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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-03-02 16:05:15 UTC
HMDB IDHMDB0001138
Secondary Accession Numbers
  • HMDB01138
Metabolite Identification
Common NameN-Acetyl-L-glutamic acid
DescriptionN-Acetyl-L-glutamic acid, also known as acetylglutamate or ac-glu-OH, belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. N-Acetyl-L-glutamic acid is a drug. N-Acetyl-L-glutamic acid (abbreviated NAcGlu) is an acetylated amino acid. N-Acetyl-L-glutamic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). N-Acetyl-L-glutamic acid exists in all living species, ranging from bacteria to humans. N-Acetyl-L-glutamic acid activates carbamoyl phosphate synthetase in the urea cycle. This is a severe neonatal disorder with fatal consequences if not detected immediately at birth. The reverse reaction, hydrolysis of the acetyl group, is catalyzed by a specific hydrolase. A deficiency in N-acetyl glutamate synthase or a genetic mutation in the gene coding for the enzyme will lead to urea cycle failure in which ammonia is not converted to urea, but rather accumulated in the blood leading to the condition called Type I hyperammonemia.
Structure
Data?1582752179
Synonyms
ValueSource
(S)-2-(Acetylamino)pentanedioic acidChEBI
Ac-glu-OHChEBI
Acetyl-L-glutamic acidChEBI
Acetylglutamic acidChEBI
L-N-Acetylglutamic acidChEBI
N-Ac-glu-OHChEBI
N-ACETYL-L-glutamATEChEBI
N-Acetylglutamic acidChEBI
(S)-2-(Acetylamino)pentanedioateGenerator
Acetyl-L-glutamateGenerator
AcetylglutamateGenerator
L-N-AcetylglutamateGenerator
N-AcetylglutamateGenerator
N-Acetylglutamic acid semialdehydeHMDB
N-Acetylglutamate, potassium salt, (L)-isomerHMDB
N-Acetylglutamate, (D)-isomerHMDB
N-Acetylglutamate, calcium salt (1:1), (L)-isomerHMDB
N-Acetylglutamate, dipotassium salt, (L)-isomerHMDB
N-Acetylglutamate, disodium salt, (L)-isomerHMDB
N-Acetylglutamate, calcium salt, (L)-isomerHMDB
N-Acetylglutamate, magnesium salt, (L)-isomerHMDB
Sodium N-acetylglutamateHMDB
N-Acetylglutamate, (DL)-isomerHMDB
N-Acetylglutamate, monosodium salt, (L)-isomerHMDB
N-Acetyl-L-glutaminic acidHMDB
alpha-(N-Acetyl)-L-glutamic acidHMDB
Α-(N-acetyl)-L-glutamic acidHMDB
NAcGluHMDB
N-Acetyl-L-glutamic acidGenerator, KEGG
Chemical FormulaC7H11NO5
Average Molecular Weight189.1659
Monoisotopic Molecular Weight189.063722467
IUPAC Name(2S)-2-acetamidopentanedioic acid
Traditional NameN-acetyl-L-glutamate
CAS Registry Number1188-37-0
SMILES
CC(=O)N[C@@H](CCC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C7H11NO5/c1-4(9)8-5(7(12)13)2-3-6(10)11/h5H,2-3H2,1H3,(H,8,9)(H,10,11)(H,12,13)/t5-/m0/s1
InChI KeyRFMMMVDNIPUKGG-YFKPBYRVSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentGlutamic acid and derivatives
Alternative Parents
Substituents
  • Glutamic acid or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Dicarboxylic acid or derivatives
  • Fatty acid
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point199 - 201 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility52 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility18.6 g/LALOGPS
logP-0.67ALOGPS
logP-1.1ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)3.43ChemAxon
pKa (Strongest Basic)-1.8ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area103.7 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity40.73 m³·mol⁻¹ChemAxon
Polarizability17.44 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 (3 TMS)splash10-0a4i-1940000000-78ee4843d1eab79c7ca3Spectrum
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0api-3930000000-e499004b087e5d741b02Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4j-0920000000-2d39b0eff0ff23756843Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0aor-1920000000-a2fe62d19e50f9db103fSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4j-0920000000-546571923f012476b58bSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0ap0-1910000000-d18f7c4035b189c1f4b6Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4r-1900000000-fc8347700abd012bf349Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9500000000-cdb488a97c5bf1952810Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0900000000-1f9f80a37aa4e37ee878Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0fb9-0900000000-5423b76f7eb4b2a17facSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-2900000000-38410c884a2999611065Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0zfr-9700000000-85acd9611312dd7df0dbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0pb9-9100000000-0d780e23d772cf133da2Spectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0ufr-1900000000-7a57de84cf9c6671cfc2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-0900000000-7b58c7204405ece93fcaSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-1900000000-515b33cc5674fc8985c8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9300000000-b379a6e4d794e810c478Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9000000000-2ce098bb9e1b35433878Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9000000000-8e7d8abde262b7d5cb45Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-001i-1900000000-a3bdc3627857c5f47f4bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-0900000000-88345aaf9776c7fb8676Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udl-2900000000-5fca3bd987ebf6b42946Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udj-9500000000-be58124b136b37456414Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-a56ffb8d475d132443a8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004v-2900000000-c32612499c0a2ceb8298Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9300000000-75dbbc130d00cfec5880Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Mitochondria
Biospecimen Locations
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Liver
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not AvailableNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected and Quantified0.0448 +/- 0.0564 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.0695 +/- 0.137 uMAdult (>18 years old)Male
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.0700 +/- 0.0525 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.0723 +/- 0.0367 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
UrineDetected and Quantified0-42 umol/mmol creatinineNewborn (0-30 days old)Both
Normal
details
UrineDetected and Quantified6.515 +/- 4.434 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified1 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Cryptosporidium infection
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
UrineDetected and Quantified26.305 +/- 30.916 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Bladder cancer
details
UrineDetected and Quantified0.5 (0.0-1.0) umol/mmol creatinineAdult (>18 years old)Both
Prostate Cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Prostate cancer
  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 ]
Eosinophilic esophagitis
  1. (). Mordechai, Hien, and David S. Wishart. .
Associated OMIM IDs
DrugBank IDDB04075
Phenol Explorer Compound IDNot Available
FooDB IDFDB022447
KNApSAcK IDNot Available
Chemspider ID64077
KEGG Compound IDC00624
BioCyc IDACETYL-GLU
BiGG IDNot Available
Wikipedia LinkN-Acetylglutamic_acid
METLIN IDNot Available
PubChem Compound70914
PDB IDNot Available
ChEBI ID17533
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis Referencehang, Xiaolin; Yang, Qiyong; Sun, Yuesheng. Preparation of N-acetyl-L-glutamic acid. Huaxue Shijie (2002), 43(7), 363-365.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Zhang W, Holzknecht RA, Butkowski RJ, Tuchman M: Immunochemical analysis of carbamyl phosphate synthetase I and ornithine transcarbamylase deficient livers: elevated N-acetylglutamate level in a liver lacking carbamyl phosphate synthetase protein. Clin Invest Med. 1990 Aug;13(4):183-8. [PubMed:2208834 ]
  2. Tavazzi B, Lazzarino G, Leone P, Amorini AM, Bellia F, Janson CG, Di Pietro V, Ceccarelli L, Donzelli S, Francis JS, Giardina B: Simultaneous high performance liquid chromatographic separation of purines, pyrimidines, N-acetylated amino acids, and dicarboxylic acids for the chemical diagnosis of inborn errors of metabolism. Clin Biochem. 2005 Nov;38(11):997-1008. Epub 2005 Sep 1. [PubMed:16139832 ]
  3. Sugahara K, Zhang J, Kodama H: Liquid chromatographic-mass spectrometric analysis of N-acetylamino acids in human urine. J Chromatogr B Biomed Appl. 1994 Jul 1;657(1):15-21. [PubMed:7952062 ]
  4. Tuchman M, Holzknecht RA: N-acetylglutamate content in liver and gut of normal and fasted mice, normal human livers, and livers of individuals with carbamyl phosphate synthetase or ornithine transcarbamylase deficiency. Pediatr Res. 1990 Apr;27(4 Pt 1):408-12. [PubMed:2342831 ]
  5. Vockley J, Vockley CM, Lin SP, Tuchman M, Wu TC, Lin CY, Seashore MR: Normal N-acetylglutamate concentration measured in liver from a new patient with N-acetylglutamate synthetase deficiency: physiologic and biochemical implications. Biochem Med Metab Biol. 1992 Feb;47(1):38-46. [PubMed:1562355 ]
  6. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Enzymes

General function:
Involved in catalytic activity
Specific function:
Involved in the urea cycle of ureotelic animals where the enzyme plays an important role in removing excess ammonia from the cell.
Gene Name:
CPS1
Uniprot ID:
P31327
Molecular weight:
165649.075
General function:
Involved in N-acetyltransferase activity
Specific function:
Plays a role in the regulation of ureagenesis by producing variable amounts of N-acetylglutamate (NAG), thus modulating carbamoylphosphate synthase I (CPSI) activity.
Gene Name:
NAGS
Uniprot ID:
Q8N159
Molecular weight:
58155.835
Reactions
Acetyl-CoA + L-Glutamic acid → Coenzyme A + N-Acetyl-L-glutamic aciddetails