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Record Information
Version1.0
Creation Date2016-09-30 22:38:23 UTC
Update Date2020-06-04 20:48:55 UTC
BMDB IDBMDB0000904
Secondary Accession Numbers
  • BMDB00904
Metabolite Identification
Common NameCitrulline
DescriptionCitrulline, also known as Cit or δ-ureidonorvaline, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. Citrulline is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalance. Citrulline exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Citrulline exists in all living species, ranging from bacteria to humans. Citrulline participates in a number of enzymatic reactions, within cattle. In particular, Citrulline can be biosynthesized from carbamoyl phosphate and ornithine through its interaction with the enzyme ornithine carbamoyltransferase, mitochondrial. In addition, Citrulline and L-aspartic acid can be converted into argininosuccinic acid; which is catalyzed by the enzyme argininosuccinate synthase. In cattle, citrulline is involved in the metabolic pathway called the urea cycle pathway. Citrulline is a potentially toxic compound.
Structure
Thumb
Synonyms
ValueSource
(S)-2-Amino-5-ureidopentanoic acidChEBI
2-Amino-5-ureidovaleric acidChEBI
alpha-Amino-delta-ureidovaleric acidChEBI
CitChEBI
delta-UreidonorvalineChEBI
L-2-Amino-5-ureidovaleric acidChEBI
N(5)-(Aminocarbonyl)-L-ornithineChEBI
N5-(Aminocarbonyl)ornithineChEBI
N5-CarbamoylornithineChEBI
N(delta)-CarbamylornithineChEBI
(S)-2-Amino-5-ureidopentanoateGenerator
2-Amino-5-ureidovalerateGenerator
a-Amino-delta-ureidovalerateGenerator
a-Amino-delta-ureidovaleric acidGenerator
alpha-Amino-delta-ureidovalerateGenerator
Α-amino-δ-ureidovalerateGenerator
Α-amino-δ-ureidovaleric acidGenerator
Δ-ureidonorvalineGenerator
L-2-Amino-5-ureidovalerateGenerator
N(Δ)-carbamylornithineGenerator
a-Amino-δ-ureidovalerateHMDB
a-Amino-δ-ureidovaleric acidHMDB
(2S)-2-Amino-5-(carbamoylamino)pentanoateHMDB
(2S)-2-Amino-5-(carbamoylamino)pentanoic acidHMDB
(S)-2-Amino-5-(aminocarbonyl)aminopentanoateHMDB
(S)-2-Amino-5-(aminocarbonyl)aminopentanoic acidHMDB
2-Amino-5-uredovalerateHMDB
2-Amino-5-uredovaleric acidHMDB
a-Amino-D-ureidovalerateHMDB
a-Amino-D-ureidovaleric acidHMDB
alpha-Amino-gamma-ureidovalerateHMDB
alpha-Amino-gamma-ureidovaleric acidHMDB
Amino-ureidovalerateHMDB
Amino-ureidovaleric acidHMDB
CIRHMDB
CytrullineHMDB
D-UreidonorvalineHMDB
DL-CitrullineHMDB
GammaureidonorvalineHMDB
H-Cit-OHHMDB
L(+)-2-Amino-5-ureidovalerateHMDB
L(+)-2-Amino-5-ureidovaleric acidHMDB
L(+)-CitrullineHMDB
L-2-Amino-5-ureido-valerateHMDB
L-2-Amino-5-ureido-valeric acidHMDB
L-CitrullineHMDB
L-CytrullineHMDB
L-N5-Carbamoyl-ornithineHMDB
N()-CarbamylornithineHMDB
N(5)-(Aminocarbonyl)-DL-ornithineHMDB
N-CarbamylornithineHMDB
N5-(Aminocarbonyl)-L-ornithineHMDB
N5-(Aminocarbonyl)-ornithineHMDB
N5-Carbamoyl-L-ornithineHMDB
N5-CarbamylornithineHMDB
ND-CarbamylornithineHMDB
Ndelta-carbamy-ornithineHMDB
Ndelta-carbamylornithineHMDB
Ngamma-carbamylornithineHMDB
SitrullineHMDB
UreidonorvalineHMDB
UreidovalerateHMDB
Ureidovaleric acidHMDB
Chemical FormulaC6H13N3O3
Average Molecular Weight175.1857
Monoisotopic Molecular Weight175.095691297
IUPAC Name(2S)-2-amino-5-(carbamoylamino)pentanoic acid
Traditional NameL-citrulline
CAS Registry Number372-75-8
SMILES
N[C@@H](CCCNC(N)=O)C(O)=O
InChI Identifier
InChI=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)/t4-/m0/s1
InChI KeyRHGKLRLOHDJJDR-BYPYZUCNSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Fatty acid
  • Isourea
  • Amino acid
  • Carboximidic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Carboximidamide
  • Amine
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Primary aliphatic amine
  • Organopnictogen compound
  • Imine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
  • Myelin sheath
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point235.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility212 mg/mLNot Available
LogP-3.19SANGSTER (1994)
Predicted Properties
PropertyValueSource
logP-3.3ALOGPS
logP-3.9ChemAxon
logS-0.9ALOGPS
pKa (Strongest Acidic)2.27ChemAxon
pKa (Strongest Basic)9.23ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area118.44 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity41.33 m³·mol⁻¹ChemAxon
Polarizability17.35 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
  • Myelin sheath
Biospecimen Locations
  • Bladder
  • Blood
  • Epidermis
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Longissimus Thoracis Muscle
  • Mammary Gland
  • Milk
  • Muscle
  • Neuron
  • Placenta
  • Platelet
  • Prostate Tissue
  • Ruminal Fluid
  • Semimembranosus Muscle
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BladderExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
BloodDetected and Quantified59.5-68.3 uMNot SpecifiedNot Specified
Normal
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
BloodDetected and Quantified55.1 uMNot SpecifiedBothNormal details
BloodDetected and Quantified120-177 uMNot SpecifiedNot Specified
Normal
details
BloodDetected and Quantified71-84 uMNot SpecifiedNot Specified
Normal
details
BloodDetected and Quantified88 +/- 15 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
IntestineExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
LiverDetected and Quantified20 +/- 5 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
Longissimus Thoracis MuscleDetected and Quantified34 +/- 12 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified4.9 +/- 0.2 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified5.0 +/- 0.1 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified4.7 +/- 0.1 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified5.0 +/- 0.1 uMNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified59-111 nmol/g of tissueNot SpecifiedNot Specified
Normal
details
NeuronExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlateletExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Prostate TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Ruminal FluidDetected and Quantified36.8 +/- 20.5 uMNot SpecifiedNot SpecifiedNormal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified37 +/- 20 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified184 +/- 74 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
Semimembranosus MuscleDetected and Quantified31 +/- 14 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
TestisDetected and Quantified19 +/- 7 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Heat stress
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
All Mycobacterium avium subsp. paratuberculosis-infected
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
High dose Mycobacterium avium subsp. paratuberculosis-infected
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Low dose Mycobacterium avium subsp. paratuberculosis-infected
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Mycobacterium avium subsp. paratuberculosis infection
details
HMDB IDHMDB0000904
DrugBank IDDB00155
Phenol Explorer Compound IDNot Available
FooDB IDFDB011841
KNApSAcK IDC00001348
Chemspider ID9367
KEGG Compound IDC00327
BioCyc IDL-CITRULLINE
BiGG ID34627
Wikipedia LinkCitrulline
METLIN ID16
PubChem Compound9750
PDB IDNot Available
ChEBI ID16349
References
Synthesis ReferenceKakimoto, Toshio; Shibatani, Takeji; Nishimura, Noriyuki; Chibata, Ichiro. Enzymic production of L-citrulline by Pseudomonas putida. Applied Microbiology (1971), 22(6), 992-9.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
  2. Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]
  3. Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735. [PubMed:29565828 ]
  4. Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]
  5. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.

Enzymes

General function:
Inorganic ion transport and metabolism
Specific function:
Produces nitric oxide (NO) which is implicated in vascular smooth muscle relaxation through a cGMP-mediated signal transduction pathway. NO mediates vascular endothelial growth factor (VEGF)-induced angiogenesis in coronary vessels and promotes blood clotting through the activation of platelets.
Gene Name:
NOS3
Uniprot ID:
P29473
Molecular weight:
133287.0
General function:
Inorganic ion transport and metabolism
Specific function:
Produces nitric oxide (NO) which is a messenger molecule with diverse functions throughout the body. In macrophages, NO mediates tumoricidal and bactericidal actions. Also has nitrosylase activity and mediates cysteine S-nitrosylation of cytoplasmic target proteins such PTGS2/COX2. As component of the iNOS-S100A8/9 transnitrosylase complex involved in the selective inflammatory stimulus-dependent S-nitrosylation of GAPDH implicated in regulation of the GAIT complex activity and probably multiple targets including ANXA5, EZR, MSN and VIM. Involved in inflammation, enhances the synthesis of proinflammatory mediators such as IL6 and IL8.
Gene Name:
NOS2
Uniprot ID:
Q27995
Molecular weight:
131208.0
General function:
Nucleotide transport and metabolism
Specific function:
One of the enzymes of the urea cycle, the metabolic pathway transforming neurotoxic amonia produced by protein catabolism into inocuous urea in the liver of ureotelic animals. Catalyzes the formation of arginosuccinate from aspartate, citrulline and ATP and together with ASL it is responsible for the biosynthesis of arginine in most body tissues.
Gene Name:
ASS1
Uniprot ID:
P14568
Molecular weight:
46417.0
Reactions
Adenosine triphosphate + Citrulline + L-Aspartic acid → Adenosine monophosphate + Pyrophosphate + Argininosuccinic aciddetails
General function:
Amino acid transport and metabolism
Specific function:
Hydrolyzes N(G),N(G)-dimethyl-L-arginine (ADMA) and N(G)-monomethyl-L-arginine (MMA) which act as inhibitors of NOS. Has therefore a role in the regulation of nitric oxide generation (By similarity).
Gene Name:
DDAH2
Uniprot ID:
Q3SX44
Molecular weight:
29780.0
General function:
Amino acid transport and metabolism
Specific function:
Hydrolyzes N(G),N(G)-dimethyl-L-arginine (ADMA) and N(G)-monomethyl-L-arginine (MMA) which act as inhibitors of NOS. Has therefore a role in the regulation of nitric oxide generation.
Gene Name:
DDAH1
Uniprot ID:
P56965
Molecular weight:
31289.0
General function:
Amino acid transport and metabolism
Specific function:
Not Available
Gene Name:
OTC
Uniprot ID:
Q9N1U7
Molecular weight:
39842.0
Reactions
Carbamoylphosphate + Ornithine → Hydrogen phosphate + Citrullinedetails