Record Information
Version1.0
Creation date2010-04-08 22:05:54 UTC
Update date2019-11-26 02:59:28 UTC
Primary IDFDB003654
Secondary Accession Numbers
  • FDB009998
Chemical Information
FooDB 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
2,5-Diaminopentanoic acidChEBI
2,5-Diaminovaleric acidChEBI
DL-OrnithineChEBI
OrnChEBI
2,5-DiaminopentanoateKegg
2,5-DiaminovalerateGenerator
L-Ornithine monochlorohydric acid/ornithineGenerator
(+/-)-2,5-diaminopentanoic acid monohydrochlorideHMDB
2,5-Diaminopentanoic acid hydrochlorideHMDB
D -2,5-Diaminopentanoic acidHMDB
D-OrnithineHMDB
DL -2,5-Diaminopentanoic acidHMDB
DL-Ornithine HCLHMDB
DL-Ornithine monohydrochlorideHMDB
DL-Ornithine, hydrochlorideHMDB
L -2,5-Diaminopentanoic acidHMDB
L-Ornithine hydrochlorideHMDB
L-Ornithine monohydrochlorideHMDB
L-Ornithine, monohydrochlorideHMDB
L-Ornithine-carboxy-14C hydrochlorideHMDB
MonohydrochlorideDL-ornithineHMDB
Monohydrochloridel-ornithineHMDB
Ornithine DL-form HCLHMDB
Ornithine DL-form monohydrochlorideHMDB
Ornithine hydrochlorideHMDB
Ornithine monohydrochlorideHMDB
Ornithine, hydrochloride (1:1)HMDB
Ornithine, monohydrochlorideHMDB
Poly-L-ornithine hydrochlorideHMDB
Ornithine sulfate (1:1), (L)-isomerMeSH
Ornithine hydrochloride, (D)-isomerMeSH
Ornithine monohydrochloride, (DL)-isomerMeSH
Ornithine, (L)-isomerMeSH
Ornithine hydrochloride, (L)-isomerMeSH
Ornithine monohydrobromide, (L)-isomerMeSH
Ornithine, (DL)-isomerMeSH
Ornithine monohydrochloride, (D)-isomerMeSH
2,5 Diaminopentanoic acidMeSH
Ornithine dihydrochloride, (L)-isomerMeSH
Ornithine phosphate (1:1), (L)-isomerMeSH
Ornithine hydrochloride, (DL)-isomerMeSH
Ornithine monoacetate, (L)-isomerMeSH
Ornithine, (D)-isomerMeSH
(+)-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
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
Polarizability13.93 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
Classification
Description 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
Ontology
Disposition

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting Point140 oC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logP-4.22SANGSTER (1994)
Experimental pKa1.94
Isoelectric pointNot Available
Charge+1
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSOrnithine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001u-9000000000-deb45bcb4280a1e67a8fSpectrum
Predicted GC-MSOrnithine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0019-9100000000-67a994a61d82dc152d64Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-01q9-8900000000-2e4d4d66936dd4f319b6Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-001i-0900000000-32310ed59a11fecc22eeSpectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-001i-0900000000-f961bdc91f8c937f8007Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-03xr-0900000000-aaa6fc0b534b5ae6a77fSpectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-00xr-8900000000-ff44915c48b3380e7423Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-00xr-8900000000-e4ce3191e51be8f7b59aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-015i-9800000000-110d911afecf530f72fdSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-9100000000-5fa5c7cc1ac450fca1d9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-9000000000-91631a0a6d3c31d893d5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1900000000-4d97ca74bc7987b5c724Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01q9-6900000000-a4a407f12771e9b56e13Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000000000-7a4945316591ef8dd14aSpectrum
NMRNot Available
ChemSpider ID6026
ChEMBL IDCHEMBL446143
KEGG Compound IDC00077
Pubchem Compound ID6262
Pubchem Substance IDNot Available
ChEBI ID18257
Phenol-Explorer IDNot Available
DrugBank IDDB00129
HMDB IDHMDB00214
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDORNITHINE
BIGG ID37976
KNApSAcK IDNot Available
HET IDORN
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDOrnithine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti cholesteremicDUKE
antidote50247 Any protective agent counteracting or neutralizing the action of poisons.DUKE
anti encephalopathic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
hypoammonemicDUKE
hypoarginanemicDUKE
Enzymes
NameGene NameUniProt ID
Glycine amidinotransferase, mitochondrialGATMP50440
Ornithine aminotransferase, mitochondrialOATP04181
Ornithine decarboxylaseODC1P11926
Ornithine decarboxylase antizyme 1OAZ1P54368
High affinity cationic amino acid transporter 1SLC7A1P30825
Delta-1-pyrroline-5-carboxylate synthaseALDH18A1P54886
Ornithine carbamoyltransferase, mitochondrialOTCP00480
Cationic amino acid transporter 4SLC7A4O43246
Mitochondrial ornithine transporter 1SLC25A15Q9Y619
Mitochondrial ornithine transporter 2SLC25A2Q9BXI2
Low affinity cationic amino acid transporter 2SLC7A2P52569
Ornithine decarboxylase antizyme 2OAZ2O95190
Ornithine decarboxylase antizyme 3OAZ3Q9UMX2
Antizyme inhibitor 1AZIN1O14977
Pathways
NameSMPDB LinkKEGG Link
Arginine and Proline MetabolismSMP00020 map00330
Glycine and Serine MetabolismSMP00004 map00260
Spermidine and Spermine BiosynthesisSMP00445 Not Available
Urea CycleSMP00059 map00330
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).