Grundinformationen
- Standard-SMILES
NCCC[C@H](N)C(=O)O- InChIKey
AHLPHDHHMVZTML-BYPYZUCNSA-N- Summenformel
- C5H12N2O2
- Durchschnittliche Molmasse
- 132,16 g/mol
- Monoisotopische Masse
- 132,08987762
Überblick
L-ornithine is an optically active form of ornithine having L-configuration. It has a role as a hepatoprotective agent, a mouse metabolite and an algal metabolite. It is an ornithine and a non-proteinogenic L-alpha-amino acid. It is a conjugate base of a L-ornithinium(1+). It is a conjugate acid of a L-ornithinate. It is an enantiomer of a D-ornithine.
Namen und Bezeichner
- Bevorzugter Name
- L-(-)-Ornithine
- IUPAC
- (2S)-2,5-diaminopentanoic acid
- Englischer Name
- polyornithine
- Summenformel
- C5H12N2O2
- Molmasse
- 132.16098
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
25104-12-5、3184-13-2、70-26-8- PubChem CID
- 6262
- DTXSID
DTXSID00883219- ChEMBL
CHEMBL446143- ChEBI
CHEBI:15729- UNII
- E524N2IXA3
- EC Number
- 200-731-7
- Nikkaji
- J9.177D
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -4,4
- Polarare Oberfläche (TPSA)
- 89,3 Ų
- H-Brücken-Donoren
- 3
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 4
- Schwere Atome
- 9
- Formalladung
- 0
- Komplexität
- 95
Experimentelle und physikochemische Eigenschaften
Solubility
Appreciable
620 mg/mL
Physical Description
Colorless solid; [Merck Index]
Solid
Collision Cross Section
127.7 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
129.79 Ų [M+H]+ [CCS Type: DT; Method: stepped-field]
127.81 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
121 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine]
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 100% (6 of 6) of all reports.
Not Classified
Aggregated GHS information provided per 6 reports by companies from 2 notifications to the ECHA C&L Inventory.
Gefahrenhinweise
Regulatory Information
Chemical: L-Ornithine
Status: Active Update: 13-04-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/23820
L-Ornithine: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Toxikologische Informationen
Health Effects
Chronically high levels of ornithine are associated with at least 9 inborn errors of metabolism including: Cystathionine Beta-Synthase Deficiency, Hyperornithinemia with gyrate atrophy, Hyperornithinemia-hyperammonemia-homocitrullinuria syndrome, Hyperornithinemia-hyperammonemia-homocitrullinuria syndrome, Hyperprolinemia Type II, Lysinuric Protein Intolerance, Ornithine Aminotransferase Deficiency, Ornithine Transcarbamylase Deficiency and Prolinemia Type II.
Toxicity Summary
L-Ornithine is metabolised to L-arginine. L-arginine stimulates the pituitary release of growth hormone. Burns or other injuries affect the state of L-arginine in tissues throughout the body. As De novo synthesis of L-arginine during these conditions is usually not sufficient for normal immune function, nor for normal protein synthesis, L-ornithine may have immunomodulatory and wound-healing activities under these conditions (by virtue of its metabolism to L-arginine).
Chemie und Industrie
Pharmakologische Informationen
Pharmacodynamics
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.
Mechanism of Action
L-Ornithine is metabolised to L-arginine. L-arginine stimulates the pituitary release of growth hormone. Burns or other injuries affect the state of L-arginine in tissues throughout the body. As De novo synthesis of L-arginine during these conditions is usually not sufficient for normal immune function, nor for normal protein synthesis, L-ornithine may have immunomodulatory and wound-healing activities under these conditions (by virtue of its metabolism to L-arginine).
Metabolism/Metabolites
Ornithine undergoes extensive metabolism in the liver to L-arginine, polyamines, and proline, and several other metabolites.
Ornithine undergoes extensive metabolism in the liver to L-arginine, polyamines, and proline, and several other metabolites.
Verwendung und Herstellung
Uses
A non-essential amino acid; Has been used in the treatment of hyperammonemia; [Merck Index]
Use (kg; approx.) in Germany (2009): >25000
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.
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