ChemFOnt: Showing chemical card for N-alpha-Acetyl-L-citrulline (CFc000000682)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:08 UTC

Chemfont ID

CFc000000682

Molecule Identification

Common Name

N-alpha-Acetyl-L-citrulline

Definition

N-alpha-Acetyl-L-citrulline, also known as N-acetylcitrulline, is an N-acetylated metabolite of citrulline that is part of the arginine biosynthetic pathway. Arginine biosynthesis is notable for its complexity and variability at the genetic level, and by its connection with several other pathways, such as pyrimidine and polyamine biosynthesis, and certain degradative pathways. The initial steps of the arginine biosynthetic pathways proceed via N-acetylated intermediates. The presumed reason for this is that the acetylation prevents the spontaneous cyclization of glutamate derivatives, which leads to proline biosynthesis. N-acetyl-L-ornithine can be transcarbamylated directly by the enzyme acetylornithine transcarbamylase, resulting in N-acetyl-L-citrulline. The enzyme acetylornithine deacetylase can accept N-acetyl-L-citrulline as a substrate and can deacetylate it into citrulline. N-alpha-Acetyl-L-citrulline is found in cases of deficiency of the urea cycle enzyme argininosuccinate synthase (EC 6.3.4.5) that leads to increased concentrations of citrulline and N-acetylcitrulline in the urine (PMID: 14633929 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-(Acetylamino)-5-[(aminocarbonyl)amino]pentanoic acid	ChEBI
2-(Acetylamino)-5-[(aminocarbonyl)amino]pentanoate	Generator
(2S)-2-(acetylamino)-5-[(Aminocarbonyl)amino]pentanoate	HMDB
(2S)-2-(acetylamino)-5-[(Aminocarbonyl)amino]pentanoic acid	HMDB
(2S)-2-acetamido-5-(carbamoylamino)Pentanoate	HMDB
(2S)-2-acetamido-5-(carbamoylamino)Pentanoic acid	HMDB
(S)-2-acetamido-5-Ureidopentanoate	HMDB
(S)-2-acetamido-5-Ureidopentanoic acid	HMDB
a-N-Acetylcitrulline	HMDB
alpha-N-Acetylcitrulline	HMDB
N-Acetyl citrulline	HMDB
N-Acetyl-L-citrulline	HMDB
N-alpha-Acetylcitrulline	HMDB
N2-Acetyl-N5-carbamoyl-L-ornithine	HMDB
Na-acetyl-L-citrulline	HMDB
OLN	HMDB
N-a-Acetylcitrulline	Generator
N-Α-acetylcitrulline	Generator

Chemical Formula

C₈H₁₅N₃O₄

Average Molecular Weight

217.2224

Monoisotopic Molecular Weight

217.106255983

IUPAC Name

5-(carbamoylamino)-2-acetamidopentanoic acid

Traditional Name

N-acetylcitrulline

CAS Registry Number

33965-42-3

SMILES

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

InChI Identifier

InChI=1S/C8H15N3O4/c1-5(12)11-6(7(13)14)3-2-4-10-8(9)15/h6H,2-4H2,1H3,(H,11,12)(H,13,14)(H3,9,10,15)

InChI Key

WMQMIOYQXNRROC-UHFFFAOYSA-N

Chemical Taxonomy

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
Fatty acid
Acetamide
Carboxamide group
Carbonic acid derivative
Secondary carboxylic acid amide
Urea
Carboxylic acid
Monocarboxylic acid or derivatives
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

ureas (CHEBI:49006 )
monocarboxylic acid (CHEBI:49006 )
N-acetyl-amino acid (CHEBI:49006 )

Functional Ontology

Not Available

Feces (PMID: 27543620)

Cellular substructure

Cytoplasm (HMDB: HMDB0000856)

Source

Endogenous

Endogenous (HMDB: HMDB0000856)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	3.57 g/L	ALOGPS
logP	-2	ALOGPS
logP	-1.9	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	3.87	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	121.52 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	50.77 m³·mol⁻¹	ChemAxon
Polarizability	21.5 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022282

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11506771

PDB ID

Not Available

ChEBI ID

49006

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Shi, Dashuang; Morizono, Hiroki; Yu, Xiaolin; Roth, Lauren; Caldovic, Ljubica; Allewell, Norma M.; Malamy, Michael H.; Tuchman, Mendel. Crystal Structure of N-Acetylornithine Transcarbamylase from Xanthomonas campestris: A novel enzyme in a new arginine biosynthetic pathway found in several eubacteria. Journal of Biological Chemistry (2005), 280(15), 14366-14369. (Biosynthetic preparation)

Showing chemical card for N-alpha-Acetyl-L-citrulline (CFc000000682)

MOL for CFc000000682 (N-alpha-Acetyl-L-citrulline)

3D MOL for CFc000000682 (N-alpha-Acetyl-L-citrulline)

3D SDF for CFc000000682 (N-alpha-Acetyl-L-citrulline)

3D-SDF for CFc000000682 (N-alpha-Acetyl-L-citrulline)

PDB for CFc000000682 (N-alpha-Acetyl-L-citrulline)

3D PDB for CFc000000682 (N-alpha-Acetyl-L-citrulline)

SMILES for CFc000000682 (N-alpha-Acetyl-L-citrulline)

INCHI for CFc000000682 (N-alpha-Acetyl-L-citrulline)

Structure for CFc000000682 (N-alpha-Acetyl-L-citrulline)

3D Structure for CFc000000682 (N-alpha-Acetyl-L-citrulline)