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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2007-04-12 20:38:27 UTC
Update Date2021-10-13 04:47:55 UTC
HMDB IDHMDB0006029
Secondary Accession Numbers
  • HMDB06029
Metabolite Identification
Common NameN-Acetylglutamine
DescriptionN-Acetyl-L-glutamine (NAcGln) or N-Acetylglutamine, belongs to the class of organic compounds known as N-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. N-Acetylglutamine can also be classified as an alpha amino acid or a derivatized alpha amino acid. Technically, N-Acetylglutamine is a biologically available N-terminal capped form of the proteinogenic alpha amino acid L-glutamine. N-acetyl amino acids can be produced either via direct synthesis of specific N-acetyltransferases or via the proteolytic degradation of N-acetylated proteins by specific hydrolases. N-terminal acetylation of proteins is a widespread and highly conserved process in eukaryotes that is involved in protection and stability of proteins (PMID: 16465618 ). About 85% of all human proteins and 68% of all yeast proteins are acetylated at their N-terminus (PMID: 21750686 ). Several proteins from prokaryotes and archaea are also modified by N-terminal acetylation. The majority of eukaryotic N-terminal-acetylation reactions occur through N-acetyltransferase enzymes or NAT’s (PMID: 30054468 ). These enzymes consist of three main oligomeric complexes NatA, NatB, and NatC, which are composed of at least a unique catalytic subunit and one unique ribosomal anchor. The substrate specificities of different NAT enzymes are mainly determined by the identities of the first two N-terminal residues of the target protein. The human NatA complex co-translationally acetylates N-termini that bear a small amino acid (A, S, T, C, and occasionally V and G) (PMID: 30054468 ). NatA also exists in a monomeric state and can post-translationally acetylate acidic N-termini residues (D-, E-). NatB and NatC acetylate N-terminal methionine with further specificity determined by the identity of the second amino acid. N-acetylated amino acids, such as N-acetylglutamine can be released by an N-acylpeptide hydrolase from peptides generated by proteolytic degradation (PMID: 16465618 ). In addition to the NAT enzymes and protein-based acetylation, N-acetylation of free glutamine can also occur. In particular, N-Acetylglutamine can be biosynthesized from L-glutamine and acetyl-CoA by the enzyme glutamine N-acyltransferase (EC 2.3.1.68). Excessive amounts N-acetyl amino acids including N-acetylglutamine (as well as N-acetylglycine, N-acetylserine, N-acetylmethionine, N-acetylglutamate, N-acetylalanine, N-acetylleucine and smaller amounts of N-acetylthreonine, N-acetylisoleucine, and N-acetylvaline) can be detected in the urine with individuals with acylase I deficiency, a genetic disorder (PMID: 16465618 ). Aminoacylase I is a soluble homodimeric zinc binding enzyme that catalyzes the formation of free aliphatic amino acids from N-acetylated precursors. In humans, Aminoacylase I is encoded by the aminoacylase 1 gene (ACY1) on chromosome 3p21 that consists of 15 exons (OMIM 609924 ). Individuals with aminoacylase I deficiency will experience convulsions, hearing loss and difficulty feeding (PMID: 16465618 ). ACY1 can also catalyze the reverse reaction, the synthesis of acetylated amino acids. Many N-acetylamino acids, including N-acetylglutamine are classified as uremic toxins if present in high abundance in the serum or plasma (PMID: 26317986 ; PMID: 20613759 ). Uremic toxins are a diverse group of endogenously produced molecules that, if not properly cleared or eliminated by the kidneys, can cause kidney damage, cardiovascular disease and neurological deficits (PMID: 18287557 ). N-acetylglutamine can be used for parenteral nutrition as a source of glutamine since glutamine is too unstable whereas N-acetylglutamine is very stable. In patients treated with aminoglycosides and/or glycopeptides, an elevation of N-acetylglutamine in urine suggests renal tubular injury.
Structure
Data?1582752371
Synonyms
ValueSource
N~2~-acetyl-L-glutamineChEBI
N-Acetyl-L-glutamineHMDB
AceglutamideHMDB
AcetylglutamineHMDB
NAcGlnHMDB
L-N2-Acetyl-glutamineHMDB
L-N2-AcetylglutamineHMDB
N2-Acetyl-L-glutamineHMDB
N2-AcetylglutamineHMDB
alpha-N-Acetyl-L-glutamineHMDB
Α-N-acetyl-L-glutamineHMDB
(2S)-2-Acetamido-5-amino-5-oxopentanoic acidHMDB
(2S)-4-Carbamoyl-2-acetamidobutanoic acidHMDB
N-AcetylglutamineMeSH
Chemical FormulaC7H12N2O4
Average Molecular Weight188.1812
Monoisotopic Molecular Weight188.079706882
IUPAC Name(2S)-4-carbamoyl-2-acetamidobutanoic acid
Traditional NameN-acetyl-L-glutamine
CAS Registry Number2490-97-3
SMILES
CC(=O)N[C@@H](CCC(N)=O)C(O)=O
InChI Identifier
InChI=1S/C7H12N2O4/c1-4(10)9-5(7(12)13)2-3-6(8)11/h5H,2-3H2,1H3,(H2,8,11)(H,9,10)(H,12,13)/t5-/m0/s1
InChI KeyKSMRODHGGIIXDV-YFKPBYRVSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as glutamine and derivatives. Glutamine and derivatives are compounds containing glutamine or a derivative thereof resulting from reaction of glutamine 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 ParentGlutamine and derivatives
Alternative Parents
Substituents
  • Glutamine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-l-alpha-amino acid
  • N-acyl-l-glutamine
  • Fatty amide
  • Fatty acyl
  • Fatty acid
  • Acetamide
  • Carboxamide group
  • Primary carboxylic acid amide
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Adverse health effect

Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point197 °CNot Available
Boiling Point604.00 to 605.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility155300 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-2.635 (est)The Good Scents Company Information System
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg136.82430932474
[M-H]-Not Available136.827http://allccs.zhulab.cn/database/detail?ID=AllCCS00000063
Predicted Molecular Properties
PropertyValueSource
Water Solubility21.9 g/LALOGPS
logP-2.2ALOGPS
logP-1.9ChemAxon
logS-0.93ALOGPS
pKa (Strongest Acidic)3.76ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area109.49 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity42.55 m³·mol⁻¹ChemAxon
Polarizability17.81 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+136.16630932474
DeepCCS[M-H]-133.36430932474
DeepCCS[M-2H]-169.73930932474
DeepCCS[M+Na]+145.27730932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-AcetylglutamineCC(=O)N[C@@H](CCC(N)=O)C(O)=O2612.5Standard polar33892256
N-AcetylglutamineCC(=O)N[C@@H](CCC(N)=O)C(O)=O1750.3Standard non polar33892256
N-AcetylglutamineCC(=O)N[C@@H](CCC(N)=O)C(O)=O2003.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-Acetylglutamine,1TMS,isomer #1CC(=O)N[C@@H](CCC(N)=O)C(=O)O[Si](C)(C)C1791.6Semi standard non polar33892256
N-Acetylglutamine,1TMS,isomer #2CC(=O)N[C@@H](CCC(=O)N[Si](C)(C)C)C(=O)O1832.2Semi standard non polar33892256
N-Acetylglutamine,1TMS,isomer #3CC(=O)N([C@@H](CCC(N)=O)C(=O)O)[Si](C)(C)C1835.3Semi standard non polar33892256
N-Acetylglutamine,2TMS,isomer #1CC(=O)N[C@@H](CCC(=O)N[Si](C)(C)C)C(=O)O[Si](C)(C)C1899.8Semi standard non polar33892256
N-Acetylglutamine,2TMS,isomer #1CC(=O)N[C@@H](CCC(=O)N[Si](C)(C)C)C(=O)O[Si](C)(C)C1916.9Standard non polar33892256
N-Acetylglutamine,2TMS,isomer #1CC(=O)N[C@@H](CCC(=O)N[Si](C)(C)C)C(=O)O[Si](C)(C)C2658.1Standard polar33892256
N-Acetylglutamine,2TMS,isomer #2CC(=O)N([C@@H](CCC(N)=O)C(=O)O[Si](C)(C)C)[Si](C)(C)C1846.9Semi standard non polar33892256
N-Acetylglutamine,2TMS,isomer #2CC(=O)N([C@@H](CCC(N)=O)C(=O)O[Si](C)(C)C)[Si](C)(C)C1840.7Standard non polar33892256
N-Acetylglutamine,2TMS,isomer #2CC(=O)N([C@@H](CCC(N)=O)C(=O)O[Si](C)(C)C)[Si](C)(C)C2930.9Standard polar33892256
N-Acetylglutamine,2TMS,isomer #3CC(=O)N([C@@H](CCC(=O)N[Si](C)(C)C)C(=O)O)[Si](C)(C)C1890.5Semi standard non polar33892256
N-Acetylglutamine,2TMS,isomer #3CC(=O)N([C@@H](CCC(=O)N[Si](C)(C)C)C(=O)O)[Si](C)(C)C1968.4Standard non polar33892256
N-Acetylglutamine,2TMS,isomer #3CC(=O)N([C@@H](CCC(=O)N[Si](C)(C)C)C(=O)O)[Si](C)(C)C2585.9Standard polar33892256
N-Acetylglutamine,2TMS,isomer #4CC(=O)N[C@@H](CCC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O1999.5Semi standard non polar33892256
N-Acetylglutamine,2TMS,isomer #4CC(=O)N[C@@H](CCC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O1945.9Standard non polar33892256
N-Acetylglutamine,2TMS,isomer #4CC(=O)N[C@@H](CCC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O2944.2Standard polar33892256
N-Acetylglutamine,3TMS,isomer #1CC(=O)N([C@@H](CCC(=O)N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C1916.4Semi standard non polar33892256
N-Acetylglutamine,3TMS,isomer #1CC(=O)N([C@@H](CCC(=O)N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C1964.2Standard non polar33892256
N-Acetylglutamine,3TMS,isomer #1CC(=O)N([C@@H](CCC(=O)N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C2235.0Standard polar33892256
N-Acetylglutamine,3TMS,isomer #2CC(=O)N[C@@H](CCC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C2028.3Semi standard non polar33892256
N-Acetylglutamine,3TMS,isomer #2CC(=O)N[C@@H](CCC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C1974.7Standard non polar33892256
N-Acetylglutamine,3TMS,isomer #2CC(=O)N[C@@H](CCC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C2370.7Standard polar33892256
N-Acetylglutamine,3TMS,isomer #3CC(=O)N([C@@H](CCC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O)[Si](C)(C)C1976.2Semi standard non polar33892256
N-Acetylglutamine,3TMS,isomer #3CC(=O)N([C@@H](CCC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O)[Si](C)(C)C2024.4Standard non polar33892256
N-Acetylglutamine,3TMS,isomer #3CC(=O)N([C@@H](CCC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O)[Si](C)(C)C2378.5Standard polar33892256
N-Acetylglutamine,4TMS,isomer #1CC(=O)N([C@@H](CCC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C1992.3Semi standard non polar33892256
N-Acetylglutamine,4TMS,isomer #1CC(=O)N([C@@H](CCC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C2043.9Standard non polar33892256
N-Acetylglutamine,4TMS,isomer #1CC(=O)N([C@@H](CCC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C2094.4Standard polar33892256
N-Acetylglutamine,1TBDMS,isomer #1CC(=O)N[C@@H](CCC(N)=O)C(=O)O[Si](C)(C)C(C)(C)C2052.6Semi standard non polar33892256
N-Acetylglutamine,1TBDMS,isomer #2CC(=O)N[C@@H](CCC(=O)N[Si](C)(C)C(C)(C)C)C(=O)O2107.0Semi standard non polar33892256
N-Acetylglutamine,1TBDMS,isomer #3CC(=O)N([C@@H](CCC(N)=O)C(=O)O)[Si](C)(C)C(C)(C)C2063.8Semi standard non polar33892256
N-Acetylglutamine,2TBDMS,isomer #1CC(=O)N[C@@H](CCC(=O)N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2376.1Semi standard non polar33892256
N-Acetylglutamine,2TBDMS,isomer #1CC(=O)N[C@@H](CCC(=O)N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2285.7Standard non polar33892256
N-Acetylglutamine,2TBDMS,isomer #1CC(=O)N[C@@H](CCC(=O)N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2650.8Standard polar33892256
N-Acetylglutamine,2TBDMS,isomer #2CC(=O)N([C@@H](CCC(N)=O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2297.9Semi standard non polar33892256
N-Acetylglutamine,2TBDMS,isomer #2CC(=O)N([C@@H](CCC(N)=O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2258.3Standard non polar33892256
N-Acetylglutamine,2TBDMS,isomer #2CC(=O)N([C@@H](CCC(N)=O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2900.4Standard polar33892256
N-Acetylglutamine,2TBDMS,isomer #3CC(=O)N([C@@H](CCC(=O)N[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C2362.3Semi standard non polar33892256
N-Acetylglutamine,2TBDMS,isomer #3CC(=O)N([C@@H](CCC(=O)N[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C2312.3Standard non polar33892256
N-Acetylglutamine,2TBDMS,isomer #3CC(=O)N([C@@H](CCC(=O)N[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C2622.7Standard polar33892256
N-Acetylglutamine,2TBDMS,isomer #4CC(=O)N[C@@H](CCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O2448.5Semi standard non polar33892256
N-Acetylglutamine,2TBDMS,isomer #4CC(=O)N[C@@H](CCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O2324.2Standard non polar33892256
N-Acetylglutamine,2TBDMS,isomer #4CC(=O)N[C@@H](CCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O2787.2Standard polar33892256
N-Acetylglutamine,3TBDMS,isomer #1CC(=O)N([C@@H](CCC(=O)N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2579.1Semi standard non polar33892256
N-Acetylglutamine,3TBDMS,isomer #1CC(=O)N([C@@H](CCC(=O)N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2521.2Standard non polar33892256
N-Acetylglutamine,3TBDMS,isomer #1CC(=O)N([C@@H](CCC(=O)N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2555.0Standard polar33892256
N-Acetylglutamine,3TBDMS,isomer #2CC(=O)N[C@@H](CCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2664.9Semi standard non polar33892256
N-Acetylglutamine,3TBDMS,isomer #2CC(=O)N[C@@H](CCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2556.9Standard non polar33892256
N-Acetylglutamine,3TBDMS,isomer #2CC(=O)N[C@@H](CCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2593.6Standard polar33892256
N-Acetylglutamine,3TBDMS,isomer #3CC(=O)N([C@@H](CCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C2651.3Semi standard non polar33892256
N-Acetylglutamine,3TBDMS,isomer #3CC(=O)N([C@@H](CCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C2588.8Standard non polar33892256
N-Acetylglutamine,3TBDMS,isomer #3CC(=O)N([C@@H](CCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C2615.5Standard polar33892256
N-Acetylglutamine,4TBDMS,isomer #1CC(=O)N([C@@H](CCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2862.1Semi standard non polar33892256
N-Acetylglutamine,4TBDMS,isomer #1CC(=O)N([C@@H](CCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2789.6Standard non polar33892256
N-Acetylglutamine,4TBDMS,isomer #1CC(=O)N([C@@H](CCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2538.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - N-Acetylglutamine GC-MS (4 TMS)splash10-0udi-0792000000-c1b9c0a2e401b09330e32014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - N-Acetylglutamine GC-MS (3 TMS)splash10-0pir-0940000000-273a364e0545e1c9660c2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - N-Acetylglutamine GC-MS (2 TMS)splash10-0aor-1930000000-34e50f564c94c8d7eecf2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - N-Acetylglutamine EI-B (Non-derivatized)splash10-0aor-1930000000-3417e5b740846b106d282017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - N-Acetylglutamine GC-EI-TOF (Non-derivatized)splash10-0aos-1910000000-40c3f40b74f5a900e8042017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetylglutamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9300000000-80e55e189a017060034b2017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetylglutamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylglutamine 30V, Positive-QTOFsplash10-001i-9000000000-1b58f8cf05ca3b4d60f22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylglutamine 10V, Positive-QTOFsplash10-001i-9000000000-d41b772a35f0471d48192021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylglutamine 0V, Positive-QTOFsplash10-01qi-1920000000-03cc5cde7404917c44442021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylglutamine 30V, Positive-QTOFsplash10-001l-9000000000-ae8475f16758af00d0882021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylglutamine 0V, Positive-QTOFsplash10-001r-2910000000-03b515be8545a7a4c32a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylglutamine 10V, Positive-QTOFsplash10-001i-9810000000-4b20d607fd6455a3cc902021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylglutamine 10V, Positive-QTOFsplash10-007d-0900000000-737775fcc86ca482b84f2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylglutamine 20V, Positive-QTOFsplash10-0fmj-1900000000-f6b8dadcb62c0bd29b4b2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylglutamine 40V, Positive-QTOFsplash10-0feb-9500000000-6dbd187babd525f439e02017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylglutamine 10V, Negative-QTOFsplash10-000i-1900000000-5808e02fdf0b598054412017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylglutamine 20V, Negative-QTOFsplash10-002g-3900000000-d91260dd274a3a963a022017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylglutamine 40V, Negative-QTOFsplash10-0006-9100000000-db717deb0ee2153fbc4c2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylglutamine 10V, Positive-QTOFsplash10-001s-0900000000-85c4ed15c285d61aaf772021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylglutamine 20V, Positive-QTOFsplash10-001i-3900000000-a9b7bc3049cf72cfb3442021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylglutamine 40V, Positive-QTOFsplash10-001i-9000000000-1bfaeb4c12c7be0bca432021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylglutamine 10V, Negative-QTOFsplash10-004i-0900000000-d1234af7f81ed8eb89362021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylglutamine 20V, Negative-QTOFsplash10-0a6s-7900000000-d2a7387e0ea87eed31462021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylglutamine 40V, Negative-QTOFsplash10-052f-9100000000-67fd7588646f70a13dbf2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified18.557 +/- 7.493 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)FemaleEpithelial ovarian cancer details
UrineDetected and Quantified36.587 +/- 55.035 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAutosomal dominant polycystic kidney disease (ADPKD) details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal adenoma
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. 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 ]
Autosomal dominant polycystic kidney disease
  1. Gronwald W, Klein MS, Zeltner R, Schulze BD, Reinhold SW, Deutschmann M, Immervoll AK, Boger CA, Banas B, Eckardt KU, Oefner PJ: Detection of autosomal dominant polycystic kidney disease by NMR spectroscopic fingerprinting of urine. Kidney Int. 2011 Jun;79(11):1244-53. doi: 10.1038/ki.2011.30. Epub 2011 Mar 9. [PubMed:21389975 ]
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
  • 114500 (Colorectal cancer)
  • 601313 (Autosomal dominant polycystic kidney disease)
  • 610247 (Eosinophilic esophagitis)
DrugBank IDDB04167
Phenol Explorer Compound IDNot Available
FooDB IDFDB023808
KNApSAcK IDNot Available
Chemspider ID158492
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAceglutamide
METLIN IDNot Available
PubChem Compound182230
PDB IDNot Available
ChEBI ID21553
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1597951
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Van Coster RN, Gerlo EA, Giardina TG, Engelke UF, Smet JE, De Praeter CM, Meersschaut VA, De Meirleir LJ, Seneca SH, Devreese B, Leroy JG, Herga S, Perrier JP, Wevers RA, Lissens W: Aminoacylase I deficiency: a novel inborn error of metabolism. Biochem Biophys Res Commun. 2005 Dec 23;338(3):1322-6. Epub 2005 Nov 2. [PubMed:16274666 ]
  2. Sass JO, Mohr V, Olbrich H, Engelke U, Horvath J, Fliegauf M, Loges NT, Schweitzer-Krantz S, Moebus R, Weiler P, Kispert A, Superti-Furga A, Wevers RA, Omran H: Mutations in ACY1, the gene encoding aminoacylase 1, cause a novel inborn error of metabolism. Am J Hum Genet. 2006 Mar;78(3):401-9. Epub 2006 Jan 18. [PubMed:16465618 ]
  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. Magnusson I, Kihlberg R, Alvestrand A, Wernerman J, Ekman L, Wahren J: Utilization of intravenously administered N-acetyl-L-glutamine in humans. Metabolism. 1989 Aug;38(8 Suppl 1):82-8. [PubMed:2569664 ]
  5. Bergana MM, Holton JD, Reyzer IL, Snowden MK, Baxter JH, Pound VL: NMR and MS analysis of decomposition compounds produced from N-acetyl-L-glutamine at low pH. J Agric Food Chem. 2000 Dec;48(12):6003-10. [PubMed:11312773 ]
  6. Racine SX, Le Toumelin P, Adnet F, Cohen Y, Cupa M, Hantz E, Le Moyec L: N-acetyl functions and acetate detected by nuclear magnetic resonance spectroscopy of urine to detect renal dysfunction following aminoglycoside and/or glycopeptide antibiotic therapy. Nephron Physiol. 2004;97(4):p53-7. [PubMed:15331932 ]
  7. 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 ]
  8. Tanaka H, Sirich TL, Plummer NS, Weaver DS, Meyer TW: An Enlarged Profile of Uremic Solutes. PLoS One. 2015 Aug 28;10(8):e0135657. doi: 10.1371/journal.pone.0135657. eCollection 2015. [PubMed:26317986 ]
  9. Van Damme P, Hole K, Pimenta-Marques A, Helsens K, Vandekerckhove J, Martinho RG, Gevaert K, Arnesen T: NatF contributes to an evolutionary shift in protein N-terminal acetylation and is important for normal chromosome segregation. PLoS Genet. 2011 Jul;7(7):e1002169. doi: 10.1371/journal.pgen.1002169. Epub 2011 Jul 7. [PubMed:21750686 ]
  10. Ree R, Varland S, Arnesen T: Spotlight on protein N-terminal acetylation. Exp Mol Med. 2018 Jul 27;50(7):1-13. doi: 10.1038/s12276-018-0116-z. [PubMed:30054468 ]
  11. Toyohara T, Akiyama Y, Suzuki T, Takeuchi Y, Mishima E, Tanemoto M, Momose A, Toki N, Sato H, Nakayama M, Hozawa A, Tsuji I, Ito S, Soga T, Abe T: Metabolomic profiling of uremic solutes in CKD patients. Hypertens Res. 2010 Sep;33(9):944-52. doi: 10.1038/hr.2010.113. Epub 2010 Jul 8. [PubMed:20613759 ]
  12. Vanholder R, Baurmeister U, Brunet P, Cohen G, Glorieux G, Jankowski J: A bench to bedside view of uremic toxins. J Am Soc Nephrol. 2008 May;19(5):863-70. doi: 10.1681/ASN.2007121377. Epub 2008 Feb 20. [PubMed:18287557 ]

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