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Record Information
Version3.6
Creation Date2006-08-12 19:18:46 UTC
Update Date2017-08-16 04:08:18 UTC
HMDB IDHMDB0003357
Secondary Accession Numbers
  • HMDB03357
  • HMDB06489
Metabolite Identification
Common NameN-Acetylornithine
DescriptionN-Acetylornithine is a minor components of deproteinized blood plasma of human blood. Human blood plasma contains a variable amount of acetylornithine, averaging 1.1 +/- 0.4 mumol/l (range 0.8--0.2 mumol/l). Urine contains a very small amount of acetylornithine, approximately 1 nmol/mg creatinine (1 mumol/day). (PMID: 508804 ).
Structure
Thumb
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
N(delta)-AcetylornithineMeSH
N(delta)-Acetylornithine, (DL)-isomerMeSH
delta-N-AcetylornithineMeSH
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 NumberNot Available
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
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
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
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Protein synthesis, amino acid biosynthesis
ApplicationNot Available
Cellular locationsNot Available
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity42.65 m3·mol-1ChemAxon
Polarizability17.94 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0fk9-1930000000-28d5f476677a51e2f8ecView in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-00di-2900000000-092b404eaa0526439b15View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
GC-MSGC-MS Spectrum - EI-Bsplash10-0fk9-0930000000-6914c12040164b5148b0View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-00di-0910000000-25d42f7fce94b1cb4b5cView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0fk9-1920000000-e1b66d25c11eafd0e0a9View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-00di-1900000000-0f0883367079e716da18View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0900000000-52f0d0fb8a9a849e95d6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0900000000-d83ff24b1fd0244f8e2eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-2900000000-e708e107e9183bfe0f76View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-053r-9400000000-afb6a5b65f59f01dc761View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4l-9000000000-4763dc8edae338a7f336View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-0900000000-d157410f17955c8e0256View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-0900000000-52b9626c047fdc01fe7bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014i-1900000000-c92081162e58f54cd2ecView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-9200000000-476b94e0eacd5c51da0dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-9000000000-e57c224e36a05f66f1b9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-9000000000-44d1c5e14f69e175989aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03fr-0900000000-5fe61be67a41d8d0faccView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-01b9-4900000000-624c1afbfd5d3b3b76cbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-01b9-4900000000-624c1afbfd5d3b3b76cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-1900000000-28d5e48c6fc3a56a4937View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06tr-4900000000-8aa79d29a3d89249bf78View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01vx-9200000000-2f866830ef23136853fcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-9b37a30ee623b4f18e80View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0c30-4900000000-019d18f26e04ab2b397aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9100000000-b133fb2ce9e1a5eef782View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Saliva
  • Urine
Tissue Location
  • Prostate
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>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 Quantified1.3 (0.5-2.8) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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 ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023152
KNApSAcK IDNot Available
Chemspider ID388369
KEGG Compound IDC00437
BioCyc IDN-ALPHA-ACETYLORNITHINE
BiGG ID34982
Wikipedia LinkNot Available
NuGOwiki LinkHMDB0003357
METLIN IDNot Available
PubChem Compound439232
PDB IDAOR
ChEBI ID16543
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
N-Acetylornithine + Water → Acetic acid + Ornithinedetails