Ornithine (CHEM003289)

Record Information
Version1.0
Creation Date2014-08-29 06:27:54 UTC
Update Date2026-05-14 16:24:09 UTC
Accession NumberCHEM003289
Identification
Common NameOrnithine
ClassSmall Molecule
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 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; AF112968; ORNT1). Mutations in the mitochondrial ornithine transporter result in hyperammonemia, hyperornithinemia, homocitrullinuria (HHH) syndrome, a disorder of the urea cycle. The pathophysiology of thef 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). (1).
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • HMDB Contaminants - Urine
  • T3DB toxins
Contaminant Type
  • Amine
  • Animal Toxin
  • Dietary Supplement
  • Drug
  • Food Toxin
  • Metabolite
  • Micronutrient
  • Natural Compound
  • Non-Essential Amino Acid
  • Nutraceutical
  • Organic Compound
  • Supplement
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(S)-2,5-DiaminopentanoateChEBI
(S)-2,5-Diaminopentanoic acidChEBI
(S)-2,5-Diaminovaleric acidChEBI
(S)-alpha,delta-Diaminovaleric acidChEBI
(S)-OrnithineChEBI
(S)-2,5-DiaminovalerateGenerator
(S)-a,delta-DiaminovalerateGenerator
(S)-a,delta-Diaminovaleric acidGenerator
(S)-alpha,delta-DiaminovalerateGenerator
(S)-Α,δ-diaminovalerateGenerator
(S)-Α,δ-diaminovaleric acidGenerator
(S)-a,Δ-diaminovalerateHMDB
(S)-a,Δ-diaminovaleric acidHMDB
(+)-S-OrnithineHMDB
(S)-a,D-DiaminovalerateHMDB
(S)-a,D-Diaminovaleric acidHMDB
5-Amino-L-norvalineHMDB
L-(-)-OrnithineHMDB
L-OrnithineHMDB
2,5-Diaminopentanoic acidHMDB
Ornithine dihydrochloride, (L)-isomerHMDB
Ornithine hydrochloride, (D)-isomerHMDB
Ornithine, (D)-isomerHMDB
Ornithine, (L)-isomerHMDB
2,5 Diaminopentanoic acidHMDB
Ornithine monoacetate, (L)-isomerHMDB
Ornithine monohydrochloride, (D)-isomerHMDB
Ornithine monohydrochloride, (DL)-isomerHMDB
Ornithine phosphate (1:1), (L)-isomerHMDB
Ornithine sulfate (1:1), (L)-isomerHMDB
Ornithine hydrochloride, (DL)-isomerHMDB
Ornithine hydrochloride, (L)-isomerHMDB
Ornithine monohydrobromide, (L)-isomerHMDB
Ornithine, (DL)-isomerHMDB
Chemical FormulaC5H12N2O2
Average Molecular Mass132.161 g/mol
Monoisotopic Mass132.090 g/mol
CAS Registry Number70-26-8
IUPAC Name(2S)-2,5-diaminopentanoic acid
Traditional Nameornithine
SMILESNCCC[C@H](N)C(O)=O
InChI IdentifierInChI=1S/C5H12N2O2/c6-3-1-2-4(7)5(8)9/h4H,1-3,6-7H2,(H,8,9)/t4-/m0/s1
InChI KeyAHLPHDHHMVZTML-BYPYZUCNSA-N
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
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
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Extracellular
  • Membrane
  • Mitochondria
Biofluid LocationsNot Available
Tissue Locations
  • Gut
  • Liver
  • Prostate
  • Skin
Pathways
NameSMPDB LinkKEGG Link
Arginine and Proline MetabolismSMP00020 map00330
Glycine and Serine MetabolismSMP00004 map00260
Spermidine and Spermine BiosynthesisSMP00445 Not Available
Urea CycleSMP00059 Not Available
Cystathionine Beta-Synthase DeficiencySMP00177 Not Available
Hyperornithinemia with gyrate atrophy (HOGA)SMP00505 Not Available
Hyperornithinemia-hyperammonemia-homocitrullinuria [HHH-syndrome]SMP00506 Not Available
Hyperprolinemia Type IISMP00360 Not Available
Lysinuric Protein IntoleranceSMP00197 Not Available
Ornithine Aminotransferase Deficiency (OAT Deficiency)SMP00363 Not Available
Ornithine Transcarbamylase Deficiency (OTC Deficiency)SMP00205 Not Available
Prolinemia Type IISMP00208 Not Available
Applications
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point140°C
Boiling PointNot Available
SolubilityAppreciable
Predicted Properties
PropertyValueSource
Water Solubility172 g/LALOGPS
logP-3.6ALOGPS
logP-3.7ChemAxon
logS0.11ALOGPS
pKa (Strongest Acidic)2.67ChemAxon
pKa (Strongest Basic)10.29ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area89.34 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity33.21 m³·mol⁻¹ChemAxon
Polarizability13.85 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureAbsorbed from the small intestine via a sodium-dependent active transport process
Mechanism of ToxicityL-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).
MetabolismOrnithine undergoes extensive metabolism in the liver to L-arginine, polyamines, and proline, and several other metabolites.
Toxicity ValuesOral, rat LD50 = 10000 mg/kg
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesUsed 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.
Minimum Risk LevelNot Available
Health EffectsChronically 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.
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDDB00129
HMDB IDHMDB0000214
FooDB IDFDB030969
Phenol Explorer IDNot Available
KNApSAcK IDC00001384
BiGG ID37976
BioCyc IDL-ORNITHINE
METLIN ID27
PDB IDNot Available
Wikipedia LinkOrnithine
Chemspider ID6026
ChEBI ID15729
PubChem Compound ID6262
Kegg Compound IDC00077
YMDB IDYMDB00353
ECMDB IDECMDB23898
References
Synthesis Reference

Takayasu Tsuchida, Haruo Uchibori, Yoshitaka Nishimoto, “Process and microorganism for producing L-ornithine by Corynebacterium, Brevibacterium, or Athrobacter.” U.S. Patent US5188947, issued January, 1970.

MSDSLink
General References
1. Zhang, Peng; Zhang, Shurong; Liu, Chunqiao; Yang, Yuhong. Method for preparing L-ornithine by enzymatic conversion. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 8pp.
2. Mayer UM: [Hyperornithinaemia in patients with retinal dystrophy]. Ophthalmologe. 2003 Jan;100(1):55-61.
3. Peng CT, Wu KH, Lan SJ, Tsai JJ, Tsai FJ, Tsai CH: Amino acid concentrations in cerebrospinal fluid in children with acute lymphoblastic leukemia undergoing chemotherapy. Eur J Cancer. 2005 May;41(8):1158-63. Epub 2005 Apr 14.
4. Cynober LA: Plasma amino acid levels with a note on membrane transport: characteristics, regulation, and metabolic significance. Nutrition. 2002 Sep;18(9):761-6.
5. Gray RG, Green A, Hall S, McKeown C: Prenatal exclusion of the HHH syndrome. Prenat Diagn. 1995 May;15(5):474-6.
6. 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.
7. Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7.
8. 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.
9. 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.
10. Nicholson JK, O'Flynn MP, Sadler PJ, Macleod AF, Juul SM, Sonksen PH: Proton-nuclear-magnetic-resonance studies of serum, plasma and urine from fasting normal and diabetic subjects. Biochem J. 1984 Jan 15;217(2):365-75.
11. 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.
12. Engelborghs S, Marescau B, De Deyn PP: Amino acids and biogenic amines in cerebrospinal fluid of patients with Parkinson's disease. Neurochem Res. 2003 Aug;28(8):1145-50.
13. 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.
14. Hagenfeldt L, Bjerkenstedt L, Edman G, Sedvall G, Wiesel FA: Amino acids in plasma and CSF and monoamine metabolites in CSF: interrelationship in healthy subjects. J Neurochem. 1984 Mar;42(3):833-7.
15. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762.
16. 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.
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18. https://www.ncbi.nlm.nih.gov/pubmed/?term=17190852
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20. https://www.ncbi.nlm.nih.gov/pubmed/?term=19083482
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=19173225
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=22033378
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=22133808
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=22387109
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=22735334