Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:05:54 UTC |
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Update date | 2019-11-26 02:59:28 UTC |
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Primary ID | FDB003654 |
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Secondary Accession Numbers | |
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Chemical Information |
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FooDB Name | Ornithine |
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Description | A non-essential and nonprotein amino acid, ornithine is critical for the production of the body's proteins, enzymes and muscle tissue. Ornithine plays a central role in the urea cycle and is important for the disposal of excess nitrogen (ammonia). Ornithine is the starting point for the synthesis of many polyamines such as putrescine and spermine. Ornithine supplements are claimed to enhance the release of growth hormone and to burn excess body fat. Ornithine is necessary for proper immune function and good liver function.; AF112968; L-Ornithine is one of the products of the action of the enzyme arginase on L-arginine, creating urea. Therefore, ornithine is a central part of the urea cycle, which allows for the disposal of excess nitrogen. Ornithine is recycled and in a manner is a catalyst. First, ammonia is converted into carbamoyl phosphate (phosphate-CONH2), which creates one half of urea. Ornithine is converted into a urea derivative at the ? (terminal) nitrogen by carbamoyl phosphate. Another nitrogen is added from aspartate, producing the denitrogenated fumarate, and the resulting arginine (a guanidinium compound) is hydrolysed back to ornithine, producing urea. The nitrogens of urea come from the ammonia and aspartate, and the nitrogen in ornithine remains intact.; ORNT1). Mutations in the mitochondrial ornithine transporter result in hyperammonemia, hyperornithinemia, homocitrullinuria (HHH) syndrome, a disorder of the urea cycle. (PMID 16256388) The pathophysiology of the disease may involve diminished ornithine transport into mitochondria, resulting in ornithine accumulation in the cytoplasm and reduced ability to clear carbamoyl phosphate and ammonia loads. (OMIM 838970); Ornithine is an amino acid produced in the urea cycle by the splitting off of urea from arginine. It is a central part of the urea cycle, which allows for the disposal of excess nitrogen. L-Ornithine is also a precursor of citrulline and arginine. In order for ornithine produced in the cytosol to be converted to citrulline, it must first cross the inner mitochondrial membrane into the mitochondrial matrix where it is carbamylated by ornithine transcarbamylase. This transfer is mediated by the mitochondrial ornithine transporter (SLC25A15; Ornithine is an amino acid which plays a role in the urea cycle. Ornithine is found in many foods, some of which are soft-necked garlic, orange bell pepper, sunburst squash (pattypan squash), and cucumber. |
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CAS Number | 3184-13-2 |
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Structure | |
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Synonyms | Synonym | Source |
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2,5-Diaminopentanoic acid | ChEBI | 2,5-Diaminovaleric acid | ChEBI | DL-Ornithine | ChEBI | Orn | ChEBI | 2,5-Diaminopentanoate | Kegg | 2,5-Diaminovalerate | Generator | L-Ornithine monochlorohydric acid/ornithine | Generator | (+/-)-2,5-diaminopentanoic acid monohydrochloride | HMDB | 2,5-Diaminopentanoic acid hydrochloride | HMDB | D -2,5-Diaminopentanoic acid | HMDB | D-Ornithine | HMDB | DL -2,5-Diaminopentanoic acid | HMDB | DL-Ornithine HCL | HMDB | DL-Ornithine monohydrochloride | HMDB | DL-Ornithine, hydrochloride | HMDB | L -2,5-Diaminopentanoic acid | HMDB | L-Ornithine hydrochloride | HMDB | L-Ornithine monohydrochloride | HMDB | L-Ornithine, monohydrochloride | HMDB | L-Ornithine-carboxy-14C hydrochloride | HMDB | MonohydrochlorideDL-ornithine | HMDB | Monohydrochloridel-ornithine | HMDB | Ornithine DL-form HCL | HMDB | Ornithine DL-form monohydrochloride | HMDB | Ornithine hydrochloride | HMDB | Ornithine monohydrochloride | HMDB | Ornithine, hydrochloride (1:1) | HMDB | Ornithine, monohydrochloride | HMDB | Poly-L-ornithine hydrochloride | HMDB | Ornithine sulfate (1:1), (L)-isomer | MeSH | Ornithine hydrochloride, (D)-isomer | MeSH | Ornithine monohydrochloride, (DL)-isomer | MeSH | Ornithine, (L)-isomer | MeSH | Ornithine hydrochloride, (L)-isomer | MeSH | Ornithine monohydrobromide, (L)-isomer | MeSH | Ornithine, (DL)-isomer | MeSH | Ornithine monohydrochloride, (D)-isomer | MeSH | 2,5 Diaminopentanoic acid | MeSH | Ornithine dihydrochloride, (L)-isomer | MeSH | Ornithine phosphate (1:1), (L)-isomer | MeSH | Ornithine hydrochloride, (DL)-isomer | MeSH | Ornithine monoacetate, (L)-isomer | MeSH | Ornithine, (D)-isomer | MeSH | (+)-s-ornithine | biospider | (2S)-2,5-diaminopentanoic acid | biospider | (S)-2,5-Diaminopentanoate | biospider | (S)-2,5-Diaminopentanoic acid | biospider | (S)-2,5-Diaminovalerate | Generator | (S)-2,5-diaminovaleric acid | biospider | (s)-a,d-diaminovalerate | biospider | (s)-a,d-diaminovaleric acid | biospider | (S)-a,delta-Diaminovalerate | Generator | (S)-a,delta-Diaminovaleric acid | Generator | (S)-a,δ-diaminovalerate | Generator | (S)-a,δ-diaminovaleric acid | Generator | (S)-alpha,delta-Diaminovalerate | Generator | (s)-alpha,delta-diaminovaleric acid | biospider | (s)-ornithine | biospider | (S)-α,δ-diaminovalerate | Generator | (S)-α,δ-diaminovaleric acid | Generator | 2,5-diaminopentanoate | biospider | 2,5-diaminopentanoic acid | biospider | 2,5-diaminovaleric acid | biospider | 5-amino-L-Norvaline | biospider | Alpha, delta-diaminovaleric acid | biospider | L-(-)-ornithine | biospider | L-Norvaline, 5-amino- | biospider | L-Ornithine | ChEBI | L-Ornithine (9CI) | biospider | Ornithine, L- (8CI) | biospider | Pentanoic acid, 2,5-diamino-, (S)- | biospider |
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Predicted Properties | |
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Chemical Formula | C5H12N2O2 |
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IUPAC name | 2,5-diaminopentanoic acid |
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InChI Identifier | InChI=1S/C5H12N2O2/c6-3-1-2-4(7)5(8)9/h4H,1-3,6-7H2,(H,8,9) |
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InChI Key | AHLPHDHHMVZTML-UHFFFAOYSA-N |
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Isomeric SMILES | NCCCC(N)C(O)=O |
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Average Molecular Weight | 132.161 |
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Monoisotopic Molecular Weight | 132.089877638 |
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Classification |
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Description | Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). |
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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 | Alpha amino acids |
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Alternative Parents | |
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Substituents | - Alpha-amino acid
- Fatty acid
- Amino acid
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Hydrocarbon derivative
- Organic oxygen compound
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Organic nitrogen compound
- Primary aliphatic amine
- Carbonyl group
- Amine
- Organopnictogen compound
- Organic oxide
- 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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Disposition | Source: Biological location: |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Not Available | |
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Mass Composition | Not Available | |
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Melting Point | 140 oC | |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | -4.22 | SANGSTER (1994) |
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Experimental pKa | 1.94 | |
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Isoelectric point | Not Available | |
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Charge | +1 | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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Predicted GC-MS | Ornithine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-001u-9000000000-deb45bcb4280a1e67a8f | Spectrum | Predicted GC-MS | Ornithine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0019-9100000000-67a994a61d82dc152d64 | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-01q9-8900000000-2e4d4d66936dd4f319b6 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - , negative | splash10-001i-0900000000-32310ed59a11fecc22ee | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - , negative | splash10-001i-0900000000-f961bdc91f8c937f8007 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-03xr-0900000000-aaa6fc0b534b5ae6a77f | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - , positive | splash10-00xr-8900000000-ff44915c48b3380e7423 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - , positive | splash10-00xr-8900000000-e4ce3191e51be8f7b59a | 2017-09-14 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-015i-9800000000-110d911afecf530f72fd | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00dr-9100000000-5fa5c7cc1ac450fca1d9 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00dl-9000000000-91631a0a6d3c31d893d5 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-1900000000-4d97ca74bc7987b5c724 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-01q9-6900000000-a4a407f12771e9b56e13 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00di-9000000000-7a4945316591ef8dd14a | 2015-05-27 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 6026 |
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ChEMBL ID | CHEMBL446143 |
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KEGG Compound ID | C00077 |
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Pubchem Compound ID | 6262 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 18257 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | DB00129 |
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HMDB ID | HMDB00214 |
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CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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EAFUS ID | Not Available |
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Dr. Duke ID | ORNITHINE |
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BIGG ID | 37976 |
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KNApSAcK ID | Not Available |
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HET ID | ORN |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Ornithine |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | |
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Enzymes | Name | Gene Name | UniProt ID |
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Glycine amidinotransferase, mitochondrial | GATM | P50440 | Ornithine aminotransferase, mitochondrial | OAT | P04181 | Ornithine decarboxylase | ODC1 | P11926 | Ornithine decarboxylase antizyme 1 | OAZ1 | P54368 | High affinity cationic amino acid transporter 1 | SLC7A1 | P30825 | Delta-1-pyrroline-5-carboxylate synthase | ALDH18A1 | P54886 | Ornithine carbamoyltransferase, mitochondrial | OTC | P00480 | Cationic amino acid transporter 4 | SLC7A4 | O43246 | Mitochondrial ornithine transporter 1 | SLC25A15 | Q9Y619 | Mitochondrial ornithine transporter 2 | SLC25A2 | Q9BXI2 | Low affinity cationic amino acid transporter 2 | SLC7A2 | P52569 | Ornithine decarboxylase antizyme 2 | OAZ2 | O95190 | Ornithine decarboxylase antizyme 3 | OAZ3 | Q9UMX2 | Antizyme inhibitor 1 | AZIN1 | O14977 |
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Pathways | |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
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