Showing Compound N-Acetyl-L-serine (FDB000970)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:47 UTC

Update date

2019-11-26 02:55:42 UTC

Primary ID

FDB000970

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

N-Acetyl-L-serine

Description

Acetylation of the N-terminal amino acid (-NH2 acetylation) is a common protein modification in eukaryotes but is rarely encountered in prokaryotes. In mammalians,80 to 90 percent of the cytosolic proteins are subjected to an irreversible, cotranslational amino acid acetylation at their N-terminus. Acetylation of the N-terminal amino acid (-NH2 acetylation) is a common protein modification in eukaryotes but is rarely encountered in prokaryotes. In mammalians, 80 to 90 percent of the cytosolic proteins are subjected to an irreversible, cotranslational amino acid acetylation at their N-terminus. N-acetylated proteins are catabolized in the cytosol by the ATP-ubiquitin-dependent proteasomal pathway. Several types of aminoacylases can be distinguished on the basis of substrate specificity. Aminoacylase I (ACY1; EC 3.5.1.14), the most abundant type, is a soluble homodimeric zinc binding enzyme that catalyzes the formation of free aliphatic amino acids from N-acetylated precursors. It is encoded by the aminoacylase 1 gene (ACY1) on chromosome 3p21 that comprises 15 exons (OMIM 609924). Preferred substrates of ACY1 are aliphatic amino acids with a short-chain acyl moiety, especially N-acetyl-methionine. However, ACY1 can also catalyze the reverse reaction, the synthesis of acetylated amino acids. Functional aminoacylase I is crucial in the last step in this degradation as it catalyzes the hydrolysis of N-acetylated amino acids into acetate and the free amino acid. Although N-acetylation occurs in many metabolic pathways and N-acetylated metabolites are known to accumulate in several inborn errors, there are only a few reports on N-acetylated amino acids detected in urine. Identification of N-acetylated amino acids by routine GC-MS may be problematic for several reasons. The major problem is linked to the identification strategy itself. Identification of an unknown compound in mass spectrometry is usually based on comparison of its spectrum against a library of reference spectra. (PMID: 16465618, 16274666, 17723438). N-Acetyl-L-serine is found in watermelon.

CAS Number

16354-58-8

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Showing 1 to 5 of 5 entries

Predicted Properties

Property	Value	Source
Water Solubility	84.6 g/L	ALOGPS
logP	-1.4	ALOGPS
logP	-1.8	ChemAxon
logS	-0.24	ALOGPS
pKa (Strongest Acidic)	3.61	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.63 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	31.48 m³·mol⁻¹	ChemAxon
Polarizability	13.28 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

Chemical Formula

C5H9NO4

IUPAC name

2-acetamido-3-hydroxypropanoic acid

InChI Identifier

InChI=1S/C5H9NO4/c1-3(8)6-4(2-7)5(9)10/h4,7H,2H2,1H3,(H,6,8)(H,9,10)

InChI Key

JJIHLJJYMXLCOY-UHFFFAOYSA-N

Isomeric SMILES

CC(=O)NC(CO)C(O)=O

Average Molecular Weight

147.1293

Monoisotopic Molecular Weight

147.053157781

Classification

Description

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.

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-alpha amino acids

Alternative Parents

Substituents

N-acyl-alpha-amino acid
Serine or derivatives
Beta-hydroxy acid
Hydroxy acid
Acetamide
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid
Monocarboxylic acid or derivatives
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Alcohol
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Primary alcohol
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 40.82%; H 6.17%; N 9.52%; O 43.50%	DFC
Melting Point	Mp 207.6°	DFC
Optical Rotation	[a]22D -205 (c, 1 in MeOH)	DFC

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	N-Acetyl-L-serine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9200000000-3fdf2264d7f6bfa966ae	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f7k-1900000000-8fd08db8763ca780a73b	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0nn9-9500000000-5ed0dd34b41fd175f669	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9100000000-2e1c11fb421c1111b011	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-2900000000-0c8c866ca02199eba95d	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0zgj-9800000000-fb156ef161572da8f131	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9100000000-a9df8ace176575dd53e5	2016-09-12	View Spectrum