P. aeruginosa Metabolome Database: N-Acetyl-L-glutamate 5-semialdehyde (PAMDB000675)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 12:54:54 PM

Metabolite ID

PAMDB000675

Identification

Name:

N-Acetyl-L-glutamate 5-semialdehyde

Description:

N-Acetyl-L-glutamate 5-semialdehyde is an intermediate in Urea cycle and metabolism of amino groups. N-Acetyl-L-glutamate 5-semialdehyde is the

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

2-Acetamido-5-oxopentanoate
2-Acetamido-5-oxopentanoic acid
N-acetyl-L-glutamate semialdehyde
N-acetyl-L-glutamate-5-semialdehyde
N-acetylglutamate γ-semialdehyde
N-acetylglutamate semialdehyde
N-Acetyl-L-glutamate semialdehyde
N-Acetyl-L-glutamate-5-semialdehyde
N-Acetyl-L-glutamic acid 5-semialdehyde
N-Acetyl-L-glutamic acid semialdehyde
n-Acetyl-L-glutamic acid-5-semialdehyde
N-Acetyl-L-glutamic acid-5-semialdehyde
n-Acetylglutamate γ-semialdehyde
N-Acetylglutamate g-semialdehyde
N-Acetylglutamate gamma-semialdehyde
N-Acetylglutamate semialdehyde
N-Acetylglutamate γ-semialdehyde
n-Acetylglutamic acid γ-semialdehyde
N-Acetylglutamic acid g-semialdehyde
N-Acetylglutamic acid gamma-semialdehyde
N-Acetylglutamic acid semialdehyde
N-Acetylglutamic acid γ-semialdehyde
N-AcGlu-semialdehyde

Chemical Formula:

C₇H₁₁NO₄

Average Molecular Weight:

173.1665

Monoisotopic Molecular Weight:

173.068807845

InChI Key:

BCPSFKBPHHBDAI-LURJTMIESA-N

InChI:

InChI=1S/C7H11NO4/c1-5(10)8-6(7(11)12)3-2-4-9/h4,6H,2-3H2,1H3,(H,8,10)(H,11,12)/t6-/m0/s1

CAS number:

13074-21-0

IUPAC Name:

(2S)-2-acetamido-5-oxopentanoic acid

Traditional IUPAC Name:

N-acetyl-5-oxo-L-norvaline

SMILES:

CC(=O)N[C@@H](CCC=O)C(O)=O

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as n-acyl-aliphatic-alpha amino acids. These are alpha amino acids carrying a N-acylated aliphatic chain.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-aliphatic-alpha amino acids

Alternative Parents

Substituents

N-acyl-aliphatic-alpha amino acid
N-acyl-l-alpha-amino acid
Amino fatty acid
Fatty acyl
Fatty acid
Acetamide
Alpha-hydrogen aldehyde
Secondary carboxylic acid amide
Carboxamide group
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid amide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aldehyde
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

glutamic semialdehyde (CHEBI:16319 )

Physical Properties

State:

Solid

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	18.6 mg/mL	ALOGPS
logP	-0.43	ALOGPS
logP	-1.3	ChemAxon
logS	-0.97	ALOGPS
pKa (Strongest Acidic)	3.72	ChemAxon
pKa (Strongest Basic)	-1.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.47 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	39.81 m³·mol^-1	ChemAxon
Polarizability	16.46 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:

Cytoplasm

Reactions:

N-Acetylornithine + alpha-Ketoglutarate <> N-Acetyl-L-glutamate 5-semialdehyde + L-Glutamate
N-Acetyl-L-glutamate 5-semialdehyde + Water > Acetic acid + L-Glutamic-gamma-semialdehyde
N-Acetyl-L-glutamate 5-semialdehyde + NADP + Phosphate <> N-Acetyl-L-glutamyl 5-phosphate + Hydrogen ion + NADPH
N-Acetylornithine + Oxoglutaric acid < N-Acetyl-L-glutamate 5-semialdehyde + L-Glutamate
N-Acetyl-L-glutamate 5-semialdehyde + NADP + Inorganic phosphate > N-Acetyl-L-glutamyl 5-phosphate + NADPH
N-Acetyl-L-glutamate 5-semialdehyde + L-Glutamic acid + L-Glutamate > Oxoglutaric acid + N-Acetylornithine

Pathways:

Arginine and proline metabolism pae00330
Lysine biosynthesis pae00300
Metabolic pathways pae01100

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05fr-1900000000-cfaeff3cecd86134fd58	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-055r-6900000000-bb54f50a29e9a351858c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-02a6-9100000000-fe9c1618b7f81c2f9d5b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-f6338ed4d753ef0b744e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0m89-3900000000-b5fbc1c314380afa8cc1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9100000000-a529029ad524b613c990	View in MoNA

References

References:

Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	16319
HMDB ID	HMDB06488
Pubchem Compound ID	192878
Kegg ID	C01250
ChemSpider ID	167387
Wikipedia ID	Not Available
BioCyc ID	CPD-469
EcoCyc ID	CPD-469

N-Acetyl-L-glutamate 5-semialdehyde (PAMDB000675)

Structure for N-Acetyl-L-glutamate 5-semialdehyde (PAMDB000675)