You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-12 19:18:46 UTC
Update Date2020-02-27 16:50:58 UTC
HMDB IDHMDB0003357
Secondary Accession Numbers
  • HMDB0006489
  • HMDB03357
  • HMDB06489
Metabolite Identification
Common NameN2-Acetylornithine
DescriptionN2-Acetylornithine, also known as N(alpha)-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. N-Acetylornithine is a minor component of the deproteinized blood plasma of human blood. Human blood plasma contains a variable amount of acetylornithine, averaging 1.1 +/- 0.4 umol/L (range 0.8-0.2 umol/L). Urine contains a very small amount of acetylornithine, approximately 1 nmol/mg creatinine (1 umol/day) (PMID: 508804 ).
Structure
Data?1582752272
Synonyms
ValueSource
N2-Acetyl-L-ornithineChEBI
(2S)-2-Acetamido-5-aminopentanoateHMDB
(2S)-2-Acetamido-5-aminopentanoic acidHMDB
Acetyl-ornithineHMDB
AORHMDB
N(2)-Acetyl-L-ornithineHMDB
(2S)-5-Amino-2-acetamidopentanoic acidHMDB
N(alpha)-Acetyl-L-ornithineHMDB
N(alpha)-AcetylornithineHMDB
N(α)-Acetyl-L-ornithineHMDB
N(α)-AcetylornithineHMDB
N-Acetyl-L-ornithineHMDB
N-AcetylornithineHMDB
Nalpha-Acetyl-L-ornithineHMDB
Nalpha-AcetylornithineHMDB
Nα-Acetyl-L-ornithineHMDB
Nα-AcetylornithineHMDB
N2-AcetylornithineHMDB
N-alpha-AcetylornithineHMDB
N-α-AcetylornithineHMDB
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 effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-0.896Not Available
Predicted Properties
PropertyValueSource
Water Solubility37.8 g/LALOGPS
logP-2.7ALOGPS
logP-3.6ChemAxon
logS-0.66ALOGPS
pKa (Strongest Acidic)3.82ChemAxon
pKa (Strongest Basic)9.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area92.42 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity42.65 m³·mol⁻¹ChemAxon
Polarizability17.94 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0fk9-1930000000-28d5f476677a51e2f8ecSpectrum
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-00di-2900000000-092b404eaa0526439b15Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0fk9-0930000000-6914c12040164b5148b0Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-0910000000-25d42f7fce94b1cb4b5cSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fk9-1920000000-e1b66d25c11eafd0e0a9Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-1900000000-0f0883367079e716da18Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0fk9-1930000000-28d5f476677a51e2f8ecSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-2900000000-092b404eaa0526439b15Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001l-9100000000-429f70cb44411bb90989Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fkc-9410000000-cee666cdbec55f97a0a0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0900000000-52f0d0fb8a9a849e95d6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0900000000-d83ff24b1fd0244f8e2eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-2900000000-e708e107e9183bfe0f76Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-053r-9400000000-afb6a5b65f59f01dc761Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4l-9000000000-4763dc8edae338a7f336Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-0900000000-d157410f17955c8e0256Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-0900000000-52b9626c047fdc01fe7bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014i-1900000000-c92081162e58f54cd2ecSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-9200000000-476b94e0eacd5c51da0dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-9000000000-e57c224e36a05f66f1b9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-9000000000-44d1c5e14f69e175989aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-03fr-0900000000-5fe61be67a41d8d0faccSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-01b9-4900000000-624c1afbfd5d3b3b76cbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-01b9-4900000000-624c1afbfd5d3b3b76cbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-1900000000-28d5e48c6fc3a56a4937Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06tr-4900000000-8aa79d29a3d89249bf78Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01vx-9200000000-2f866830ef23136853fcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-9b37a30ee623b4f18e80Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0c30-4900000000-019d18f26e04ab2b397aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9100000000-b133fb2ce9e1a5eef782Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.30-2.00 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified1.1 +/- 0.4 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified1.03 +/- 0.78 uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified10 +/- 10 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected and Quantified1.73 +/- 1.27 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
UrineDetected and Quantified2.4596 +/- 1.69 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected and Quantified0.12-3.46 umol/mmol creatinineNewborn (0-30 days old)BothNormal
    • López Hernández Y...
details
UrineDetected and Quantified0.42(0.14-3.3) umol/mmol creatinineNewborn (0-30 days old)FemaleNormal
    • López Hernández Y...
details
UrineDetected and Quantified0.41(0.12-3.50) umol/mmol creatinineNewborn (0-30 days old)MaleNormal
    • López Hernández Y...
details
UrineDetected and Quantified1.3 (0.5-2.8) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
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
    • Mordechai, Hien, ...
details
UrineDetected and Quantified1.4016 +/- 0.9775 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Mordechai, Hien, ...
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. (). Mordechai, Hien, and David S. Wishart. .
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB031020
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 ID
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