MiMeDB: Showing metabocard for N-Acetyl-glutamine (MMDBc0033691)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:59:10 UTC

Update Date

2024-04-30 20:15:14 UTC

Metabolite ID

MMDBc0033691

Metabolite Identification

Common Name

N-Acetyl-glutamine

Description

N-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‚Äôs (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

MOL SDF PDB SMILES InChI

HEADER    PROTEIN                                 20-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAY-19         0                                  
HETATM    1  O   UNK     0      29.394  -7.762   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      30.728  -5.452   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      32.061 -12.382   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      34.729  -9.302   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      33.395  -6.992   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      29.394 -12.382   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      32.061  -7.762   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      32.061  -9.302   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      30.728 -10.072   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      30.728  -6.992   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      30.728 -11.612   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      34.729  -7.762   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      36.063  -6.992   0.000  0.00  0.00           C+0
CONECT    1   10                                                            
CONECT    2   10                                                            
CONECT    3   11                                                            
CONECT    4   12                                                            
CONECT    5    7   12                                                       
CONECT    6   11                                                            
CONECT    7    5    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8   11                                                       
CONECT   10    1    2    7                                                  
CONECT   11    3    6    9                                                  
CONECT   12    4    5   13                                                  
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

Synonyms

Value	Source
Aceglutamide	ChEBI
Acetylglutamine	ChEBI
GlcNAc	ChEBI
Aceglutamid	HMDB
alpha-N-Acetyl-L-glutamine	HMDB
L-2-Acetamidoglutaramic acid	HMDB
L-N2-Acetyl-glutamine	HMDB
N-Acetyl-L-glutamine	HMDB
N2-Acetyl-L-glutamine	HMDB
N2-Acetylglutamine	HMDB
Aceglutamide, aluminum (3:1) salt	MeSH, HMDB
N-Acetylglutamine	ChEBI

Molecular Formula

C₇H₁₂N₂O₄

Average Mass

188.1812

Monoisotopic Mass

188.079706882

IUPAC Name

4-carbamoyl-2-acetamidobutanoic acid

Traditional Name

N-acetyl-L-glutamine

CAS Registry Number

2490-97-3

SMILES

CC(=O)NC(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)

InChI Key

KSMRODHGGIIXDV-UHFFFAOYSA-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Glutamine and derivatives

Alternative Parents

Substituents

Glutamine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
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 Framework

Aliphatic acyclic compounds

External Descriptors

N-acetyl-amino acid (CHEBI:73685 )
N(2)-acylglutamine (CHEBI:73685 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	21.9 g/L	ALOGPS
logP	-2.2	ALOGPS
logP	-1.9	ChemAxon
logS	-0.93	ALOGPS
pKa (Strongest Acidic)	3.76	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	109.49 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	42.55 m³·mol⁻¹	ChemAxon
Polarizability	17.66 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9300000000-80e55e189a017060034b	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00dl-9110000000-c1484214f430e9c081e6	2017-10-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-007d-0900000000-737775fcc86ca482b84f	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fmj-1900000000-f6b8dadcb62c0bd29b4b	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0feb-9500000000-6dbd187babd525f439e0	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-1900000000-5808e02fdf0b59805441	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002g-3900000000-d91260dd274a3a963a02	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-db717deb0ee2153fbc4c	2016-08-03	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)		2016-09-19	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental)		2016-09-19	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Placenta
Urine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Eosinophilic esophagitis		Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Urine	Detected and Quantified	36.587	55.035	umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	18.557	7.493	umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Placenta	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023808

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Aceglutamide

METLIN ID

Not Available

PubChem Compound

25561

PDB ID

Not Available

ChEBI ID

73685

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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. doi: 10.1016/0026-0495(89)90148-0. [PubMed:2569664 ]
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. doi: 10.1016/0378-4347(94)80064-2. [PubMed:7952062 ]
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. doi: 10.1021/jf000897j. [PubMed:11312773 ]
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. doi: 10.1159/000079179. [PubMed:15331932 ]
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. doi: 10.1016/j.bbrc.2005.10.126. Epub 2005 Nov 2. [PubMed:16274666 ]
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. doi: 10.1086/500563. Epub 2006 Jan 18. [PubMed:16465618 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]

Showing metabocard for N-Acetyl-glutamine (MMDBc0033691)

MOL for #<Metabolite:0x00007fa4e92641d0>

3D MOL for #<Metabolite:0x00007fa4e92641d0>

3D SDF for #<Metabolite:0x00007fa4e92641d0>

3D-SDF for #<Metabolite:0x00007fa4e92641d0>

PDB for #<Metabolite:0x00007fa4e92641d0>

3D PDB for #<Metabolite:0x00007fa4e92641d0>

SMILES for #<Metabolite:0x00007fa4e92641d0>

INCHI for #<Metabolite:0x00007fa4e92641d0>

Structure for #<Metabolite:0x00007fa4e92641d0>

3D Structure for #<Metabolite:0x00007fa4e92641d0>