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Record Information |
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Version | 1.0 |
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Creation Date | 2016-09-30 22:26:50 UTC |
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Update Date | 2020-06-04 20:49:03 UTC |
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BMDB ID | BMDB0000214 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Ornithine |
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Description | Ornithine, also known as (S)-ornithine, 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. Ornithine is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalance. it has been claimed that ornithine improves athletic performance, has anabolic effects, has wound-healing effects, and is immuno-enhancing. Ornithine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Ornithine exists in all living species, ranging from bacteria to humans. Ornithine participates in a number of enzymatic reactions, within cattle. In particular, Carbamoyl phosphate and ornithine can be converted into citrulline; which is mediated by the enzyme ornithine carbamoyltransferase, mitochondrial. In addition, Ornithine and urea can be biosynthesized from L-arginine; which is mediated by the enzyme arginase-1. In cattle, ornithine is involved in the metabolic pathway called the urea cycle pathway. Ornithine is a potentially toxic compound. |
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Structure | |
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Synonyms | Value | Source |
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(S)-2,5-Diaminopentanoate | ChEBI | (S)-2,5-Diaminopentanoic acid | ChEBI | (S)-2,5-Diaminovaleric acid | ChEBI | (S)-alpha,delta-Diaminovaleric acid | ChEBI | (S)-Ornithine | ChEBI | (S)-2,5-Diaminovalerate | Generator | (S)-a,delta-Diaminovalerate | Generator | (S)-a,delta-Diaminovaleric acid | Generator | (S)-alpha,delta-Diaminovalerate | Generator | (S)-Α,δ-diaminovalerate | Generator | (S)-Α,δ-diaminovaleric acid | Generator | (S)-a,Δ-diaminovalerate | HMDB | (S)-a,Δ-diaminovaleric acid | HMDB | (+)-S-Ornithine | HMDB | (S)-a,D-Diaminovalerate | HMDB | (S)-a,D-Diaminovaleric acid | HMDB | 5-Amino-L-norvaline | HMDB | L-(-)-Ornithine | HMDB | L-Ornithine | HMDB | 2,5-Diaminopentanoic acid | HMDB | Ornithine dihydrochloride, (L)-isomer | HMDB | Ornithine hydrochloride, (D)-isomer | HMDB | Ornithine, (D)-isomer | HMDB | Ornithine, (L)-isomer | HMDB | 2,5 Diaminopentanoic acid | HMDB | Ornithine monoacetate, (L)-isomer | HMDB | Ornithine monohydrochloride, (D)-isomer | HMDB | Ornithine monohydrochloride, (DL)-isomer | HMDB | Ornithine phosphate (1:1), (L)-isomer | HMDB | Ornithine sulfate (1:1), (L)-isomer | HMDB | Ornithine hydrochloride, (DL)-isomer | HMDB | Ornithine hydrochloride, (L)-isomer | HMDB | Ornithine monohydrobromide, (L)-isomer | HMDB | Ornithine, (DL)-isomer | HMDB |
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Chemical Formula | C5H12N2O2 |
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Average Molecular Weight | 132.161 |
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Monoisotopic Molecular Weight | 132.089877638 |
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IUPAC Name | Not Available |
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Traditional Name | Not Available |
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CAS Registry Number | 3184-13-2 |
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SMILES | Not Available |
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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)/t4-/m0/s1 |
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InChI Key | AHLPHDHHMVZTML-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
- Amino acid
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Amine
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Organic oxygen compound
- Primary aliphatic amine
- Organic nitrogen compound
- Carbonyl group
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Status | Detected and Quantified |
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Origin | |
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Biofunction | Not Available |
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Application | Not Available |
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Cellular locations | |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 140 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 620 mg/mL | Not Available | LogP | -4.22 | SANGSTER (1994) |
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Predicted Properties | Not Available |
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Spectra |
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Spectra | |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | - Blood
- Epidermis
- Intestine
- Liver
- Longissimus Thoracis Muscle
- Mammary Gland
- Milk
- Muscle
- Prostate Tissue
- Ruminal Fluid
- Semen
- Semimembranosus Muscle
- Testis
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | 61 +/- 13 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 80-98 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 55.3 uM | Not Specified | Both | Normal | | details | Blood | Detected and Quantified | 62-135 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 31-41 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 29-32 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Epidermis | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Intestine | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Liver | Detected and Quantified | 270 +/- 63 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Liver | Detected and Quantified | 984-1184 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Longissimus Thoracis Muscle | Detected and Quantified | 35 +/- 12 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 2 - 15 uM | Not Specified | Not Specified | Normal | | details | Muscle | Detected and Quantified | 80-187 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Prostate Tissue | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 149 +/- 77 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 17 +/- 7 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 25 +/- 12 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 38 +/- 13 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 19 +/- 12 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 19 +/- 12 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 16.4 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 25.4 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 58.7 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 15.9 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 15.96 +/- 14.89 uM | Not Specified | Not Specified | Normal | | details | Semen | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Semimembranosus Muscle | Detected and Quantified | 40 +/- 10 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Testis | Detected and Quantified | 10 +/- 3 nmol/g of tissue | Not Specified | Not Specified | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | All Mycobacterium avium subsp. paratuberculosis-infected | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | High dose Mycobacterium avium subsp. paratuberculosis-infected | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Low dose Mycobacterium avium subsp. paratuberculosis-infected | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Mycobacterium avium subsp. paratuberculosis infection | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Sub/clinical ketosis | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Heat stress | | details | Ruminal Fluid | Detected and Quantified | 58.74 +/- 27.62 uM | Not Specified | Not Specified | Rumen acidosis | | details |
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External Links |
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HMDB ID | HMDB0000214 |
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DrugBank ID | DB00129 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB030969 |
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KNApSAcK ID | C00001384 |
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Chemspider ID | 6026 |
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KEGG Compound ID | C00077 |
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BioCyc ID | L-ORNITHINE |
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BiGG ID | 37976 |
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Wikipedia Link | Ornithine |
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METLIN ID | 27 |
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PubChem Compound | 6262 |
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PDB ID | Not Available |
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ChEBI ID | 15729 |
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References |
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Synthesis Reference | Zhang, Peng; Zhang, Shurong; Liu, Chunqiao; Yang, Yuhong. Method for preparing L-ornithine by enzymatic conversion. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 8pp. |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563. [PubMed:20338431 ]
- Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30. [PubMed:25087032 ]
- Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15. [PubMed:23497994 ]
- Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]
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