Record Information |
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Version | 1.0 |
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Creation Date | 2016-09-30 22:38:23 UTC |
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Update Date | 2020-06-04 20:48:55 UTC |
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BMDB ID | BMDB0000904 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Citrulline |
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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. |
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Structure | |
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Synonyms | Value | Source |
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(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 |
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Chemical Formula | C6H13N3O3 |
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Average Molecular Weight | 175.1857 |
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Monoisotopic Molecular Weight | 175.095691297 |
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IUPAC Name | (2S)-2-amino-5-(carbamoylamino)pentanoic acid |
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Traditional Name | L-citrulline |
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CAS Registry Number | 372-75-8 |
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SMILES | N[C@@H](CCCNC(N)=O)C(O)=O |
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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 |
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InChI Key | RHGKLRLOHDJJDR-BYPYZUCNSA-N |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | L-alpha-amino acids |
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Alternative Parents | |
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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
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Status | Detected and Quantified |
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Origin | |
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Biofunction | Not Available |
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Application | Not Available |
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Cellular locations | - Cytoplasm
- Mitochondria
- Myelin sheath
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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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) |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-0a4i-0920000000-2d92b63cd5d9648023b8 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (3 TMS) | splash10-00di-9610000000-2e7cd23afc2adcef35a3 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0a4i-0920000000-2d92b63cd5d9648023b8 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-00di-9610000000-2e7cd23afc2adcef35a3 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-007o-9100000000-1f8dd2c6648b104639c7 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-00dl-9410000000-37909012a777213f8566 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-008a-0904000000-23fbe48f82e515087d68 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-03di-5900000000-78afcbaf8b8b3eabf174 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-001i-0900000000-8fb191d4c20fd54b9282 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-00di-0900000000-da484f0362a8dca5127e | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-00e9-0900000000-46229b4f77feabb3f857 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-001i-0900000000-4aca1022c393602a297d | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-001i-0900000000-3bc2eff2e907b7734cc8 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-001i-3900000000-2613bf40e3be814da86f | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-0006-9300000000-e83287bbc060eb9cf6f3 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-001i-0900000000-daf5b8d935c6f60c6df7 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-00e9-0900000000-46229b4f77feabb3f857 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-001i-0900000000-4aca1022c393602a297d | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-001i-0900000000-322d7f0082e7d5c6ebee | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-001i-3900000000-2613bf40e3be814da86f | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0006-9300000000-e83287bbc060eb9cf6f3 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-03di-5900000000-78afcbaf8b8b3eabf174 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-001i-0900000000-8fb191d4c20fd54b9282 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-00di-0900000000-da484f0362a8dca5127e | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-001i-0900000000-daf5b8d935c6f60c6df7 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-001i-0900000000-20fe8593ca8d8303d73a | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-001i-0900000000-a2851fcef80bb0d9b984 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0a4i-0900000000-4c1d7af748a47e489949 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-00di-9000000000-988fced362fc0da157c9 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-00di-9000000000-0818e0e8bcee12692498 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-004j-0900000000-5fa8a338dcd2f2a6bdd2 | View in MoNA |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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2D NMR | [1H,1H] 2D NMR Spectrum | Not Available | View in JSpectraViewer |
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2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | View in JSpectraViewer |
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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 |
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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.
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