N-Acetyl-glutamine (YMDB01757)

Identification

YMDB ID

YMDB01757

Name

N-Acetyl-glutamine

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

N-Acetylglutamine, also known as aceglutamide or nacgln, 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. N-Acetylglutamine exists in all eukaryotes, ranging from yeast to plants to humans. Based on a literature review a significant number of articles have been published on N-Acetylglutamine.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Aceglutamid
Aceglutamide
Acetylglutamine
alpha-n-acetyl-l-glutamine
Glutamine, N2-acetyl-, L-
L-2-Acetamidoglutaramic acid
L-Glutamine, N2-acetyl-
L-N2-acetyl-Glutamine
N-acetyl-l-glutamine
N(sup2)-Acetyl-L-glutamine
N²-acetylglutamine
N2-Acetyl-L-glutamine
N2-acetylglutamine
N~2~-acetyl-L-glutamine
NAcGln
L-N2-Acetylglutamine
Α-N-acetyl-L-glutamine
(2S)-2-Acetamido-5-amino-5-oxopentanoic acid
(2S)-4-Carbamoyl-2-acetamidobutanoic acid
N-Acetylglutamine

CAS number

2490-97-3

Weight

Average: 188.1812
Monoisotopic: 188.079706882

InChI Key

KSMRODHGGIIXDV-UHFFFAOYSA-N

InChI

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)

IUPAC Name

(2S)-4-carbamoyl-2-acetamidobutanoic acid

Traditional IUPAC Name

N-acetyl-L-glutamine

Chemical Formula

C₇H₁₂N₂O₄

SMILES

CC(=O)NC(CCC(N)=O)C(O)=O

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
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 Framework

Aliphatic acyclic compounds

External Descriptors

N-acetyl-L-amino acid (CHEBI:21553 )
N(2)-acyl-L-glutamine (CHEBI:21553 )
N(2)-acetylglutamine (CHEBI:21553 )

Physical Properties

State

Solid

Charge

Melting point

197 °C

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

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	17.81 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Not Available

Organoleptic Properties

Not Available

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (4 TMS)	splash10-0udi-0792000000-c1b9c0a2e401b09330e3	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0pir-0940000000-273a364e0545e1c9660c	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0aor-1930000000-34e50f564c94c8d7eecf	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0aor-1930000000-3417e5b740846b106d28	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0aos-1910000000-40c3f40b74f5a900e804	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9300000000-80e55e189a017060034b	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-001i-9000000000-1b58f8cf05ca3b4d60f2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-001i-9000000000-d41b772a35f0471d4819	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-01qi-1920000000-03cc5cde7404917c4444	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-001l-9000000000-ae8475f16758af00d088	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-001r-2910000000-03b515be8545a7a4c32a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-001i-9810000000-4b20d607fd6455a3cc90	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-007d-0900000000-737775fcc86ca482b84f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fmj-1900000000-f6b8dadcb62c0bd29b4b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0feb-9500000000-6dbd187babd525f439e0	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-1900000000-5808e02fdf0b59805441	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002g-3900000000-d91260dd274a3a963a02	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-db717deb0ee2153fbc4c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001s-0900000000-85c4ed15c285d61aaf77	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-3900000000-a9b7bc3049cf72cfb344	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9000000000-1bfaeb4c12c7be0bca43	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-d1234af7f81ed8eb8936	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a6s-7900000000-d2a7387e0ea87eed3146	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9100000000-67fd7588646f70a13dbf	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

References

References:

Boer, V. M., Crutchfield, C. A., Bradley, P. H., Botstein, D., Rabinowitz, J. D. (2010). "Growth-limiting intracellular metabolites in yeast growing under diverse nutrient limitations." Mol Biol Cell 21:198-211.19889834

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	21553
HMDB ID	HMDB06029
Pubchem Compound ID	25561
Kegg ID	Not Available
ChemSpider ID	23836
FOODB ID	FDB023808
Wikipedia ID	Aceglutamide
BioCyc ID	Not Available

Structure for #<Compound:0xaeb5d930>