
Alpha-amino-delta-ureidovaleric acidbiospider
Alpha-amino-gamma-ureidovaleratebiospider
Alpha-amino-gamma-ureidovaleric acidbiospider
Amino-ureidovaleratebiospider
Amino-ureidovaleric acidbiospider
CIRbiospider
CITRULLINEChEBI
Citrulline, l-biospider
Citrulline; L-formdb_source
Cytrullinebiospider
D-ureidonorvalinebiospider
Delta-ureidonorvalinebiospider
Gammaureidonorvalinebiospider
H-cit-ohbiospider
L-2-Amino-5-ureido-valeratebiospider
L-2-Amino-5-ureido-valeric acidbiospider
L-2-Amino-5-ureidovaleratebiospider
L-2-Amino-5-ureidovaleric acidbiospider
L-citrulline (DCF)biospider
L-CytrullineHMDB
L-N5-carbamoyl-Ornithinebiospider
L(+)-2-Amino-5-ureidovaleratebiospider
L(+)-2-Amino-5-ureidovaleric acidbiospider
L(+)-citrullinebiospider
N-carbamylornithinebiospider
N()-CarbamylornithineHMDB
N(5)-(aminocarbonyl)-L-ornithinebiospider
N(5)-carbamoyl-L-ornithinebiospider
N(delta)-carbamylornithinebiospider
N(δ)-carbamylornithineGenerator
N5-(aminocarbonyl)ornithinebiospider
N5-(Aminocarbonyl)-L-ornithinebiospider
N5-(aminocarbonyl)-Ornithinebiospider
N5-(Aminocarbonyl)ornithinebiospider
N5-Carbamoyl-L-ornithineHMDB
N5-carbamoylornithinebiospider
N5-carbamylornithinebiospider
ND-carbamylornithinebiospider
Ndelta-carbamy-ornithinebiospider
Ndelta-carbamylornithinebiospider
Ngamma-carbamylornithinebiospider
Ornithine, N5-(aminocarbonyl)-biospider
Ornithine, N5-carbamoyl-, L- (8CI)biospider
SitrullineHMDB
Ureidonorvalinebiospider
Ureidovaleratebiospider
Ureidovaleric acidbiospider
α-amino-δ-ureidovalerateGenerator
α-amino-δ-ureidovaleric acidGenerator
δ-ureidonorvalineGenerator
Predicted Properties
PropertyValueSource
Water Solubility2.42 g/LALOGPS
logP-3.5ALOGPS
logP-4.6ChemAxon
logS-1.9ALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
DescriptionThis compound belongs to the class of chemical entities 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).
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 41.14%; H 7.48%; N 23.99%; O 27.40%DFC
Melting PointMp 222°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logP-3.19SANGSTER (1994)
Experimental pKapKa2 9.41 (25°, 0.1M NaCl)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]25D +22 (c, 2 in 1M HCl)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-2900000000-8ad50b6bfa0414858456View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02h0-9800000000-a21c873012c5b415893dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9000000000-99072cb4f63af1d1cf6fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01x3-3900000000-116f2160c869230ce0dcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06sl-6900000000-83b0717c41387086e908View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-21c686e77e72c76881e0View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID9367
ChEMBL IDCHEMBL444814
KEGG Compound IDC00327
Pubchem Compound ID9750
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB00155
HMDB IDHMDB00904
CRC / DFC (Dictionary of Food Compounds) IDGZW12-P:GZX06-V
EAFUS IDNot Available
Dr. Duke IDCITRULLINE
BIGG ID34627
KNApSAcK IDC00001348
HET IDCIR
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDCitrulline
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
ant iasthenic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti hepatotic62868 Any compound that is able to prevent damage to the liver.DUKE
anti osteoporotic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
diuretic35498 An agent that promotes the excretion of urine through its effects on kidney function.DUKE
Enzymes
NameGene NameUniProt ID
N(G),N(G)-dimethylarginine dimethylaminohydrolase 2DDAH2O95865
Argininosuccinate synthaseASS1P00966
NOS1 mutantNOS1B3VK56
Ornithine carbamoyltransferase, mitochondrialOTCP00480
Pathways
NameSMPDB LinkKEGG Link
Arginine and Proline MetabolismSMP00020 map00330
Aspartate MetabolismSMP00067 map00250
Urea CycleSMP00059 map00330
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
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).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.