Record Information
Version1.0
Creation date2015-10-09 22:27:17 UTC
Update date2017-01-19 02:36:09 UTC
FoodComEx IDPC000009
FoodDB RecordFDB003654
Chemical Information
NameOrnithine
DescriptionA 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.; AF112968; 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. Ornithine is recycled and in a manner is a catalyst. First, ammonia is converted into carbamoyl phosphate (phosphate-CONH2), which creates one half of urea. Ornithine is converted into a urea derivative at the ? (terminal) nitrogen by carbamoyl phosphate. Another nitrogen is added from aspartate, producing the denitrogenated fumarate, and the resulting arginine (a guanidinium compound) is hydrolysed back to ornithine, producing urea. The nitrogens of urea come from the ammonia and aspartate, and the nitrogen in ornithine remains intact.; 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); 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; Ornithine is an amino acid which plays a role in the urea cycle. Ornithine is found in many foods, some of which are soft-necked garlic, orange bell pepper, sunburst squash (pattypan squash), and cucumber.
CAS Number3184-13-2
Structure
Thumb
Synonyms
SynonymSource
(+)-s-ornithinebiospider
(2S)-2,5-diaminopentanoic acidbiospider
(S)-2,5-Diaminopentanoatebiospider
(S)-2,5-Diaminopentanoic acidbiospider
(S)-2,5-DiaminovalerateGenerator
(S)-2,5-diaminovaleric acidbiospider
(s)-a,d-diaminovaleratebiospider
(s)-a,d-diaminovaleric acidbiospider
(S)-a,delta-DiaminovalerateGenerator
(S)-a,delta-Diaminovaleric acidGenerator
(S)-a,δ-diaminovalerateGenerator
(S)-a,δ-diaminovaleric acidGenerator
(S)-alpha,delta-DiaminovalerateGenerator
(s)-alpha,delta-diaminovaleric acidbiospider
(s)-ornithinebiospider
(S)-α,δ-diaminovalerateGenerator
(S)-α,δ-diaminovaleric acidGenerator
2,5-diaminopentanoatebiospider
2,5-diaminopentanoic acidbiospider
2,5-diaminovaleric acidbiospider
5-amino-L-Norvalinebiospider
Alpha, delta-diaminovaleric acidbiospider
L-(-)-ornithinebiospider
L-Norvaline, 5-amino-biospider
L-OrnithineChEBI
L-Ornithine (9CI)biospider
Ornithine, L- (8CI)biospider
Pentanoic acid, 2,5-diamino-, (S)-biospider
Chemical FormulaC5H12N2O2
IUPAC name2,5-diaminopentanoic acid
InChI IdentifierInChI=1S/C5H12N2O2/c6-3-1-2-4(7)5(8)9/h4H,1-3,6-7H2,(H,8,9)
InChI KeyAHLPHDHHMVZTML-UHFFFAOYSA-N
Isomeric SMILESNCCCC(N)C(O)=O
Average Molecular Weight132.161
Monoisotopic Molecular Weight132.089877638
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Fatty acid
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Organopnictogen compound
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logP-4.22SANGSTER (1994)
Experimental Water SolubilityNot Available
Melting Point140 oC
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 3 g
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
AKSci E723
Glentham GM2431
MetaSci HMDB0000214
Sigma-Aldrich HMDB0000214
Toronto Research Chemicals O695550