| Record Information |
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| Version | 2.0 |
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| Created at | 2005-11-16 15:48:42 UTC |
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| Updated at | 2022-02-06 02:12:16 UTC |
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| NP-MRD ID | NP0000119 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Ornithine |
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| Description | Ornithine or L-ornithine, also known as (S)-2,5-diaminopentanoic acid is a member of the class of compounds known as L-alpha-amino acids. L-alpha-amino acids are alpha amino acids which have the L-configuration of the alpha-carbon atom. L-ornithine is soluble (in water) and a moderately basic compound. Ornithine is a non-proteinogenic amino acid that plays a role in the urea cycle. It is considered to be a non-essential amino acid. A non-essential amino acid is an amino acid that can be synthesized from central metabolic pathway intermediates in humans and is not required in the diet. 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. Outside the human body, L-ornithine is abundant in a number of food items such as wild rice, brazil nuts, common oregano, and common grapes. L-ornithine can be found throughout most human tissues; and in most biofluids, some of which include blood, urine, cerebrospinal fluid (CSF), sweat, saliva, and feces. L-ornithine exists in all living species, from bacteria to plants to humans. L-Ornithine is also a precursor of citrulline and arginine. In order for ornithine that is 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 the enzyme known as ornithine transcarbamylase. This transfer is mediated by the mitochondrial ornithine transporter (SLC25A15; AF112968; 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 ). In humans, L-ornithine is involved in a number of other metabolic disorders, some of which include, ornithine transcarbamylase deficiency (OTC deficiency), argininemia, and guanidinoacetate methyltransferase deficiency (GAMT deficiency). Ornithine is abnormally accumulated in the body in ornithine transcarbamylase deficiency. Moreover, Ornithine is found to be associated with cystinuria, hyperdibasic aminoaciduria I, and lysinuric protein intolerance, which are inborn errors of metabolism. It has been claimed that ornithine improves athletic performance, has anabolic effects, has wound-healing effects, and is immuno-enhancing. |
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| Structure | 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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| 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 Mass | 132.1610 Da |
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| Monoisotopic Mass | 132.08988 Da |
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| IUPAC Name | (2S)-2,5-diaminopentanoic acid |
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| Traditional Name | ornithine |
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| CAS Registry Number | 3184-13-2 |
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| SMILES | NCCC[C@H](N)C(O)=O |
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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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| Experimental Spectra |
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| | Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, simulated) | Ahselim | | | 2022-02-06 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | Predicted Spectra |
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| Not Available | | Chemical Shift Submissions |
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| | Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, simulated) | varshavi.d26@gmail.com | Not Available | Not Available | 2021-07-25 | View Spectrum |
| | Species |
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| Species of Origin | |
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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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| 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, J. (1993). LOGKOW- a Databank of Evaluated Octanol-Water Partition Coefficients. Sangster Research Laboratories, Montreal. |
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| Predicted Properties | |
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| General References | - Peters T, Thaete C, Wolf S, Popp A, Sedlmeier R, Grosse J, Nehls MC, Russ A, Schlueter V: A mouse model for cystinuria type I. Hum Mol Genet. 2003 Sep 1;12(17):2109-20. [PubMed:12923163 ]
- Mayer UM: [Hyperornithinaemia in patients with retinal dystrophy]. Ophthalmologe. 2003 Jan;100(1):55-61. [PubMed:12557027 ]
- Gray RG, Green A, Hall S, McKeown C: Prenatal exclusion of the HHH syndrome. Prenat Diagn. 1995 May;15(5):474-6. [PubMed:7644438 ]
- Jensen TG, Sullivan DM, Morgan RA, Taichman LB, Nussenblatt RB, Blaese RM, Csaky KG: Retrovirus-mediated gene transfer of ornithine-delta-aminotransferase into keratinocytes from gyrate atrophy patients. Hum Gene Ther. 1997 Nov 20;8(17):2125-32. [PubMed:9414260 ]
- Sell DR, Monnier VM: Ornithine is a novel amino acid and a marker of arginine damage by oxoaldehydes in senescent proteins. Ann N Y Acad Sci. 2005 Jun;1043:118-28. [PubMed:16037230 ]
- Stadler S, Gempel K, Bieger I, Pontz BF, Gerbitz KD, Bauer MF, Hofmann S: Detection of neonatal argininosuccinate lyase deficiency by serum tandem mass spectrometry. J Inherit Metab Dis. 2001 Jun;24(3):370-8. [PubMed:11486903 ]
- Gokmen SS, Aygit AC, Ayhan MS, Yorulmaz F, Gulen S: Significance of arginase and ornithine in malignant tumors of the human skin. J Lab Clin Med. 2001 May;137(5):340-4. [PubMed:11329531 ]
- Morizono H, Woolston JE, Colombini M, Tuchman M: The use of yeast mitochondria to study the properties of wild-type and mutant human mitochondrial ornithine transporter. Mol Genet Metab. 2005 Dec;86(4):431-40. Epub 2005 Oct 26. [PubMed:16256388 ]
- Ansone L, Briviba M, Silamikelis I, Terentjeva A, Perkons I, Birzniece L, Rovite V, Rozentale B, Viksna L, Kolesova O, Klavins K, Klovins J: Amino Acid Metabolism is Significantly Altered at the Time of Admission in Hospital for Severe COVID-19 Patients: Findings from Longitudinal Targeted Metabolomics Analysis. Microbiol Spectr. 2021 Dec 22;9(3):e0033821. doi: 10.1128/spectrum.00338-21. Epub 2021 Dec 8. [PubMed:34878333 ]
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