| Record Information |
|---|
| Version | 1.0 |
|---|
| Creation Date | 2016-09-30 22:38:23 UTC |
|---|
| Update Date | 2020-06-04 20:48:55 UTC |
|---|
| BMDB ID | BMDB0000904 |
|---|
| Secondary Accession Numbers | |
|---|
| Metabolite Identification |
|---|
| Common Name | Citrulline |
|---|
| Description | Citrulline, 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 | |
|---|
| Synonyms | | Value | Source |
|---|
| (S)-2-Amino-5-ureidopentanoic acid | ChEBI | | 2-Amino-5-ureidovaleric acid | ChEBI | | alpha-Amino-delta-ureidovaleric acid | ChEBI | | Cit | ChEBI | | delta-Ureidonorvaline | ChEBI | | L-2-Amino-5-ureidovaleric acid | ChEBI | | N(5)-(Aminocarbonyl)-L-ornithine | ChEBI | | N5-(Aminocarbonyl)ornithine | ChEBI | | N5-Carbamoylornithine | ChEBI | | N(delta)-Carbamylornithine | ChEBI | | (S)-2-Amino-5-ureidopentanoate | Generator | | 2-Amino-5-ureidovalerate | Generator | | a-Amino-delta-ureidovalerate | Generator | | a-Amino-delta-ureidovaleric acid | Generator | | alpha-Amino-delta-ureidovalerate | Generator | | Α-amino-δ-ureidovalerate | Generator | | Α-amino-δ-ureidovaleric acid | Generator | | Δ-ureidonorvaline | Generator | | L-2-Amino-5-ureidovalerate | Generator | | N(Δ)-carbamylornithine | Generator | | a-Amino-δ-ureidovalerate | HMDB | | a-Amino-δ-ureidovaleric acid | HMDB | | (2S)-2-Amino-5-(carbamoylamino)pentanoate | HMDB | | (2S)-2-Amino-5-(carbamoylamino)pentanoic acid | HMDB | | (S)-2-Amino-5-(aminocarbonyl)aminopentanoate | HMDB | | (S)-2-Amino-5-(aminocarbonyl)aminopentanoic acid | HMDB | | 2-Amino-5-uredovalerate | HMDB | | 2-Amino-5-uredovaleric acid | HMDB | | a-Amino-D-ureidovalerate | HMDB | | a-Amino-D-ureidovaleric acid | HMDB | | alpha-Amino-gamma-ureidovalerate | HMDB | | alpha-Amino-gamma-ureidovaleric acid | HMDB | | Amino-ureidovalerate | HMDB | | Amino-ureidovaleric acid | HMDB | | CIR | HMDB | | Cytrulline | HMDB | | D-Ureidonorvaline | HMDB | | DL-Citrulline | HMDB | | Gammaureidonorvaline | HMDB | | H-Cit-OH | HMDB | | L(+)-2-Amino-5-ureidovalerate | HMDB | | L(+)-2-Amino-5-ureidovaleric acid | HMDB | | L(+)-Citrulline | HMDB | | L-2-Amino-5-ureido-valerate | HMDB | | L-2-Amino-5-ureido-valeric acid | HMDB | | L-Citrulline | HMDB | | L-Cytrulline | HMDB | | L-N5-Carbamoyl-ornithine | HMDB | | N()-Carbamylornithine | HMDB | | N(5)-(Aminocarbonyl)-DL-ornithine | HMDB | | N-Carbamylornithine | HMDB | | N5-(Aminocarbonyl)-L-ornithine | HMDB | | N5-(Aminocarbonyl)-ornithine | HMDB | | N5-Carbamoyl-L-ornithine | HMDB | | N5-Carbamylornithine | HMDB | | ND-Carbamylornithine | HMDB | | Ndelta-carbamy-ornithine | HMDB | | Ndelta-carbamylornithine | HMDB | | Ngamma-carbamylornithine | HMDB | | Sitrulline | HMDB | | Ureidonorvaline | HMDB | | Ureidovalerate | HMDB | | Ureidovaleric acid | HMDB |
|
|---|
| Chemical Formula | C6H13N3O3 |
|---|
| Average Molecular Weight | 175.1857 |
|---|
| Monoisotopic Molecular Weight | 175.095691297 |
|---|
| IUPAC Name | (2S)-2-amino-5-(carbamoylamino)pentanoic acid |
|---|
| Traditional Name | L-citrulline |
|---|
| CAS Registry Number | 372-75-8 |
|---|
| 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 Key | RHGKLRLOHDJJDR-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. |
|---|
| Kingdom | Organic compounds |
|---|
| Super Class | Organic acids and derivatives |
|---|
| Class | Carboxylic acids and derivatives |
|---|
| Sub Class | Amino acids, peptides, and analogues |
|---|
| Direct Parent | L-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 Framework | Aliphatic acyclic compounds |
|---|
| External Descriptors | |
|---|
| Ontology |
|---|
| Status | Detected and Quantified |
|---|
| Origin | |
|---|
| Biofunction | Not Available |
|---|
| Application | Not Available |
|---|
| Cellular locations | - Cytoplasm
- Mitochondria
- Myelin sheath
|
|---|
| Physical Properties |
|---|
| State | Solid |
|---|
| Experimental Properties | | Property | Value | Reference |
|---|
| Melting Point | 235.5 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 212 mg/mL | Not Available | | LogP | -3.19 | SANGSTER (1994) |
|
|---|
| Predicted Properties | |
|---|
| Spectra |
|---|
| Spectra | |
|---|
| 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 |
|---|
| |
| Bladder | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Blood | Detected and Quantified | 59.5-68.3 uM | Not Specified | Not Specified | Normal | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Blood | Detected and Quantified | 55.1 uM | Not Specified | Both | Normal | | details | | Blood | Detected and Quantified | 120-177 uM | Not Specified | Not Specified | Normal | | details | | Blood | Detected and Quantified | 71-84 uM | Not Specified | Not Specified | Normal | | details | | Blood | Detected and Quantified | 88 +/- 15 uM | Not Specified | Not Specified | Normal | | details | | Epidermis | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Fibroblasts | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Intestine | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Kidney | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected and Quantified | 20 +/- 5 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Longissimus Thoracis Muscle | Detected and Quantified | 34 +/- 12 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 4.9 +/- 0.2 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 5.0 +/- 0.1 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 4.7 +/- 0.1 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 5.0 +/- 0.1 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 59-111 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Neuron | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Placenta | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Platelet | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Prostate Tissue | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 36.8 +/- 20.5 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 37 +/- 20 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 184 +/- 74 uM | Not Specified | Not Specified | Normal | | details | | Semimembranosus Muscle | Detected and Quantified | 31 +/- 14 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Testis | Detected and Quantified | 19 +/- 7 nmol/g of tissue | Not Specified | Not Specified | Normal | | details |
|
|---|
| Abnormal Concentrations |
|---|
| |
| Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Heat stress | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | All Mycobacterium avium subsp. paratuberculosis-infected | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | High dose Mycobacterium avium subsp. paratuberculosis-infected | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Low dose Mycobacterium avium subsp. paratuberculosis-infected | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Mycobacterium avium subsp. paratuberculosis infection | | details |
|
|---|
| External Links |
|---|
| HMDB ID | HMDB0000904 |
|---|
| DrugBank ID | DB00155 |
|---|
| Phenol Explorer Compound ID | Not Available |
|---|
| FooDB ID | FDB011841 |
|---|
| KNApSAcK ID | C00001348 |
|---|
| Chemspider ID | 9367 |
|---|
| KEGG Compound ID | C00327 |
|---|
| BioCyc ID | L-CITRULLINE |
|---|
| BiGG ID | 34627 |
|---|
| Wikipedia Link | Citrulline |
|---|
| METLIN ID | 16 |
|---|
| PubChem Compound | 9750 |
|---|
| PDB ID | Not Available |
|---|
| ChEBI ID | 16349 |
|---|
| References |
|---|
| Synthesis Reference | Kakimoto, 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 | - 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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.
|
|---|