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targets (14)
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Identification
Name L-Ornithine
Accession Number DB00129 (NUTR00043)
Type small molecule
Groups approved, nutraceutical
Description

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 a precursor of citrulline and arginine.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
(S)-2,5-Diaminopentanoate
(S)-2,5-Diaminopentanoic acid
(S)-2,5-diaminovaleric acid
(S)-ornithine
Salts Not Available
Brand names
Name Company
OKG Nature's Bounty
Brand mixtures Not Available
Categories
  • Dietary supplement
  • Micronutrient
  • Non-Essential Amino Acids
CAS number 70-26-8
Weight Average: 132.161
Monoisotopic: 132.089877638
Chemical Formula C5H12N2O2
InChI Key InChIKey=AHLPHDHHMVZTML-BYPYZUCNSA-N
InChI
InChI=1S/C5H12N2O2/c6-3-1-2-4(7)5(8)9/h4H,1-3,6-7H2,(H,8,9)/t4-/m0/s1
Plain Text
IUPAC Name
(2S)-2,5-diaminopentanoic acid
SMILES
NCCC[C@H](N)C(O)=O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Amino Acids
  • Carboxylic Acids and Derivatives
Substructures
  • Amino Acids
  • Hydroxy Compounds
  • Acetates
  • Aliphatic and Aryl Amines
  • Carboxylic Acids and Derivatives
Pharmacology
Indication 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.
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).
Absorption Absorbed from the small intestine via a sodium-dependent active transport process
Volume of distribution Not Available
Protein binding Not Available
Metabolism
Ornithine undergoes extensive metabolism in the liver to L-arginine, polyamines, and proline, and several other metabolites.

Important The metabolism module of DrugBank is currently in beta. Questions or suggestions? Please contact us.

Substrate Enzymes Product
L-Ornithine
    		Proline Details
    L-Ornithine
      		L-Arginine Details
      Route of elimination Not Available
      Half life Not Available
      Clearance Not Available
      Toxicity Oral, rat LD50 = 10000 mg/kg
      Affected organisms
      • Humans and other mammals
      Pathways Not Available
      Pharmacoeconomics
      Manufacturers Not Available
      Packagers Not Available
      Dosage forms
      Form Route Strength
      Capsule Oral 1000 mg
      Capsule Oral 500 mg
      Capsule Oral 650 mg
      Capsule Oral 750 mg
      Powder Oral
      Prices Not Available
      Patents Not Available
      Properties
      State solid
      Experimental Properties
      Property Value Source
      melting point 140 °C PhysProp
      water solubility Appreciable Not Available
      logP -4.22 SANGSTER (1994)
      pKa 1.94 (at 25 °C) KORTUM,G ET AL (1961)
      Predicted Properties
      Property Value Source
      water solubility 1.72e+02 g/l ALOGPS
      logP -3.6 ALOGPS
      logP -3.7 ChemAxon
      logS 0.11 ALOGPS
      pKa (strongest acidic) 2.67 ChemAxon
      pKa (strongest basic) 10.29 ChemAxon
      physiological charge 1 ChemAxon
      hydrogen acceptor count 4 ChemAxon
      hydrogen donor count 3 ChemAxon
      polar surface area 89.34 ChemAxon
      rotatable bond count 4 ChemAxon
      refractivity 33.21 ChemAxon
      polarizability 13.77 ChemAxon
      References
      Synthesis Reference Not Available
      General Reference Not Available
      External Links
      Resource Link
      KEGG Compound C01602 Link_out
      PubChem Compound 6262 Link_out
      PubChem Substance 46505239 Link_out
      ChemSpider 6026 Link_out
      ChEBI 15729 Link_out
      ChEMBL 15729 Link_out
      PharmGKB PA164783814 Link_out
      IUPHAR 725 Link_out
      Guide to Pharmacology 725 Link_out
      HET ORN Link_out
      PDRhealth http://www.pdrhealth.com/drug_info/nmdrugprofiles/nutsupdrugs/lor_0190.shtml Link_out
      Wikipedia http://en.wikipedia.org/wiki/Ornithine Link_out
      ATC Codes
      • A05BA06
      • D11AX16
      • P01CX03
      AHFS Codes Not Available
      PDB Entries
      FDA label Not Available
      MSDS show (72.9 KB)
      Interactions
      Drug Interactions Not Available
      Food Interactions Not Available
      Targets

      1. Ornithine aminotransferase, mitochondrial

      Pharmacological action: unknown
      Organism class: human
      UniProt ID: P04181 Link_out
      Gene: OAT Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      SNPs: SNPJam Report Link_out

      References:
      1. Levillain O, Balvay S, Peyrol S: Localization and differential expression of arginase II in the kidney of male and female mice. Pflugers Arch. 2005 Feb;449(5):491-503. Epub 2004 Dec 23. Pubmed
      2. Inubushi T, Takasawa T, Tuboi Y, Watanabe N, Aki K, Katunuma N: Changes of glucose metabolism and skin-collagen neogenesis in vitamin B6 deficiency. Biofactors. 2005;23(2):59-67. Pubmed
      3. Kaneko S, Ueda-Yamada M, Ando A, Matsumura S, Okuda-Ashitaka E, Matsumura M, Uyama M, Ito S: Cytotoxic effect of spermine on retinal pigment epithelial cells. Invest Ophthalmol Vis Sci. 2007 Jan;48(1):455-63. Pubmed

      2. Ornithine carbamoyltransferase, mitochondrial

      Pharmacological action: unknown
      Organism class: human
      UniProt ID: P00480 Link_out
      Gene: OTC Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      SNPs: SNPJam Report Link_out

      References:
      1. Barcelona-Andres B, Marina A, Rubio V: Gene structure, organization, expression, and potential regulatory mechanisms of arginine catabolism in Enterococcus faecalis. J Bacteriol. 2002 Nov;184(22):6289-300. Pubmed
      2. El Alami M, Dubois E, Oudjama Y, Tricot C, Wouters J, Stalon V, Messenguy F: Yeast epiarginase regulation, an enzyme-enzyme activity control: identification of residues of ornithine carbamoyltransferase and arginase responsible for enzyme catalytic and regulatory activities. J Biol Chem. 2003 Jun 13;278(24):21550-8. Epub 2003 Apr 4. Pubmed
      3. Templeton MD, Reinhardt LA, Collyer CA, Mitchell RE, Cleland WW: Kinetic analysis of the L-ornithine transcarbamoylase from Pseudomonas savastanoi pv. phaseolicola that is resistant to the transition state analogue®-N delta-(N’-sulfodiaminophosphinyl)-L-ornithine. Biochemistry. 2005 Mar 22;44(11):4408-15. Pubmed
      4. Morizono H, Cabrera-Luque J, Shi D, Gallegos R, Yamaguchi S, Yu X, Allewell NM, Malamy MH, Tuchman M: Acetylornithine transcarbamylase: a novel enzyme in arginine biosynthesis. J Bacteriol. 2006 Apr;188(8):2974-82. Pubmed

      3. Arginase-1

      Pharmacological action: unknown
      Organism class: human
      UniProt ID: P05089 Link_out
      Gene: ARG1 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      SNPs: SNPJam Report Link_out

      References:
      1. Gobert AP, Cheng Y, Wang JY, Boucher JL, Iyer RK, Cederbaum SD, Casero RA Jr, Newton JC, Wilson KT: Helicobacter pylori induces macrophage apoptosis by activation of arginase II. J Immunol. 2002 May 1;168(9):4692-700. Pubmed
      2. Iwata S, Tsujino T, Ikeda Y, Ishida T, Ueyama T, Gotoh T, Mori M, Yokoyama M: Decreased expression of arginase II in the kidneys of Dahl salt-sensitive rats. Hypertens Res. 2002 May;25(3):411-8. Pubmed
      3. Stickings P, Mistry SK, Boucher JL, Morris SM, Cunningham JM: Arginase expression and modulation of IL-1beta-induced nitric oxide generation in rat and human islets of Langerhans. Nitric Oxide. 2002 Dec;7(4):289-96. Pubmed
      4. Bansal V, Ochoa JB: Arginine availability, arginase, and the immune response. Curr Opin Clin Nutr Metab Care. 2003 Mar;6(2):223-8. Pubmed
      5. El Alami M, Dubois E, Oudjama Y, Tricot C, Wouters J, Stalon V, Messenguy F: Yeast epiarginase regulation, an enzyme-enzyme activity control: identification of residues of ornithine carbamoyltransferase and arginase responsible for enzyme catalytic and regulatory activities. J Biol Chem. 2003 Jun 13;278(24):21550-8. Epub 2003 Apr 4. Pubmed

      4. Ornithine decarboxylase antizyme

      Pharmacological action: unknown

      Binds to, and destabilizes, ornithine decarboxylase which is then degraded. Also inhibits cellular uptake of polyamines by inactivating the polyamine uptake transporter

      Organism class: human
      UniProt ID: P54368 Link_out
      Gene: OAZ1 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      SNPs: SNPJam Report Link_out

      References:
      1. Lopez-Contreras AJ, Lopez-Garcia C, Jimenez-Cervantes C, Cremades A, Penafiel R: Mouse ornithine decarboxylase-like gene encodes an antizyme inhibitor devoid of ornithine and arginine decarboxylating activity. J Biol Chem. 2006 Oct 13;281(41):30896-906. Epub 2006 Aug 17. Pubmed
      2. Yamaguchi Y, Takatsuka Y, Matsufuji S, Murakami Y, Kamio Y: Characterization of a counterpart to Mammalian ornithine decarboxylase antizyme in prokaryotes. J Biol Chem. 2006 Feb 17;281(7):3995-4001. Epub 2005 Dec 14. Pubmed
      3. Janne J, Alhonen L, Pietila M, Keinanen TA: Genetic approaches to the cellular functions of polyamines in mammals. Eur J Biochem. 2004 Mar;271(5):877-94. Pubmed

      5. Low-affinity cationic amino acid transporter 2

      Pharmacological action: unknown

      Low-affinity, high capacity permease involved in the transport of the cationic amino acids (arginine, lysine and ornithine)

      Organism class: human
      UniProt ID: P52569 Link_out
      Gene: SLC7A2 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      SNPs: SNPJam Report Link_out

      References:
      1. Yeramian A, Martin L, Arpa L, Bertran J, Soler C, McLeod C, Modolell M, Palacin M, Lloberas J, Celada A: Macrophages require distinct arginine catabolism and transport systems for proliferation and for activation. Eur J Immunol. 2006 Jun;36(6):1516-26. Pubmed
      2. Cerec V, Piquet-Pellorce C, Aly HA, Touzalin AM, Jegou B, Bauche F: Multiple pathways for cationic amino Acid transport in rat seminiferous tubule cells. Biol Reprod. 2007 Feb;76(2):241-9. Epub 2006 Oct 25. Pubmed
      3. Endo M, Oyadomari S, Terasaki Y, Takeya M, Suga M, Mori M, Gotoh T: Induction of arginase I and II in bleomycin-induced fibrosis of mouse lung. Am J Physiol Lung Cell Mol Physiol. 2003 Aug;285(2):L313-21. Epub 2003 Apr 4. Pubmed

      6. Mitochondrial ornithine transporter 2

      Pharmacological action: unknown

      Ornithine transport across inner mitochondrial membrane, from the cytoplasm to the matrix

      Organism class: human
      UniProt ID: Q9BXI2 Link_out
      Gene: SLC25A2 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      SNPs: SNPJam Report Link_out

      References:
      1. Camacho JA, Rioseco-Camacho N, Andrade D, Porter J, Kong J: Cloning and characterization of human ORNT2: a second mitochondrial ornithine transporter that can rescue a defective ORNT1 in patients with the hyperornithinemia-hyperammonemia-homocitrullinuria syndrome, a urea cycle disorder. Mol Genet Metab. 2003 Aug;79(4):257-71. Pubmed
      2. Begum L, Jalil MA, Kobayashi K, Iijima M, Li MX, Yasuda T, Horiuchi M, del Arco A, Satrustegui J, Saheki T: Expression of three mitochondrial solute carriers, citrin, aralar1 and ornithine transporter, in relation to urea cycle in mice. Biochim Biophys Acta. 2002 Apr 12;1574(3):283-92. Pubmed
      3. Camacho JA, Mardach R, Rioseco-Camacho N, Ruiz-Pesini E, Derbeneva O, Andrade D, Zaldivar F, Qu Y, Cederbaum SD: Clinical and functional characterization of a human ORNT1 mutation (T32R) in the hyperornithinemia-hyperammonemia-homocitrullinuria (HHH) syndrome. Pediatr Res. 2006 Oct;60(4):423-9. Epub 2006 Aug 28. Pubmed

      7. Cationic amino acid transporter 4

      Pharmacological action: unknown

      Involved in the transport of the cationic amino acids (arginine, lysine and ornithine)

      Organism class: human
      UniProt ID: O43246 Link_out
      Gene: SLC7A4 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      SNPs: SNPJam Report Link_out

      References:
      1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
      2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

      8. High-affinity cationic amino acid transporter 1

      Pharmacological action: unknown

      High-affinity, low capacity permease involved in the transport of the cationic amino acids (arginine, lysine and ornithine) in non-hepatic tissues. May also function as an ecotropic retroviral leukemia receptor

      Organism class: human
      UniProt ID: P30825 Link_out
      Gene: SLC7A1 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      SNPs: SNPJam Report Link_out

      References:
      1. Rotmann A, Strand D, Martine U, Closs EI: Protein kinase C activation promotes the internalization of the human cationic amino acid transporter hCAT-1. A new regulatory mechanism for hCAT-1 activity. J Biol Chem. 2004 Dec 24;279(52):54185-92. Epub 2004 Oct 15. Pubmed
      2. Cerec V, Piquet-Pellorce C, Aly HA, Touzalin AM, Jegou B, Bauche F: Multiple pathways for cationic amino Acid transport in rat seminiferous tubule cells. Biol Reprod. 2007 Feb;76(2):241-9. Epub 2006 Oct 25. Pubmed
      3. Yeramian A, Martin L, Arpa L, Bertran J, Soler C, McLeod C, Modolell M, Palacin M, Lloberas J, Celada A: Macrophages require distinct arginine catabolism and transport systems for proliferation and for activation. Eur J Immunol. 2006 Jun;36(6):1516-26. Pubmed

      9. Arginase-2, mitochondrial

      Pharmacological action: unknown

      May play a role in the regulation of extra-urea cycle arginine metabolism and also in down-regulation of nitric oxide synthesis. Extrahepatic arginase functions to regulate L-arginine bioavailability to NO synthase. Since NO synthase is found in the penile corpus cavernosum smooth muscle, the clitoral corpus cavernosum and the vagina, arginase II plays a role in both male and female sexual arousal. It is therefore a potential target for the treatment of male and female sexual arousal disorders

      Organism class: human
      UniProt ID: P78540 Link_out
      Gene: ARG2 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      SNPs: SNPJam Report Link_out

      References:
      1. Rodriguez PC, Zea AH, DeSalvo J, Culotta KS, Zabaleta J, Quiceno DG, Ochoa JB, Ochoa AC: L-arginine consumption by macrophages modulates the expression of CD3 zeta chain in T lymphocytes. J Immunol. 2003 Aug 1;171(3):1232-9. Pubmed
      2. Levillain O, Hus-Citharel A, Garvi S, Peyrol S, Reymond I, Mutin M, Morel F: Ornithine metabolism in male and female rat kidney: mitochondrial expression of ornithine aminotransferase and arginase II. Am J Physiol Renal Physiol. 2004 Apr;286(4):F727-38. Epub 2004 Feb 10. Pubmed
      3. Levillain O, Diaz JJ, Blanchard O, Dechaud H: Testosterone down-regulates ornithine aminotransferase gene and up-regulates arginase II and ornithine decarboxylase genes for polyamines synthesis in the murine kidney. Endocrinology. 2005 Feb;146(2):950-9. Epub 2004 Nov 11. Pubmed
      4. Bussiere FI, Chaturvedi R, Cheng Y, Gobert AP, Asim M, Blumberg DR, Xu H, Kim PY, Hacker A, Casero RA Jr, Wilson KT: Spermine causes loss of innate immune response to Helicobacter pylori by inhibition of inducible nitric-oxide synthase translation. J Biol Chem. 2005 Jan 28;280(4):2409-12. Epub 2004 Nov 17. Pubmed
      5. Nissim I, Luhovyy B, Horyn O, Daikhin Y, Nissim I, Yudkoff M: The role of mitochondrially bound arginase in the regulation of urea synthesis: studies with [U-15N4]arginine, isolated mitochondria, and perfused rat liver. J Biol Chem. 2005 May 6;280(18):17715-24. Epub 2005 Mar 7. Pubmed

      10. Mitochondrial ornithine transporter 1

      Pharmacological action: unknown

      Ornithine transport across inner mitochondrial membrane, from the cytoplasm to the matrix

      Organism class: human
      UniProt ID: Q9Y619 Link_out
      Gene: SLC25A15 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      SNPs: SNPJam Report Link_out

      References:
      1. Korman SH, Kanazawa N, Abu-Libdeh B, Gutman A, Tsujino S: Hyperornithinemia, hyperammonemia, and homocitrullinuria syndrome with evidence of mitochondrial dysfunction due to a novel SLC25A15 (ORNT1) gene mutation in a Palestinian family. J Neurol Sci. 2004 Mar 15;218(1-2):53-8. Pubmed
      2. Camacho JA, Mardach R, Rioseco-Camacho N, Ruiz-Pesini E, Derbeneva O, Andrade D, Zaldivar F, Qu Y, Cederbaum SD: Clinical and functional characterization of a human ORNT1 mutation (T32R) in the hyperornithinemia-hyperammonemia-homocitrullinuria (HHH) syndrome. Pediatr Res. 2006 Oct;60(4):423-9. Epub 2006 Aug 28. Pubmed

      11. Cationic amino acid transporter 3

      Pharmacological action: unknown

      Mediates the uptake of the cationic amino acids arginine, lysine and ornithine in a sodium-independent manner

      Organism class: human
      UniProt ID: Q8WY07 Link_out
      Gene: SLC7A3 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      SNPs: SNPJam Report Link_out

      References:
      1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
      2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
      3. Hosokawa H, Sawamura T, Kobayashi S, Ninomiya H, Miwa S, Masaki T: Cloning and characterization of a brain-specific cationic amino acid transporter. J Biol Chem. 1997 Mar 28;272(13):8717-22. Pubmed

      12. Ornithine decarboxylase antizyme 2

      Pharmacological action: unknown

      Binds to, and destabilizes, ornithine decarboxylase. Does not accelerate ornithine decarboxylase degeneration

      Organism class: human
      UniProt ID: O95190 Link_out
      Gene: OAZ2 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      SNPs: SNPJam Report Link_out

      References:
      1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
      2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

      13. Glycine amidinotransferase, mitochondrial

      Pharmacological action: unknown
      Organism class: human
      UniProt ID: P50440 Link_out
      Gene: GATM Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      SNPs: SNPJam Report Link_out

      References:
      1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
      2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
      3. Thomasset N, Quash GA, Dore JF: The differential contribution of arginase and transamidinase to ornithine biosynthesis in two achromic human melanoma cell lines. FEBS Lett. 1982 Nov 1;148(1):63-6. Pubmed
      4. Natesan S, Reddy SR: Compensatory changes in enzymes of arginine metabolism during renal hypertrophy in mice. Comp Biochem Physiol B Biochem Mol Biol. 2001 Dec;130(4):585-95. Pubmed
      5. Mitruka BM, Costilow RN: Arginine and ornithine catabolism by Clostridium botulinum. J Bacteriol. 1967 Jan;93(1):295-301. Pubmed

      14. Ornithine decarboxylase antizyme 3

      Pharmacological action: unknown

      Binds to, and destabilizes, ornithine decarboxylase. Does not accelerate ornithine decarboxylase degeneration. OAZ3 probably plays a key role in spermatogenesis by regulating the intracellular concentration of polyamines in haploid germ cells

      Organism class: human
      UniProt ID: Q9UMX2 Link_out
      Gene: OAZ3 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      SNPs: SNPJam Report Link_out

      References:
      1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
      2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
      Comments
      Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19