Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2023-05-30 20:55:54 UTC |
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HMDB ID | HMDB0000904 |
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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 has the formula H2NC(O)NH(CH2)3CH(NH2)CO2H. Citrulline exists in all living species, ranging from bacteria to humans. Within humans, citrulline participates in a number of enzymatic reactions. In particular, citrulline can be biosynthesized from carbamoyl phosphate and ornithine which is catalyzed by the enzyme ornithine carbamoyltransferase. In addition, citrulline and L-aspartic acid can be converted into argininosuccinic acid through the action of the enzyme argininosuccinate synthase. In humans, citrulline is involved in the metabolic disorder called argininemia. Citrulline has also been found to be associated with several diseases such as ulcerative colitis, rheumatoid arthritis, and citrullinemia type II. Citrulline has also been linked to several inborn metabolic disorders including argininosuccinic aciduria and fumarase deficiency. Outside of the human body, citrulline is found, on average, in the highest concentration in a few different foods such as wheats, oats, and cucumbers and in a lower concentration in swiss chards, yellow wax beans, and potato. Citrulline has also been detected, but not quantified in several different foods, such as epazotes, lotus, common buckwheats, strawberry guava, and italian sweet red peppers. Citrulline is a potentially toxic compound. Proteins that normally contain citrulline residues include myelin basic protein (MBP), filaggrin, and several histone proteins, whereas other proteins, such as fibrin and vimentin are susceptible to citrullination during cell death and tissue inflammation. Citrulline is also produced as a byproduct of the enzymatic production of nitric oxide from the amino acid arginine, catalyzed by nitric oxide synthase. It is also produced from arginine as a byproduct of the reaction catalyzed by NOS family (NOS; EC1.14.13.39). |
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Structure | N[C@@H](CCCNC(N)=O)C(O)=O 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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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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Physiological effect | Not Available |
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Disposition | |
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Process | |
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Role | |
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Physical Properties |
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State | Solid |
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Experimental Molecular 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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Experimental Chromatographic Properties | Experimental Collision Cross Sections |
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Predicted Molecular Properties | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Citrulline,1TMS,isomer #1 | C[Si](C)(C)OC(=O)[C@@H](N)CCCNC(N)=O | 1921.7 | Semi standard non polar | 33892256 | Citrulline,1TMS,isomer #2 | C[Si](C)(C)N[C@@H](CCCNC(N)=O)C(=O)O | 1986.3 | Semi standard non polar | 33892256 | Citrulline,1TMS,isomer #3 | C[Si](C)(C)NC(=O)NCCC[C@H](N)C(=O)O | 2028.9 | Semi standard non polar | 33892256 | Citrulline,1TMS,isomer #4 | C[Si](C)(C)N(CCC[C@H](N)C(=O)O)C(N)=O | 1980.4 | Semi standard non polar | 33892256 | Citrulline,2TMS,isomer #1 | C[Si](C)(C)N[C@@H](CCCNC(N)=O)C(=O)O[Si](C)(C)C | 2008.7 | Semi standard non polar | 33892256 | Citrulline,2TMS,isomer #1 | C[Si](C)(C)N[C@@H](CCCNC(N)=O)C(=O)O[Si](C)(C)C | 1838.7 | Standard non polar | 33892256 | Citrulline,2TMS,isomer #1 | C[Si](C)(C)N[C@@H](CCCNC(N)=O)C(=O)O[Si](C)(C)C | 3301.8 | Standard polar | 33892256 | Citrulline,2TMS,isomer #2 | C[Si](C)(C)NC(=O)NCCC[C@H](N)C(=O)O[Si](C)(C)C | 2009.6 | Semi standard non polar | 33892256 | Citrulline,2TMS,isomer #2 | C[Si](C)(C)NC(=O)NCCC[C@H](N)C(=O)O[Si](C)(C)C | 1827.2 | Standard non polar | 33892256 | Citrulline,2TMS,isomer #2 | C[Si](C)(C)NC(=O)NCCC[C@H](N)C(=O)O[Si](C)(C)C | 3171.1 | Standard polar | 33892256 | Citrulline,2TMS,isomer #3 | C[Si](C)(C)OC(=O)[C@@H](N)CCCN(C(N)=O)[Si](C)(C)C | 1900.2 | Semi standard non polar | 33892256 | Citrulline,2TMS,isomer #3 | C[Si](C)(C)OC(=O)[C@@H](N)CCCN(C(N)=O)[Si](C)(C)C | 1910.3 | Standard non polar | 33892256 | Citrulline,2TMS,isomer #3 | C[Si](C)(C)OC(=O)[C@@H](N)CCCN(C(N)=O)[Si](C)(C)C | 3399.1 | Standard polar | 33892256 | Citrulline,2TMS,isomer #4 | C[Si](C)(C)NC(=O)NCCC[C@H](N[Si](C)(C)C)C(=O)O | 2087.1 | Semi standard non polar | 33892256 | Citrulline,2TMS,isomer #4 | C[Si](C)(C)NC(=O)NCCC[C@H](N[Si](C)(C)C)C(=O)O | 1797.8 | Standard non polar | 33892256 | Citrulline,2TMS,isomer #4 | C[Si](C)(C)NC(=O)NCCC[C@H](N[Si](C)(C)C)C(=O)O | 3129.9 | Standard polar | 33892256 | Citrulline,2TMS,isomer #5 | C[Si](C)(C)N([C@@H](CCCNC(N)=O)C(=O)O)[Si](C)(C)C | 2152.2 | Semi standard non polar | 33892256 | Citrulline,2TMS,isomer #5 | C[Si](C)(C)N([C@@H](CCCNC(N)=O)C(=O)O)[Si](C)(C)C | 1902.3 | Standard non polar | 33892256 | Citrulline,2TMS,isomer #5 | C[Si](C)(C)N([C@@H](CCCNC(N)=O)C(=O)O)[Si](C)(C)C | 3502.1 | Standard polar | 33892256 | Citrulline,2TMS,isomer #6 | C[Si](C)(C)N[C@@H](CCCN(C(N)=O)[Si](C)(C)C)C(=O)O | 2046.2 | Semi standard non polar | 33892256 | Citrulline,2TMS,isomer #6 | C[Si](C)(C)N[C@@H](CCCN(C(N)=O)[Si](C)(C)C)C(=O)O | 1919.6 | Standard non polar | 33892256 | Citrulline,2TMS,isomer #6 | C[Si](C)(C)N[C@@H](CCCN(C(N)=O)[Si](C)(C)C)C(=O)O | 3163.7 | Standard polar | 33892256 | Citrulline,2TMS,isomer #7 | C[Si](C)(C)N(C(=O)NCCC[C@H](N)C(=O)O)[Si](C)(C)C | 2093.7 | Semi standard non polar | 33892256 | Citrulline,2TMS,isomer #7 | C[Si](C)(C)N(C(=O)NCCC[C@H](N)C(=O)O)[Si](C)(C)C | 1891.3 | Standard non polar | 33892256 | Citrulline,2TMS,isomer #7 | C[Si](C)(C)N(C(=O)NCCC[C@H](N)C(=O)O)[Si](C)(C)C | 3452.1 | Standard polar | 33892256 | Citrulline,2TMS,isomer #8 | C[Si](C)(C)NC(=O)N(CCC[C@H](N)C(=O)O)[Si](C)(C)C | 2050.1 | Semi standard non polar | 33892256 | Citrulline,2TMS,isomer #8 | C[Si](C)(C)NC(=O)N(CCC[C@H](N)C(=O)O)[Si](C)(C)C | 1895.5 | Standard non polar | 33892256 | Citrulline,2TMS,isomer #8 | C[Si](C)(C)NC(=O)N(CCC[C@H](N)C(=O)O)[Si](C)(C)C | 3333.9 | Standard polar | 33892256 | Citrulline,3TMS,isomer #1 | C[Si](C)(C)NC(=O)NCCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C | 2096.3 | Semi standard non polar | 33892256 | Citrulline,3TMS,isomer #1 | C[Si](C)(C)NC(=O)NCCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1851.2 | Standard non polar | 33892256 | Citrulline,3TMS,isomer #1 | C[Si](C)(C)NC(=O)NCCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C | 2690.2 | Standard polar | 33892256 | Citrulline,3TMS,isomer #10 | C[Si](C)(C)N(CCC[C@H](N)C(=O)O)C(=O)N([Si](C)(C)C)[Si](C)(C)C | 2089.8 | Semi standard non polar | 33892256 | Citrulline,3TMS,isomer #10 | C[Si](C)(C)N(CCC[C@H](N)C(=O)O)C(=O)N([Si](C)(C)C)[Si](C)(C)C | 2058.5 | Standard non polar | 33892256 | Citrulline,3TMS,isomer #10 | C[Si](C)(C)N(CCC[C@H](N)C(=O)O)C(=O)N([Si](C)(C)C)[Si](C)(C)C | 3004.5 | Standard polar | 33892256 | Citrulline,3TMS,isomer #2 | C[Si](C)(C)OC(=O)[C@H](CCCNC(N)=O)N([Si](C)(C)C)[Si](C)(C)C | 2151.4 | Semi standard non polar | 33892256 | Citrulline,3TMS,isomer #2 | C[Si](C)(C)OC(=O)[C@H](CCCNC(N)=O)N([Si](C)(C)C)[Si](C)(C)C | 1948.9 | Standard non polar | 33892256 | Citrulline,3TMS,isomer #2 | C[Si](C)(C)OC(=O)[C@H](CCCNC(N)=O)N([Si](C)(C)C)[Si](C)(C)C | 3137.4 | Standard polar | 33892256 | Citrulline,3TMS,isomer #3 | C[Si](C)(C)N[C@@H](CCCN(C(N)=O)[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1958.1 | Semi standard non polar | 33892256 | Citrulline,3TMS,isomer #3 | C[Si](C)(C)N[C@@H](CCCN(C(N)=O)[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1929.2 | Standard non polar | 33892256 | Citrulline,3TMS,isomer #3 | C[Si](C)(C)N[C@@H](CCCN(C(N)=O)[Si](C)(C)C)C(=O)O[Si](C)(C)C | 2912.8 | Standard polar | 33892256 | Citrulline,3TMS,isomer #4 | C[Si](C)(C)OC(=O)[C@@H](N)CCCNC(=O)N([Si](C)(C)C)[Si](C)(C)C | 2019.0 | Semi standard non polar | 33892256 | Citrulline,3TMS,isomer #4 | C[Si](C)(C)OC(=O)[C@@H](N)CCCNC(=O)N([Si](C)(C)C)[Si](C)(C)C | 1976.5 | Standard non polar | 33892256 | Citrulline,3TMS,isomer #4 | C[Si](C)(C)OC(=O)[C@@H](N)CCCNC(=O)N([Si](C)(C)C)[Si](C)(C)C | 2886.8 | Standard polar | 33892256 | Citrulline,3TMS,isomer #5 | C[Si](C)(C)NC(=O)N(CCC[C@H](N)C(=O)O[Si](C)(C)C)[Si](C)(C)C | 1982.3 | Semi standard non polar | 33892256 | Citrulline,3TMS,isomer #5 | C[Si](C)(C)NC(=O)N(CCC[C@H](N)C(=O)O[Si](C)(C)C)[Si](C)(C)C | 1945.7 | Standard non polar | 33892256 | Citrulline,3TMS,isomer #5 | C[Si](C)(C)NC(=O)N(CCC[C@H](N)C(=O)O[Si](C)(C)C)[Si](C)(C)C | 2843.1 | Standard polar | 33892256 | Citrulline,3TMS,isomer #6 | C[Si](C)(C)N[C@@H](CCCNC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O | 2134.6 | Semi standard non polar | 33892256 | Citrulline,3TMS,isomer #6 | C[Si](C)(C)N[C@@H](CCCNC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O | 1953.6 | Standard non polar | 33892256 | Citrulline,3TMS,isomer #6 | C[Si](C)(C)N[C@@H](CCCNC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O | 2726.6 | Standard polar | 33892256 | Citrulline,3TMS,isomer #7 | C[Si](C)(C)NC(=O)N(CCC[C@H](N[Si](C)(C)C)C(=O)O)[Si](C)(C)C | 2084.8 | Semi standard non polar | 33892256 | Citrulline,3TMS,isomer #7 | C[Si](C)(C)NC(=O)N(CCC[C@H](N[Si](C)(C)C)C(=O)O)[Si](C)(C)C | 1950.8 | Standard non polar | 33892256 | Citrulline,3TMS,isomer #7 | C[Si](C)(C)NC(=O)N(CCC[C@H](N[Si](C)(C)C)C(=O)O)[Si](C)(C)C | 2710.0 | Standard polar | 33892256 | Citrulline,3TMS,isomer #8 | C[Si](C)(C)NC(=O)NCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C | 2247.6 | Semi standard non polar | 33892256 | Citrulline,3TMS,isomer #8 | C[Si](C)(C)NC(=O)NCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C | 1899.6 | Standard non polar | 33892256 | Citrulline,3TMS,isomer #8 | C[Si](C)(C)NC(=O)NCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C | 2812.7 | Standard polar | 33892256 | Citrulline,3TMS,isomer #9 | C[Si](C)(C)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(N)=O | 2148.0 | Semi standard non polar | 33892256 | Citrulline,3TMS,isomer #9 | C[Si](C)(C)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(N)=O | 2018.9 | Standard non polar | 33892256 | Citrulline,3TMS,isomer #9 | C[Si](C)(C)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(N)=O | 3011.0 | Standard polar | 33892256 | Citrulline,4TMS,isomer #1 | C[Si](C)(C)N[C@@H](CCCNC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C | 2076.4 | Semi standard non polar | 33892256 | Citrulline,4TMS,isomer #1 | C[Si](C)(C)N[C@@H](CCCNC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C | 2011.6 | Standard non polar | 33892256 | Citrulline,4TMS,isomer #1 | C[Si](C)(C)N[C@@H](CCCNC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C | 2401.4 | Standard polar | 33892256 | Citrulline,4TMS,isomer #2 | C[Si](C)(C)NC(=O)N(CCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C | 2047.3 | Semi standard non polar | 33892256 | Citrulline,4TMS,isomer #2 | C[Si](C)(C)NC(=O)N(CCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C | 1963.9 | Standard non polar | 33892256 | Citrulline,4TMS,isomer #2 | C[Si](C)(C)NC(=O)N(CCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C | 2366.3 | Standard polar | 33892256 | Citrulline,4TMS,isomer #3 | C[Si](C)(C)NC(=O)NCCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C | 2233.8 | Semi standard non polar | 33892256 | Citrulline,4TMS,isomer #3 | C[Si](C)(C)NC(=O)NCCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C | 1946.5 | Standard non polar | 33892256 | Citrulline,4TMS,isomer #3 | C[Si](C)(C)NC(=O)NCCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C | 2511.2 | Standard polar | 33892256 | Citrulline,4TMS,isomer #4 | C[Si](C)(C)OC(=O)[C@H](CCCN(C(N)=O)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C | 2124.9 | Semi standard non polar | 33892256 | Citrulline,4TMS,isomer #4 | C[Si](C)(C)OC(=O)[C@H](CCCN(C(N)=O)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C | 2029.8 | Standard non polar | 33892256 | Citrulline,4TMS,isomer #4 | C[Si](C)(C)OC(=O)[C@H](CCCN(C(N)=O)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C | 2843.2 | Standard polar | 33892256 | Citrulline,4TMS,isomer #5 | C[Si](C)(C)OC(=O)[C@@H](N)CCCN(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C | 2052.2 | Semi standard non polar | 33892256 | Citrulline,4TMS,isomer #5 | C[Si](C)(C)OC(=O)[C@@H](N)CCCN(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C | 2115.2 | Standard non polar | 33892256 | Citrulline,4TMS,isomer #5 | C[Si](C)(C)OC(=O)[C@@H](N)CCCN(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C | 2590.7 | Standard polar | 33892256 | Citrulline,4TMS,isomer #6 | C[Si](C)(C)N(C(=O)NCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C | 2255.5 | Semi standard non polar | 33892256 | Citrulline,4TMS,isomer #6 | C[Si](C)(C)N(C(=O)NCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C | 2064.8 | Standard non polar | 33892256 | Citrulline,4TMS,isomer #6 | C[Si](C)(C)N(C(=O)NCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C | 2519.2 | Standard polar | 33892256 | Citrulline,4TMS,isomer #7 | C[Si](C)(C)N[C@@H](CCCN(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C(=O)O | 2144.6 | Semi standard non polar | 33892256 | Citrulline,4TMS,isomer #7 | C[Si](C)(C)N[C@@H](CCCN(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C(=O)O | 2125.3 | Standard non polar | 33892256 | Citrulline,4TMS,isomer #7 | C[Si](C)(C)N[C@@H](CCCN(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C(=O)O | 2398.3 | Standard polar | 33892256 | Citrulline,4TMS,isomer #8 | C[Si](C)(C)NC(=O)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C | 2213.7 | Semi standard non polar | 33892256 | Citrulline,4TMS,isomer #8 | C[Si](C)(C)NC(=O)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C | 2050.9 | Standard non polar | 33892256 | Citrulline,4TMS,isomer #8 | C[Si](C)(C)NC(=O)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C | 2498.2 | Standard polar | 33892256 | Citrulline,5TMS,isomer #1 | C[Si](C)(C)OC(=O)[C@H](CCCNC(=O)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C | 2289.4 | Semi standard non polar | 33892256 | Citrulline,5TMS,isomer #1 | C[Si](C)(C)OC(=O)[C@H](CCCNC(=O)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C | 2100.8 | Standard non polar | 33892256 | Citrulline,5TMS,isomer #1 | C[Si](C)(C)OC(=O)[C@H](CCCNC(=O)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C | 2278.5 | Standard polar | 33892256 | Citrulline,5TMS,isomer #2 | C[Si](C)(C)N[C@@H](CCCN(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C | 2107.9 | Semi standard non polar | 33892256 | Citrulline,5TMS,isomer #2 | C[Si](C)(C)N[C@@H](CCCN(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C | 2155.1 | Standard non polar | 33892256 | Citrulline,5TMS,isomer #2 | C[Si](C)(C)N[C@@H](CCCN(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C | 2125.6 | Standard polar | 33892256 | Citrulline,5TMS,isomer #3 | C[Si](C)(C)NC(=O)N(CCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C | 2245.5 | Semi standard non polar | 33892256 | Citrulline,5TMS,isomer #3 | C[Si](C)(C)NC(=O)N(CCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C | 2071.0 | Standard non polar | 33892256 | Citrulline,5TMS,isomer #3 | C[Si](C)(C)NC(=O)N(CCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C | 2263.8 | Standard polar | 33892256 | Citrulline,5TMS,isomer #4 | C[Si](C)(C)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)N([Si](C)(C)C)[Si](C)(C)C | 2300.2 | Semi standard non polar | 33892256 | Citrulline,5TMS,isomer #4 | C[Si](C)(C)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)N([Si](C)(C)C)[Si](C)(C)C | 2247.3 | Standard non polar | 33892256 | Citrulline,5TMS,isomer #4 | C[Si](C)(C)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)N([Si](C)(C)C)[Si](C)(C)C | 2251.3 | Standard polar | 33892256 | Citrulline,6TMS,isomer #1 | C[Si](C)(C)OC(=O)[C@H](CCCN(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C | 2366.8 | Semi standard non polar | 33892256 | Citrulline,6TMS,isomer #1 | C[Si](C)(C)OC(=O)[C@H](CCCN(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C | 2254.6 | Standard non polar | 33892256 | Citrulline,6TMS,isomer #1 | C[Si](C)(C)OC(=O)[C@H](CCCN(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C | 2095.3 | Standard polar | 33892256 | Citrulline,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCCNC(N)=O | 2175.3 | Semi standard non polar | 33892256 | Citrulline,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N[C@@H](CCCNC(N)=O)C(=O)O | 2250.5 | Semi standard non polar | 33892256 | Citrulline,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)NC(=O)NCCC[C@H](N)C(=O)O | 2270.9 | Semi standard non polar | 33892256 | Citrulline,1TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)N(CCC[C@H](N)C(=O)O)C(N)=O | 2194.3 | Semi standard non polar | 33892256 | Citrulline,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N[C@@H](CCCNC(N)=O)C(=O)O[Si](C)(C)C(C)(C)C | 2471.6 | Semi standard non polar | 33892256 | Citrulline,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N[C@@H](CCCNC(N)=O)C(=O)O[Si](C)(C)C(C)(C)C | 2259.9 | Standard non polar | 33892256 | Citrulline,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N[C@@H](CCCNC(N)=O)C(=O)O[Si](C)(C)C(C)(C)C | 3231.2 | Standard polar | 33892256 | Citrulline,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)NC(=O)NCCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C | 2480.5 | Semi standard non polar | 33892256 | Citrulline,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)NC(=O)NCCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C | 2245.1 | Standard non polar | 33892256 | Citrulline,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)NC(=O)NCCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C | 3077.7 | Standard polar | 33892256 | Citrulline,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCCN(C(N)=O)[Si](C)(C)C(C)(C)C | 2393.7 | Semi standard non polar | 33892256 | Citrulline,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCCN(C(N)=O)[Si](C)(C)C(C)(C)C | 2319.5 | Standard non polar | 33892256 | Citrulline,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCCN(C(N)=O)[Si](C)(C)C(C)(C)C | 3391.2 | Standard polar | 33892256 | Citrulline,2TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)NC(=O)NCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O | 2607.7 | Semi standard non polar | 33892256 | Citrulline,2TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)NC(=O)NCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O | 2232.4 | Standard non polar | 33892256 | Citrulline,2TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)NC(=O)NCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O | 2962.9 | Standard polar | 33892256 | Citrulline,2TBDMS,isomer #5 | CC(C)(C)[Si](C)(C)N([C@@H](CCCNC(N)=O)C(=O)O)[Si](C)(C)C(C)(C)C | 2594.9 | Semi standard non polar | 33892256 | Citrulline,2TBDMS,isomer #5 | CC(C)(C)[Si](C)(C)N([C@@H](CCCNC(N)=O)C(=O)O)[Si](C)(C)C(C)(C)C | 2314.1 | Standard non polar | 33892256 | Citrulline,2TBDMS,isomer #5 | CC(C)(C)[Si](C)(C)N([C@@H](CCCNC(N)=O)C(=O)O)[Si](C)(C)C(C)(C)C | 3344.1 | Standard polar | 33892256 | Citrulline,2TBDMS,isomer #6 | CC(C)(C)[Si](C)(C)N[C@@H](CCCN(C(N)=O)[Si](C)(C)C(C)(C)C)C(=O)O | 2527.6 | Semi standard non polar | 33892256 | Citrulline,2TBDMS,isomer #6 | CC(C)(C)[Si](C)(C)N[C@@H](CCCN(C(N)=O)[Si](C)(C)C(C)(C)C)C(=O)O | 2350.6 | Standard non polar | 33892256 | Citrulline,2TBDMS,isomer #6 | CC(C)(C)[Si](C)(C)N[C@@H](CCCN(C(N)=O)[Si](C)(C)C(C)(C)C)C(=O)O | 3143.0 | Standard polar | 33892256 | Citrulline,2TBDMS,isomer #7 | CC(C)(C)[Si](C)(C)N(C(=O)NCCC[C@H](N)C(=O)O)[Si](C)(C)C(C)(C)C | 2533.6 | Semi standard non polar | 33892256 | Citrulline,2TBDMS,isomer #7 | CC(C)(C)[Si](C)(C)N(C(=O)NCCC[C@H](N)C(=O)O)[Si](C)(C)C(C)(C)C | 2329.1 | Standard non polar | 33892256 | Citrulline,2TBDMS,isomer #7 | CC(C)(C)[Si](C)(C)N(C(=O)NCCC[C@H](N)C(=O)O)[Si](C)(C)C(C)(C)C | 3243.1 | Standard polar | 33892256 | Citrulline,2TBDMS,isomer #8 | CC(C)(C)[Si](C)(C)NC(=O)N(CCC[C@H](N)C(=O)O)[Si](C)(C)C(C)(C)C | 2527.3 | Semi standard non polar | 33892256 | Citrulline,2TBDMS,isomer #8 | CC(C)(C)[Si](C)(C)NC(=O)N(CCC[C@H](N)C(=O)O)[Si](C)(C)C(C)(C)C | 2323.8 | Standard non polar | 33892256 | Citrulline,2TBDMS,isomer #8 | CC(C)(C)[Si](C)(C)NC(=O)N(CCC[C@H](N)C(=O)O)[Si](C)(C)C(C)(C)C | 3192.6 | Standard polar | 33892256 | Citrulline,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC(=O)NCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2766.7 | Semi standard non polar | 33892256 | Citrulline,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC(=O)NCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2403.7 | Standard non polar | 33892256 | Citrulline,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC(=O)NCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2765.0 | Standard polar | 33892256 | Citrulline,3TBDMS,isomer #10 | CC(C)(C)[Si](C)(C)N(CCC[C@H](N)C(=O)O)C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2747.4 | Semi standard non polar | 33892256 | Citrulline,3TBDMS,isomer #10 | CC(C)(C)[Si](C)(C)N(CCC[C@H](N)C(=O)O)C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2625.2 | Standard non polar | 33892256 | Citrulline,3TBDMS,isomer #10 | CC(C)(C)[Si](C)(C)N(CCC[C@H](N)C(=O)O)C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2982.3 | Standard polar | 33892256 | Citrulline,3TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCCNC(N)=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2793.5 | Semi standard non polar | 33892256 | Citrulline,3TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCCNC(N)=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2551.1 | Standard non polar | 33892256 | Citrulline,3TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCCNC(N)=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 3110.6 | Standard polar | 33892256 | Citrulline,3TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)N[C@@H](CCCN(C(N)=O)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2639.5 | Semi standard non polar | 33892256 | Citrulline,3TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)N[C@@H](CCCN(C(N)=O)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2511.1 | Standard non polar | 33892256 | Citrulline,3TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)N[C@@H](CCCN(C(N)=O)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 3024.8 | Standard polar | 33892256 | Citrulline,3TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCCNC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2698.5 | Semi standard non polar | 33892256 | Citrulline,3TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCCNC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2572.1 | Standard non polar | 33892256 | Citrulline,3TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCCNC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2914.6 | Standard polar | 33892256 | Citrulline,3TBDMS,isomer #5 | CC(C)(C)[Si](C)(C)NC(=O)N(CCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2667.4 | Semi standard non polar | 33892256 | Citrulline,3TBDMS,isomer #5 | CC(C)(C)[Si](C)(C)NC(=O)N(CCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2533.4 | Standard non polar | 33892256 | Citrulline,3TBDMS,isomer #5 | CC(C)(C)[Si](C)(C)NC(=O)N(CCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2927.1 | Standard polar | 33892256 | Citrulline,3TBDMS,isomer #6 | CC(C)(C)[Si](C)(C)N[C@@H](CCCNC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O | 2827.0 | Semi standard non polar | 33892256 | Citrulline,3TBDMS,isomer #6 | CC(C)(C)[Si](C)(C)N[C@@H](CCCNC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O | 2545.0 | Standard non polar | 33892256 | Citrulline,3TBDMS,isomer #6 | CC(C)(C)[Si](C)(C)N[C@@H](CCCNC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O | 2799.2 | Standard polar | 33892256 | Citrulline,3TBDMS,isomer #7 | CC(C)(C)[Si](C)(C)NC(=O)N(CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C | 2800.6 | Semi standard non polar | 33892256 | Citrulline,3TBDMS,isomer #7 | CC(C)(C)[Si](C)(C)NC(=O)N(CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C | 2523.0 | Standard non polar | 33892256 | Citrulline,3TBDMS,isomer #7 | CC(C)(C)[Si](C)(C)NC(=O)N(CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C | 2816.4 | Standard polar | 33892256 | Citrulline,3TBDMS,isomer #8 | CC(C)(C)[Si](C)(C)NC(=O)NCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2887.7 | Semi standard non polar | 33892256 | Citrulline,3TBDMS,isomer #8 | CC(C)(C)[Si](C)(C)NC(=O)NCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2475.7 | Standard non polar | 33892256 | Citrulline,3TBDMS,isomer #8 | CC(C)(C)[Si](C)(C)NC(=O)NCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2835.1 | Standard polar | 33892256 | Citrulline,3TBDMS,isomer #9 | CC(C)(C)[Si](C)(C)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(N)=O | 2825.4 | Semi standard non polar | 33892256 | Citrulline,3TBDMS,isomer #9 | CC(C)(C)[Si](C)(C)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(N)=O | 2575.2 | Standard non polar | 33892256 | Citrulline,3TBDMS,isomer #9 | CC(C)(C)[Si](C)(C)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(N)=O | 3067.1 | Standard polar | 33892256 | Citrulline,4TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N[C@@H](CCCNC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2951.6 | Semi standard non polar | 33892256 | Citrulline,4TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N[C@@H](CCCNC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2723.2 | Standard non polar | 33892256 | Citrulline,4TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N[C@@H](CCCNC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2703.8 | Standard polar | 33892256 | Citrulline,4TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)NC(=O)N(CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2914.0 | Semi standard non polar | 33892256 | Citrulline,4TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)NC(=O)N(CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2671.9 | Standard non polar | 33892256 | Citrulline,4TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)NC(=O)N(CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2729.9 | Standard polar | 33892256 | Citrulline,4TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)NC(=O)NCCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 3066.6 | Semi standard non polar | 33892256 | Citrulline,4TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)NC(=O)NCCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2659.6 | Standard non polar | 33892256 | Citrulline,4TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)NC(=O)NCCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2770.3 | Standard polar | 33892256 | Citrulline,4TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCCN(C(N)=O)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 3013.3 | Semi standard non polar | 33892256 | Citrulline,4TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCCN(C(N)=O)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2751.3 | Standard non polar | 33892256 | Citrulline,4TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCCN(C(N)=O)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 3047.8 | Standard polar | 33892256 | Citrulline,4TBDMS,isomer #5 | CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCCN(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2926.3 | Semi standard non polar | 33892256 | Citrulline,4TBDMS,isomer #5 | CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCCN(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2818.4 | Standard non polar | 33892256 | Citrulline,4TBDMS,isomer #5 | CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCCN(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2839.3 | Standard polar | 33892256 | Citrulline,4TBDMS,isomer #6 | CC(C)(C)[Si](C)(C)N(C(=O)NCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 3113.6 | Semi standard non polar | 33892256 | Citrulline,4TBDMS,isomer #6 | CC(C)(C)[Si](C)(C)N(C(=O)NCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2787.7 | Standard non polar | 33892256 | Citrulline,4TBDMS,isomer #6 | CC(C)(C)[Si](C)(C)N(C(=O)NCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2755.8 | Standard polar | 33892256 | Citrulline,4TBDMS,isomer #7 | CC(C)(C)[Si](C)(C)N[C@@H](CCCN(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O | 3022.9 | Semi standard non polar | 33892256 | Citrulline,4TBDMS,isomer #7 | CC(C)(C)[Si](C)(C)N[C@@H](CCCN(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O | 2811.1 | Standard non polar | 33892256 | Citrulline,4TBDMS,isomer #7 | CC(C)(C)[Si](C)(C)N[C@@H](CCCN(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O | 2739.9 | Standard polar | 33892256 | Citrulline,4TBDMS,isomer #8 | CC(C)(C)[Si](C)(C)NC(=O)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 3083.7 | Semi standard non polar | 33892256 | Citrulline,4TBDMS,isomer #8 | CC(C)(C)[Si](C)(C)NC(=O)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2748.3 | Standard non polar | 33892256 | Citrulline,4TBDMS,isomer #8 | CC(C)(C)[Si](C)(C)NC(=O)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2790.6 | Standard polar | 33892256 | Citrulline,5TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCCNC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 3311.2 | Semi standard non polar | 33892256 | Citrulline,5TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCCNC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2964.1 | Standard non polar | 33892256 | Citrulline,5TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCCNC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2696.3 | Standard polar | 33892256 | Citrulline,5TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N[C@@H](CCCN(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 3176.0 | Semi standard non polar | 33892256 | Citrulline,5TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N[C@@H](CCCN(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2976.1 | Standard non polar | 33892256 | Citrulline,5TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N[C@@H](CCCN(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2669.9 | Standard polar | 33892256 | Citrulline,5TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)NC(=O)N(CCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 3275.2 | Semi standard non polar | 33892256 | Citrulline,5TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)NC(=O)N(CCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2931.0 | Standard non polar | 33892256 | Citrulline,5TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)NC(=O)N(CCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2734.4 | Standard polar | 33892256 | Citrulline,5TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 3336.1 | Semi standard non polar | 33892256 | Citrulline,5TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 3045.3 | Standard non polar | 33892256 | Citrulline,5TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2704.8 | Standard polar | 33892256 | Citrulline,6TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCCN(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 3533.8 | Semi standard non polar | 33892256 | Citrulline,6TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCCN(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 3230.7 | Standard non polar | 33892256 | Citrulline,6TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCCN(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2719.3 | Standard polar | 33892256 |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - Citrulline GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-0a4i-0920000000-2d92b63cd5d9648023b8 | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Citrulline GC-MS (3 TMS) | splash10-00di-9610000000-2e7cd23afc2adcef35a3 | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Citrulline GC-EI-TOF (Non-derivatized) | splash10-0a4i-0920000000-2d92b63cd5d9648023b8 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Citrulline GC-MS (Non-derivatized) | splash10-00di-9610000000-2e7cd23afc2adcef35a3 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Citrulline GC-MS (Non-derivatized) - 70eV, Positive | splash10-007o-9100000000-1f8dd2c6648b104639c7 | 2016-09-22 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Citrulline GC-MS (1 TMS) - 70eV, Positive | splash10-00dl-9410000000-37909012a777213f8566 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Citrulline GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Citrulline GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Citrulline GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-11-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Citrulline GC-MS (TMS_1_3) - 70eV, Positive | Not Available | 2021-11-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Citrulline GC-MS (TMS_1_4) - 70eV, Positive | Not Available | 2021-11-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Citrulline GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-11-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Citrulline GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | 2021-11-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Citrulline GC-MS (TBDMS_1_3) - 70eV, Positive | Not Available | 2021-11-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Citrulline GC-MS (TBDMS_1_4) - 70eV, Positive | Not Available | 2021-11-06 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - Citrulline Quattro_QQQ 10V, Positive-QTOF (Annotated) | splash10-0a4i-0900000000-4c1d7af748a47e489949 | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Citrulline Quattro_QQQ 25V, Positive-QTOF (Annotated) | splash10-00di-9000000000-988fced362fc0da157c9 | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Citrulline Quattro_QQQ 40V, Positive-QTOF (Annotated) | splash10-00di-9000000000-0818e0e8bcee12692498 | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Citrulline LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOF | splash10-004j-0900000000-5fa8a338dcd2f2a6bdd2 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Citrulline LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOF | splash10-004i-0900000000-16763200aa07f7629ad4 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Citrulline LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOF | splash10-03di-3900000000-d9cfc5187aa799f6f978 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Citrulline LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOF | splash10-0a4i-0900000000-10ee9a593e13550bec1c | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Citrulline LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOF | splash10-004i-0900000000-45d272576af34c9512a3 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Citrulline LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOF | splash10-014i-3900000000-6177a284fdea5a3f1306 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Citrulline LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOF | splash10-0a4i-0900000000-d9456d45e2dbd7a3df10 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Citrulline LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOF | splash10-004i-0900000000-ada57cdc73bda93be483 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Citrulline LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOF | splash10-008a-0904000000-23fbe48f82e515087d68 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Citrulline LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOF | splash10-03di-5900000000-78afcbaf8b8b3eabf174 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Citrulline LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOF | splash10-001i-0900000000-8fb191d4c20fd54b9282 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Citrulline LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOF | splash10-00di-0900000000-da484f0362a8dca5127e | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Citrulline LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOF | splash10-00e9-0900000000-46229b4f77feabb3f857 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Citrulline LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOF | splash10-001i-0900000000-4aca1022c393602a297d | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Citrulline LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOF | splash10-001i-0900000000-3bc2eff2e907b7734cc8 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Citrulline LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOF | splash10-001i-3900000000-2613bf40e3be814da86f | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Citrulline LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOF | splash10-0006-9300000000-e83287bbc060eb9cf6f3 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Citrulline LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOF | splash10-056r-0900000000-694a8872bdfd7eec1f2b | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Citrulline LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOF | splash10-08fr-2900000000-15b4711991ea9985fb2b | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Citrulline LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOF | splash10-00di-9300000000-915fbb73e0b728420e4a | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Citrulline LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOF | splash10-00di-9000000000-67e60567f5c062728350 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Citrulline LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOF | splash10-00di-9000000000-25140713431edd7c5eea | 2012-08-31 | HMDB team, MONA | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Experimental 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | 2012-12-04 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Experimental 1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, experimental) | 2021-10-10 | Wishart Lab | View Spectrum | Experimental 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | 2012-12-05 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-03 | FELIX lab | View Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | - Blood
- Cerebrospinal Fluid (CSF)
- Feces
- Saliva
- Sweat
- Urine
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Tissue Locations | - Bladder
- Epidermis
- Fibroblasts
- Intestine
- Kidney
- Liver
- Neuron
- Placenta
- Platelet
- Prostate
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | 10-60 uM | Infant (0-1 year old) | Not Specified | Normal | | details | Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 6-40 uM | Newborn (0-30 days old) | Both | Normal | | details | Blood | Detected and Quantified | 6-60 uM | Infant (1 - 3 months old) | Both | Normal | | details | Blood | Detected and Quantified | 8-70 uM | Children (3 months - 6 years old) | Both | Normal | | details | Blood | Detected and Quantified | 10-70 uM | Children (6 - 18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 19-51 uM | Infant (0-1 year old) | Male | Normal | | details | Blood | Detected and Quantified | 38.0 (30.0-46.0) uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 19-33 uM | Infant (0-1 year old) | Not Specified | Normal | | details | Blood | Detected and Quantified | <43 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 8-47 uM | Newborn (0-30 days old) | Not Specified | Normal | | details | Blood | Detected and Quantified | 10-45 uM | Infant (0-1 year old) | Not Specified | Normal | | details | Blood | Detected and Quantified | 10-50 uM | Children (1 - 13 years old) | Both | Normal | | details | Blood | Detected and Quantified | 16 +/- 5 uM | Infant (0-1 year old) | Both | Normal | | details | Blood | Detected and Quantified | 29.8 +/- 7.91 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 35 +/- 10 uM | Adult (>18 years old) | Female | Normal | | details | Blood | Detected and Quantified | 31 +/- 8 uM | Children (1 - 13 years old) | Female | Normal | | details | Blood | Detected and Quantified | 20.4(16.7-26.3) uM | Children (1-13 uears old) | Both | Normal | | details | Blood | Detected and Quantified | 36.0 +/- 8.0 uM | Children (1-13 years old) | Male | Normal | | details | Blood | Detected and Quantified | 37.0 +/- 9.0 uM | Adult (>18 years old) | Male | Normal | | details | Blood | Detected and Quantified | 35.0 +/- 10.0 uM | Adult (>18 years old) | Female | Normal | | details | Blood | Detected and Quantified | 37 +/- 9 uM | Adult (>18 years old) | Male | Normal | | details | Blood | Detected and Quantified | 38.0 (30.0-46.0) uM | Adult (>18 years old) | Not Specified | Normal | | details | Blood | Detected and Quantified | 15.0-45.0 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 26 uM | Children (1-13 years old) | Not Specified | Normal | | details | Blood | Detected and Quantified | 5-37 uM | Newborn (0-30 days old) | Not Specified | Normal | | details | Blood | Detected and Quantified | 10-60 uM | Children (1-13 years old) | Not Specified | Normal | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 2.8 +/- 1.0 uM | Adult (>18 years old) | Male | Normal | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 2.8 +/- 1.8 uM | Adult (>18 years old) | Not Specified | Normal | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 2.62 (1.35-3.89) uM | Adult (>18 years old) | Both | Normal | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 5.81+/- 1.23 uM | Adult (>18 years old) | Both | Normal | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 0-4.4 uM | Children (0 - 10 years old) | Both | Normal | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 0-4.5 uM | Adolescent (>11 years old) | Both | Normal | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 1.5 +/- 0.5 uM | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Children (6 - 18 years old) | Not Specified | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected and Quantified | 340 +/- 270 nmol/g wet feces | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected and Quantified | 70 +/- 50 nmol/g wet feces | Adult (>18 years old) | Both | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Saliva | Detected and Quantified | 25.30 +/- 19.00 uM | Adult (>18 years old) | Female | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected and Quantified | 8.1 +/- 0.94 uM | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected and Quantified | 8.1 +/- 1.4 uM | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected and Quantified | 26.2 +/- 33.1 uM | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected and Quantified | 9.2 +/- 2.1 uM | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected and Quantified | 51.82 +/- 64.25 uM | Adult (>18 years old) | Both | Normal | | details | Saliva | Detected and Quantified | 6.8 +/- 4.1 uM | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected and Quantified | 4.61 +/- 2.82 uM | Adult (>18 years old) | Female | Normal | | details | Sweat | Detected and Quantified | < 10 uM | Adult (60 years old) | Male | Normal | | details | Sweat | Detected and Quantified | < 10 uM | Adult (40 years old) | Male | Normal | | details | Urine | Detected and Quantified | <1.018 umol/mmol creatinine | Children (1-13 years old) | Not Specified | Normal | | details | Urine | Detected and Quantified | 1.08 (0.065-2.1) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0.19 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 7.91 +/- 7.91 umol/mmol creatinine | Newborn (0-30 days old) | Both | Normal | | details | Urine | Detected and Quantified | 21.48 +/- 16.96 umol/mmol creatinine | Newborn (0-30 days old) | Both | Normal | | details | Urine | Detected and Quantified | 40.70 +/- 30.53 umol/mmol creatinine | Newborn (0-30 days old) | Both | Normal | | details | Urine | Detected and Quantified | <1.58 umol/mmol creatinine | Adolescent (13-18 years old) | Not Specified | Normal | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0.00-74.25 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0-16.507 umol/mmol creatinine | Infant (0-1 year old) | Not Specified | Normal | | details | Urine | Detected and Quantified | <1.36 umol/mmol creatinine | Adult (>18 years old) | Not Specified | Normal | | details | Urine | Detected and Quantified | <8.14 umol/mmol creatinine | Infant (0-1 year old) | Not Specified | Normal | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0.50 +/- 0.54 umol/mmol creatinine | Children (1-13 years old) | Male | Normal | - Geigy Scientific ...
- West Cadwell, N.J...
- Basel, Switzerlan...
| details | Urine | Detected and Quantified | 1.1 +/- 0.84 umol/mmol creatinine | Adult (>18 years old) | Male | Normal | - Geigy Scientific ...
- West Cadwell, N.J...
- Basel, Switzerlan...
| details | Urine | Detected and Quantified | 0.99 +/- 0.69 umol/mmol creatinine | Adult (>18 years old) | Female | Normal | - Geigy Scientific ...
- West Cadwell, N.J...
- Basel, Switzerlan...
| details | Urine | Detected and Quantified | 1.81 (1.26-3.21) umol/mmol creatinine | Newborn (0-30 days old) | Both | Normal | | details | Urine | Detected and Quantified | <6.45 umol/mmol creatinine | Children (1-13 years old) | Not Specified | Normal | | details | Urine | Detected and Quantified | 0.24 +/- 0.23 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0.8 (0.2-1.7) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 28.753 +/- 22.885 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Normal | | details | Urine | Detected and Quantified | 0 - 10.97 umol/mmol creatinine | Newborn (0-30 days old) | Both | Normal | | details | Urine | Detected and Quantified | 0 - 9.95 umol/mmol creatinine | Infant (1 - 6 months old) | Both | Normal | | details | Urine | Detected and Quantified | 0 - 8.03 umol/mmol creatinine | Infant (6 months - <1 year old) | Both | Normal | | details | Urine | Detected and Quantified | 0 - 7.01 umol/mmol creatinine | Children (1 - 2 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0 - 5.99 umol/mmol creatinine | Children (2 - 4 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0 - 4.97 umol/mmol creatinine | Children (4 - 13 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0 - 3.96 umol/mmol creatinine | Adolescent (13 - 21 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0 - 3.96 umol/mmol creatinine | Adult (>21 years old) | Both | Normal | | details | Urine | Detected and Quantified | 1.4114 +/- 1.0599 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Normal | | details | Urine | Detected and Quantified | <1.58 umol/mmol creatinine | Children (1-13 years old) | Not Specified | Normal | | details | Urine | Detected and Quantified | 0-10 umol/mmol creatinine | Infant (0-1 year old) | Both | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected and Quantified | 15 uM | Children (1-13 years old) | Male | Pearson Syndrome | | details | Blood | Detected and Quantified | 2 uM | Infant (0-1 year old) | Female | Pearson Syndrome | | details | Blood | Detected and Quantified | 284 uM | Infant (0-1 year old) | Male | Argininosuccinic aciduria (ASL) | | details | Blood | Detected and Quantified | 27.5 (10.0-45.0) uM | Adult (>18 years old) | Both | Argininosuccinic aciduria | | details | Blood | Detected and Quantified | 200.0 (100.0-300.0) uM | Children (1-13 years old) | Both | Argininosuccinic aciduria (ASL) | | details | Blood | Detected and Quantified | 13.0 (6.0-20.0) uM | Adult (>18 years old) | Both | Permanent intestinal failure | | details | Blood | Detected and Quantified | 25.4 (23.4-27.4) uM | Adult (>18 years old) | Both | Acute seizures | | details | Blood | Detected and Quantified | 26.8 (25.4-28.2) uM | Adult (>18 years old) | Both | Epilepsy | | details | Blood | Detected and Quantified | 26.9 (25.2-28.6) uM | Children (1-13 years old) | Both | Epilepsy | | details | Blood | Detected and Quantified | 13 uM | Newborn (0-30 days old) | Male | Narp Syndrome | | details | Blood | Detected and Quantified | 3-5 uM | Children (1-13 years old) | Male | Narp Syndrome | | details | Blood | Detected and Quantified | 0-19 uM | Infant (0-1 year old) | Both | Narp Syndrome | | details | Blood | Detected and Quantified | 86-1542 uM | Adult (>18 years old) | Both | Citrullinemia type II, adult-onset | | details | Blood | Detected and Quantified | 6-21 uM | Children (1-13 years old) | Both | Phosphoenolpyruvate Carboxykinase Deficiency 1, Cytosolic | | details | Blood | Detected and Quantified | 5 uM | Newborn (0-30 days old) | Male | Phosphoenolpyruvate Carboxykinase Deficiency 1, Cytosolic | | details | Blood | Detected and Quantified | 20.3(16.1-26.6) uM | Children (1-13 uears old) | Both | Environmental enteric dysfunction | | details | Blood | Detected and Quantified | 181 uM | Infant (0-1 year old) | Male | Fumaric aciduria | | details | Blood | Detected and Quantified | 0-7 uM | Newborn (0-30 days old) | Male | N-Acetylglutamate synthetase deficiency | | details | Blood | Detected and Quantified | 13-23 uM | Infant (0-1 year old) | Male | N-Acetylglutamate synthetase deficiency | | details | Blood | Detected and Quantified | 152-2752 uM | Children (1 - 13 years old) | Both | Citrullinemia Type I | | details | Blood | Detected and Quantified | 94.97 +/- 11.18 uM | Elderly (>65 years old) | Both | Alzheimer's disease | | details | Blood | Detected and Quantified | 28(0-275) uM | Children (1-13 years old) | Female | Pearson Syndrome | | details | Blood | Detected and Quantified | 286-485 uM | Newborn (0-30 days old) | Both | Citrullinemia type II, neonatal-onset | | details | Blood | Detected and Quantified | 6 +/- 5 uM | Children (1-13 years old) | Both | Cutis laxa, autosomal recessive, type IIIA | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 27.0 +/- 2.6 uM | Adult (>18 years old) | Both | Alzheimer's disease | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 5.38 +/- 0.94 uM | Adult (>18 years old) | Both | Schizophrenia | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Gout | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal cancer | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Female | ankylosing spondylitis | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Female | rheumatoid arthritis | | details | Feces | Detected but not Quantified | Not Quantified | Children (6 - 18 years old) | Not Specified | Crohns disease | | details | Feces | Detected but not Quantified | Not Quantified | Children (6 - 18 years old) | Not Specified | Ulcerative colitis | | details | Feces | Detected but not Quantified | Not Quantified | Children (6 - 18 years old) | Not Specified | Unclassified IBD | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal Cancer | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal Cancer | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Oral cancer | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Female | Breast cancer | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Not Specified | Pancreatic cancer | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Not Specified | Periodontal diseases | | details | Saliva | Detected and Quantified | 17.64 +/- 10.31 uM | Adult (>18 years old) | Male | Alzheimer's disease | | details | Saliva | Detected and Quantified | 17.48 +/- 14.00 uM | Adult (>18 years old) | Male | Frontotemporal lobe dementia | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Attachment loss | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Missing teeth | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Periodontal Probing Depth | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Tooth Decay | | details | Saliva | Detected and Quantified | 14.67 +/- 10.99 uM | Adult (>18 years old) | Both | Lewy body disease | | details | Urine | Detected and Quantified | 63.800-549.400 umol/mmol creatinine | Infant (0-1 year old) | Not Specified | Fumaric aciduria | | details | Urine | Detected and Quantified | 21.0 +/- 2.8 umol/mmol creatinine | Adult (>18 years old) | Both | Alzheimer's disease | | details | Urine | Detected and Quantified | 11.851 +/- 17.07 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Eosinophilic esophagitis | | details | Urine | Detected and Quantified | 1.2423 +/- 1.4785 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Eosinophilic esophagitis | | details | Urine | Detected and Quantified | 1.0274 +/- 0.8653 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Gastroesophageal reflux disease | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Bladder cancer | | details |
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Associated Disorders and Diseases |
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Disease References | Intestinal failure |
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- Crenn P, Coudray-Lucas C, Thuillier F, Cynober L, Messing B: Postabsorptive plasma citrulline concentration is a marker of absorptive enterocyte mass and intestinal failure in humans. Gastroenterology. 2000 Dec;119(6):1496-505. [PubMed:11113071 ]
| Epilepsy |
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- Rainesalo S, Keranen T, Palmio J, Peltola J, Oja SS, Saransaari P: Plasma and cerebrospinal fluid amino acids in epileptic patients. Neurochem Res. 2004 Jan;29(1):319-24. [PubMed:14992292 ]
| Alzheimer's disease |
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- Fonteh AN, Harrington RJ, Tsai A, Liao P, Harrington MG: Free amino acid and dipeptide changes in the body fluids from Alzheimer's disease subjects. Amino Acids. 2007 Feb;32(2):213-24. Epub 2006 Oct 10. [PubMed:17031479 ]
- Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
| Argininosuccinic aciduria |
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- Kleijer WJ, Garritsen VH, Linnebank M, Mooyer P, Huijmans JG, Mustonen A, Simola KO, Arslan-Kirchner M, Battini R, Briones P, Cardo E, Mandel H, Tschiedel E, Wanders RJ, Koch HG: Clinical, enzymatic, and molecular genetic characterization of a biochemical variant type of argininosuccinic aciduria: prenatal and postnatal diagnosis in five unrelated families. J Inherit Metab Dis. 2002 Sep;25(5):399-410. [PubMed:12408190 ]
- G.Frauendienst-Egger, Friedrich K. Trefz (2017). MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de). METAGENE consortium.
| Fumarase deficiency |
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- Allegri G, Fernandes MJ, Scalco FB, Correia P, Simoni RE, Llerena JC Jr, de Oliveira ML: Fumaric aciduria: an overview and the first Brazilian case report. J Inherit Metab Dis. 2010 Aug;33(4):411-9. doi: 10.1007/s10545-010-9134-2. Epub 2010 Jun 15. [PubMed:20549362 ]
| N-acetylglutamate synthetase deficiency |
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- Guffon N, Vianey-Saban C, Bourgeois J, Rabier D, Colombo JP, Guibaud P: A new neonatal case of N-acetylglutamate synthase deficiency treated by carbamylglutamate. J Inherit Metab Dis. 1995;18(1):61-5. [PubMed:7623444 ]
| Citrullinemia type I |
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- Kose E, Unal O, Bulbul S, Gunduz M, Haberle J, Arslan N: Identification of three novel mutations in fourteen patients with citrullinemia type 1. Clin Biochem. 2017 Aug;50(12):686-689. doi: 10.1016/j.clinbiochem.2017.01.011. Epub 2017 Jan 27. [PubMed:28132756 ]
| Citrullinemia type II, adult-onset |
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- Komatsu M, Yazaki M, Tanaka N, Sano K, Hashimoto E, Takei Y, Song YZ, Tanaka E, Kiyosawa K, Saheki T, Aoyama T, Kobayashi K: Citrin deficiency as a cause of chronic liver disorder mimicking non-alcoholic fatty liver disease. J Hepatol. 2008 Nov;49(5):810-20. doi: 10.1016/j.jhep.2008.05.016. Epub 2008 Jun 10. [PubMed:18620775 ]
| Pearson Syndrome |
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- Crippa BL, Leon E, Calhoun A, Lowichik A, Pasquali M, Longo N: Biochemical abnormalities in Pearson syndrome. Am J Med Genet A. 2015 Mar;167A(3):621-8. doi: 10.1002/ajmg.a.36939. [PubMed:25691415 ]
| Citrullinemia type II, neonatal-onset |
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- Ohura T, Kobayashi K, Tazawa Y, Nishi I, Abukawa D, Sakamoto O, Iinuma K, Saheki T: Neonatal presentation of adult-onset type II citrullinemia. Hum Genet. 2001 Feb;108(2):87-90. [PubMed:11281457 ]
| Cutis laxa, autosomal recessive, type IIIA |
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- Baumgartner MR, Hu CA, Almashanu S, Steel G, Obie C, Aral B, Rabier D, Kamoun P, Saudubray JM, Valle D: Hyperammonemia with reduced ornithine, citrulline, arginine and proline: a new inborn error caused by a mutation in the gene encoding delta(1)-pyrroline-5-carboxylate synthase. Hum Mol Genet. 2000 Nov 22;9(19):2853-8. [PubMed:11092761 ]
| Myopathy, lactic acidosis, and sideroblastic anemia 1 |
---|
- Parfait B, de Lonlay P, von Kleist-Retzow JC, Cormier-Daire V, Chretien D, Rotig A, Rabier D, Saudubray JM, Rustin P, Munnich A: The neurogenic weakness, ataxia and retinitis pigmentosa (NARP) syndrome mtDNA mutation (T8993G) triggers muscle ATPase deficiency and hypocitrullinaemia. Eur J Pediatr. 1999 Jan;158(1):55-8. [PubMed:9950309 ]
| Phosphoenolpyruvate Carboxykinase Deficiency 1, Cytosolic |
---|
- Vieira P, Cameron J, Rahikkala E, Keski-Filppula R, Zhang LH, Santra S, Matthews A, Myllynen P, Nuutinen M, Moilanen JS, Rodenburg RJ, Rolfs A, Uusimaa J, van Karnebeek CDM: Novel homozygous PCK1 mutation causing cytosolic phosphoenolpyruvate carboxykinase deficiency presenting as childhood hypoglycemia, an abnormal pattern of urine metabolites and liver dysfunction. Mol Genet Metab. 2017 Apr;120(4):337-341. doi: 10.1016/j.ymgme.2017.02.003. Epub 2017 Feb 6. [PubMed:28216384 ]
- Santra S, Cameron JM, Shyr C, Zhang L, Drogemoller B, Ross CJ, Wasserman WW, Wevers RA, Rodenburg RJ, Gupte G, Preece MA, van Karnebeek CD: Cytosolic phosphoenolpyruvate carboxykinase deficiency presenting with acute liver failure following gastroenteritis. Mol Genet Metab. 2016 May;118(1):21-7. doi: 10.1016/j.ymgme.2016.03.001. Epub 2016 Mar 4. [PubMed:26971250 ]
| Schizophrenia |
---|
- Do KQ, Lauer CJ, Schreiber W, Zollinger M, Gutteck-Amsler U, Cuenod M, Holsboer F: gamma-Glutamylglutamine and taurine concentrations are decreased in the cerebrospinal fluid of drug-naive patients with schizophrenic disorders. J Neurochem. 1995 Dec;65(6):2652-62. [PubMed:7595563 ]
| Colorectal cancer |
---|
- Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
- Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
- Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
| Crohn's disease |
---|
- Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
| Ulcerative colitis |
---|
- Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
| Gout |
---|
- Shao T, Shao L, Li H, Xie Z, He Z, Wen C: Combined Signature of the Fecal Microbiome and Metabolome in Patients with Gout. Front Microbiol. 2017 Feb 21;8:268. doi: 10.3389/fmicb.2017.00268. eCollection 2017. [PubMed:28270806 ]
| Rheumatoid arthritis |
---|
- Tie-juan ShaoZhi-xing HeZhi-jun XieHai-chang LiMei-jiao WangCheng-ping Wen. Characterization of ankylosing spondylitis and rheumatoid arthritis using 1H NMR-based metabolomics of human fecal extracts. Metabolomics. April 2016, 12:70 [Link]
| Perillyl alcohol administration for cancer treatment |
---|
- Sugimoto M, Wong DT, Hirayama A, Soga T, Tomita M: Capillary electrophoresis mass spectrometry-based saliva metabolomics identified oral, breast and pancreatic cancer-specific profiles. Metabolomics. 2010 Mar;6(1):78-95. Epub 2009 Sep 10. [PubMed:20300169 ]
| Pancreatic cancer |
---|
- Sugimoto M, Wong DT, Hirayama A, Soga T, Tomita M: Capillary electrophoresis mass spectrometry-based saliva metabolomics identified oral, breast and pancreatic cancer-specific profiles. Metabolomics. 2010 Mar;6(1):78-95. Epub 2009 Sep 10. [PubMed:20300169 ]
| Periodontal disease |
---|
- Sugimoto M, Wong DT, Hirayama A, Soga T, Tomita M: Capillary electrophoresis mass spectrometry-based saliva metabolomics identified oral, breast and pancreatic cancer-specific profiles. Metabolomics. 2010 Mar;6(1):78-95. Epub 2009 Sep 10. [PubMed:20300169 ]
| Frontotemporal dementia |
---|
- Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
| Lewy body disease |
---|
- Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
| Attachment loss |
---|
- Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
| Missing teeth |
---|
- Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
| Periodontal Probing Depth |
---|
- Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
| Tooth Decay |
---|
- Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
| Eosinophilic esophagitis |
---|
- Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
|
|
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Associated OMIM IDs | - 104300 (Alzheimer's disease)
- 207900 (Argininosuccinic aciduria)
- 606812 (Fumarase deficiency)
- 608300 (N-acetylglutamate synthetase deficiency)
- 215700 (Citrullinemia type I)
- 603471 (Citrullinemia type II, adult-onset)
- 557000 (Pearson Syndrome)
- 605814 (Citrullinemia type II, neonatal-onset)
- 219150 (Cutis laxa, autosomal recessive, type IIIA)
- 600462 (Myopathy, lactic acidosis, and sideroblastic anemia 1)
- 261680 (Phosphoenolpyruvate Carboxykinase Deficiency 1, Cytosolic)
- 181500 (Schizophrenia)
- 114500 (Colorectal cancer)
- 266600 (Crohn's disease)
- 138900 (Gout)
- 180300 (Rheumatoid arthritis)
- 260350 (Pancreatic cancer)
- 170650 (Periodontal disease)
- 600274 (Frontotemporal dementia)
- 610247 (Eosinophilic esophagitis)
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External Links |
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DrugBank ID | DB00155 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB011841 |
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KNApSAcK ID | C00001348 |
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Chemspider ID | 9367 |
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KEGG Compound ID | C00327 |
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BioCyc ID | L-CITRULLINE |
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BiGG ID | 34627 |
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Wikipedia Link | Citrulline |
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METLIN ID | 16 |
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PubChem Compound | 9750 |
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PDB ID | Not Available |
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ChEBI ID | 16349 |
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Food Biomarker Ontology | Not Available |
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VMH ID | CITR_L |
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MarkerDB ID | MDB00000279 |
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Good Scents ID | Not Available |
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References |
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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. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
- Engelborghs S, Marescau B, De Deyn PP: Amino acids and biogenic amines in cerebrospinal fluid of patients with Parkinson's disease. Neurochem Res. 2003 Aug;28(8):1145-50. [PubMed:12834252 ]
- Hagenfeldt L, Bjerkenstedt L, Edman G, Sedvall G, Wiesel FA: Amino acids in plasma and CSF and monoamine metabolites in CSF: interrelationship in healthy subjects. J Neurochem. 1984 Mar;42(3):833-7. [PubMed:6198473 ]
- Cynober LA: Plasma amino acid levels with a note on membrane transport: characteristics, regulation, and metabolic significance. Nutrition. 2002 Sep;18(9):761-6. [PubMed:12297216 ]
- Rainesalo S, Keranen T, Palmio J, Peltola J, Oja SS, Saransaari P: Plasma and cerebrospinal fluid amino acids in epileptic patients. Neurochem Res. 2004 Jan;29(1):319-24. [PubMed:14992292 ]
- Le Boucher J, Charret C, Coudray-Lucas C, Giboudeau J, Cynober L: Amino acid determination in biological fluids by automated ion-exchange chromatography: performance of Hitachi L-8500A. Clin Chem. 1997 Aug;43(8 Pt 1):1421-8. [PubMed:9267323 ]
- Crenn P, Coudray-Lucas C, Thuillier F, Cynober L, Messing B: Postabsorptive plasma citrulline concentration is a marker of absorptive enterocyte mass and intestinal failure in humans. Gastroenterology. 2000 Dec;119(6):1496-505. [PubMed:11113071 ]
- Melis GC, Boelens PG, van der Sijp JR, Popovici T, De Bandt JP, Cynober L, van Leeuwen PA: The feeding route (enteral or parenteral) affects the plasma response of the dipetide Ala-Gln and the amino acids glutamine, citrulline and arginine, with the administration of Ala-Gln in preoperative patients. Br J Nutr. 2005 Jul;94(1):19-26. [PubMed:16115328 ]
- DeLong GR, Glick TH: Ammonia metabolism in Reye syndrome and the effect of citrulline. Ann Neurol. 1982 Jan;11(1):53-8. [PubMed:7059128 ]
- Jianfeng G, Weiming Z, Ning L, Fangnan L, Li T, Nan L, Jieshou L: Serum citrulline is a simple quantitative marker for small intestinal enterocytes mass and absorption function in short bowel patients. J Surg Res. 2005 Aug;127(2):177-82. [PubMed:15921697 ]
- Liappis N, Pohl B, Weber HP, el-Karkani H: [Free amino acids in the saliva of children with phenylketonuria]. Klin Padiatr. 1986 Jan-Feb;198(1):25-8. [PubMed:3959486 ]
- Fleisher LD, Harris CJ, Mitchell DA, Nadler HL: Citrullinemia: prenatal diagnosis of an affected fetus. Am J Hum Genet. 1983 Jan;35(1):85-90. [PubMed:6823975 ]
- Potter MA, Zeesman S, Brennan B, Kobayashi K, Gao HZ, Tabata A, Saheki T, Whelan DT: Pregnancy in a healthy woman with untreated citrullinemia. Am J Med Genet A. 2004 Aug 15;129A(1):77-82. [PubMed:15266621 ]
- Wheatley DN, Kilfeather R, Stitt A, Campbell E: Integrity and stability of the citrulline-arginine pathway in normal and tumour cell lines. Cancer Lett. 2005 Sep 28;227(2):141-52. [PubMed:16112417 ]
- Reparon-Schuijt CC, van Esch WJ, van Kooten C, Schellekens GA, de Jong BA, van Venrooij WJ, Breedveld FC, Verweij CL: Secretion of anti-citrulline-containing peptide antibody by B lymphocytes in rheumatoid arthritis. Arthritis Rheum. 2001 Jan;44(1):41-7. [PubMed:11212174 ]
- Maruyama H, Ogawa M, Nishio T, Kobayashi K, Saheki T, Sunohara N: Citrullinemia type II in a 64-year-old man with fluctuating serum citrulline levels. J Neurol Sci. 2001 Jan 1;182(2):167-70. [PubMed:11137523 ]
- McLaurin J, Moscarello MA: The preparation of antibodies reactive against citrulline-containing charge isomers of myelin basic protein but not against the arginine-containing charge isomers. Anal Biochem. 1990 Dec;191(2):272-7. [PubMed:1707596 ]
- Facchinetti F, Longo M, Piccinini F, Neri I, Volpe A: L-arginine infusion reduces blood pressure in preeclamptic women through nitric oxide release. J Soc Gynecol Investig. 1999 Jul-Aug;6(4):202-7. [PubMed:10486782 ]
- Origuchi Y, Ushijima T, Sakaguchi M, Akaboshi I, Matsuda I: Citrullinemia presenting as uncontrollable epilepsy. Brain Dev. 1984;6(3):328-31. [PubMed:6486381 ]
- Booth FA, Haworth JC, Dilling LA, Perry TL, Greenberg CR, Seargeant LE, Penn AM, Rhead WJ: Mitochondrial encephalomyopathy with associated aminoacidopathy in a male sibship. J Pediatr. 1989 Jul;115(1):81-8. [PubMed:2738799 ]
- Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19. [PubMed:29457794 ]
- Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
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