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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-12 19:18:46 UTC
Update Date2023-02-21 17:16:37 UTC
HMDB IDHMDB0003357
Secondary Accession Numbers
  • HMDB0006489
  • HMDB03357
  • HMDB06489
Metabolite Identification
Common NameN2-Acetylornithine
DescriptionN2-Acetylornithine belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom. N2-Acetylornithine exists in all living species, ranging from bacteria to plants to humans. N2-Acetylornithine is found, on average, in the highest concentration within a few different foods, such as wheats (Triticum), nanking cherries (Prunus tomentosa), and red raspberries (Rubus idaeus) and in a lower concentration in red bell peppers (Capsicum annuum), dills (Anethum graveolens), and carrots (Daucus carota ssp. sativus). N2-Acetylornithine has also been detected, but not quantified in, several different foods, such as arabica coffees (Coffea arabica), pears (Pyrus communis), black chokeberries (Photinia melanocarpa), macadamia nuts (Macadamia), and garland chrysanthemums (Chrysanthemum coronarium). This could make N2-acetylornithine a potential biomarker for the consumption of these foods. N2-Acetylornithine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on N2-Acetylornithine.
Structure
Thumb
Synonyms
Chemical FormulaC7H14N2O3
Average Molecular Weight174.1977
Monoisotopic Molecular Weight174.100442324
IUPAC Name(2S)-5-amino-2-acetamidopentanoic acid
Traditional NameN(2)-acetyl-L-ornithine
CAS Registry Number6205-08-9
SMILES
CC(=O)N[C@@H](CCCN)C(O)=O
InChI Identifier
InChI=1S/C7H14N2O3/c1-5(10)9-6(7(11)12)3-2-4-8/h6H,2-4,8H2,1H3,(H,9,10)(H,11,12)/t6-/m0/s1
InChI KeyJRLGPAXAGHMNOL-LURJTMIESA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated 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 ParentN-acyl-L-alpha-amino acids
Alternative Parents
Substituents
  • N-acyl-l-alpha-amino acid
  • Fatty acid
  • Acetamide
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Amino acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-0.896Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+MetCCS_train_pos136.94930932474
[M+H]+Not Available136.936http://allccs.zhulab.cn/database/detail?ID=AllCCS00000501
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Prostate
Pathways
Normal Concentrations
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleSupragingival Plaque details
UrineDetected and Quantified1.5724 +/- 1.5478 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
details
UrineDetected and Quantified1.4016 +/- 0.9775 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Analysis of 30 no...
details
Associated Disorders and Diseases
Disease References
Supragingival Plaque
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023152
KNApSAcK IDNot Available
Chemspider ID388369
KEGG Compound IDC00437
BioCyc IDN-ALPHA-ACETYLORNITHINE
BiGG ID34982
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound439232
PDB IDNot Available
ChEBI ID16543
Food Biomarker OntologyNot Available
VMH IDACORN
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:19212411 ]
  2. Armstrong MD: N-delta-acetylornithine and S-methylcysteine in blood plasma. Biochim Biophys Acta. 1979 Nov 1;587(4):638-42. [PubMed:508804 ]

Enzymes

General function:
Involved in metallopeptidase activity
Specific function:
Involved in the hydrolysis of N-acylated or N-acetylated amino acids (except L-aspartate).
Gene Name:
ACY1
Uniprot ID:
Q03154
Molecular weight:
45884.705
Reactions
N2-Acetylornithine + Water → Acetic acid + Ornithinedetails