P. aeruginosa Metabolome Database: N-Acetyl-L-alanine (PAMDB000272)

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

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB000272

Identification

Name:

N-Acetyl-L-alanine

Description:

N-Acetyl-L-alanine is a product that can be formed spontaneously by the reaction of pyruvate with ammonia. The enzyme phenylalanine N-acetyltransferase (EC 2.3.1.53) can also generate this molecule from Acetyl-CoA and Alanine.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

(S)-(-)-N-Acetylalanine
(S)-N-Acetylalanine
Acetyl-L-alanine
Acetylalanine
L-N-Acetylalanine
N-Acetyl-(S)-alanine
N-Acetyl-L-alanine
N-Acetylalanine

Chemical Formula:

C₅H₉NO₃

Average Molecular Weight:

131.1299

Monoisotopic Molecular Weight:

131.058243159

InChI Key:

KTHDTJVBEPMMGL-VKHMYHEASA-N

InChI:

InChI=1S/C5H9NO3/c1-3(5(8)9)6-4(2)7/h3H,1-2H3,(H,6,7)(H,8,9)/t3-/m0/s1

CAS number:

97-69-8

IUPAC Name:

(2S)-2-acetamidopropanoic acid

Traditional IUPAC Name:

N-acetylalanine

SMILES:

C[C@H](NC(C)=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
Acetamide
Secondary carboxylic acid amide
Carboxamide group
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid amide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

alanine derivative (CHEBI:40992 )
N-acetyl-L-amino acid (CHEBI:40992 )

Physical Properties

State:

Solid

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	43.6 mg/mL	ALOGPS
logP	-0.53	ALOGPS
logP	-0.76	ChemAxon
logS	-0.48	ALOGPS
pKa (Strongest Acidic)	3.89	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.4 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	29.94 m³·mol^-1	ChemAxon
Polarizability	12.49 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:

Acetyl-CoA + L-Glutamate <> N-Acetyl-L-alanine + Coenzyme A + Hydrogen ion + N-Acetylglutamic acid
N-Acetyl-L-alanine + Adenosine triphosphate + N-Acetylglutamic acid <> N-Acetyl-L-glutamyl 5-phosphate + ADP
Acetyl-CoA + L-Glutamate <> Coenzyme A + N-Acetyl-L-alanine
Adenosine triphosphate + N-Acetyl-L-alanine <> ADP + N-Acetyl-L-glutamyl 5-phosphate
Acetyl-CoA + L-Glutamic acid + L-Glutamate <> N-Acetyl-L-alanine + Coenzyme A + Hydrogen ion + N-Acetylglutamic acid + N-Acetyl-L-alanine + N-Acetylglutamic acid

Pathways:

Arginine and proline metabolism pae00330

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-05n0-2900000000-c0a5e66723f41ac78751	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS	Not Available
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0006-9000000000-4cea4517104b7a324deb	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0006-9000000000-4497242e6b422cf3f913	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0006-9000000000-22d764f7b773b82c6515	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available
1D NMR	13C NMR Spectrum	Not Available
1D NMR	1H NMR Spectrum	Not Available
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available

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

Synthesis Reference:

Vanzura, Jiri; Kasafirek, Evzen; Hrabalek, Alexandr; Vinsova, Jarmila; Krepelka, Jiri. Process for preparing highly pure N-acetyl-L- or -D-alanine. Czech. (1989), 4 pp.

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	17533
HMDB ID	HMDB00766
Pubchem Compound ID	7345
Kegg ID	Not Available
ChemSpider ID	79449
Wikipedia ID	Not Available
BioCyc ID	Not Available
Ligand Expo	AYA

N-Acetyl-L-alanine (PAMDB000272)

Structure for N-Acetyl-L-alanine (PAMDB000272)