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Record Information
Version1.0
Creation Date2016-09-30 22:26:50 UTC
Update Date2020-06-04 20:49:03 UTC
MCDB ID BMDB0000214
Secondary Accession Numbers
  • BMDB00214
Metabolite Identification
Common NameOrnithine
DescriptionOrnithine, also known as (S)-ornithine, 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. Ornithine is a drug which is 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. Ornithine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Ornithine exists in all living species, ranging from bacteria to humans. Ornithine participates in a number of enzymatic reactions, within cattle. In particular, Carbamoyl phosphate and ornithine can be converted into citrulline; which is mediated by the enzyme ornithine carbamoyltransferase, mitochondrial. In addition, Ornithine and urea can be biosynthesized from L-arginine; which is mediated by the enzyme arginase-1. In cattle, ornithine is involved in the metabolic pathway called the urea cycle pathway. Ornithine is a potentially toxic compound.
Structure
Thumb
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 Weight132.161
Monoisotopic Molecular Weight132.089877638
IUPAC Name(2S)-2,5-diaminopentanoic acid
Traditional Nameornithine
CAS Registry Number3184-13-2
SMILES
NCCC[C@H](N)C(O)=O
InChI Identifier
InChI=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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point140 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility620 mg/mLNot Available
LogP-4.22SANGSTER (1994)
Predicted Properties
PropertyValueSource
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable details
Detected but not QuantifiedNot Applicable details
Detected and Quantified2 - 15 uM details
HMDB IDHMDB0000214
DrugBank IDDB00129
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030969
KNApSAcK IDC00001384
Chemspider ID6026
KEGG Compound IDC00077
BioCyc IDORNITHINE
BiGG ID37976
Wikipedia LinkOrnithine
METLIN ID27
PubChem Compound6262
PDB IDNot Available
ChEBI ID15729
References
Synthesis ReferenceZhang, Peng; Zhang, Shurong; Liu, Chunqiao; Yang, Yuhong. Method for preparing L-ornithine by enzymatic conversion. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 8pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563. [PubMed:20338431 ]
  2. Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30. [PubMed:25087032 ]
  3. Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15. [PubMed:23497994 ]
  4. Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]