Argininosuccinic Acid
Basic information
- CAS
2387-71-5- Standard SMILES
NC(=NCCC[C@H](N)C(=O)O)N[C@@H](CC(=O)O)C(=O)O- InChIKey
KDZOASGQNOPSCU-WDSKDSINSA-N- Molecular formula
- C10H18N4O6
- Average molar mass
- 290.27 g/mol
- Monoisotopic mass
- 290.12263431
Overview
Argininosuccinic acid is an aspartic acid derivative.
Names & identifiers
- Preferred name
- Argininosuccinic Acid
- IUPAC
- (2S)-2-[[N'-[(4S)-4-amino-4-carboxybutyl]carbamimidoyl]amino]butanedioic acid
- English name
- 2-[amino-(4-amino-4-carboxy-butyl)imino-methyl]aminobutanedioic acid
- Molecular formula
- C10H18N4O6
- Molecular weight
- 290.27
Names & synonyms
ARGININOSUCCINIC ACIDL-Argininosuccinic acid2387-71-5L-Arginosuccinic acidT67NZ5MU4HDTXSID80178574Acid, ArgininosuccinicL-Aspartic acid, N-(((4-amino-4-carboxybutyl)amino)iminomethyl)-, (S)-(2S)-2-[[N'-[(4S)-4-amino-4-carboxybutyl]carbamimidoyl]amino]butanedioic acid(2S)-2-[[N'-[(4S)-4-amino-5-hydroxy-5-oxopentyl]carbamimidoyl]amino]butanedioic acid(2S)-2-(1-((4S)-4-amino-4-carboxybutyl)carbamimidamido)butanedioic acid(2S)-2-{1-[(4S)-4-amino-4-carboxybutyl]carbamimidamido}butanedioic acid
Show more names
Arginosuccinic acidArginosuccinic acid 13C4(N(omega)-L-arginino)succinic acidN-[[(S)-4-Amino-4-carboxybutyl]amino(imino)methyl]-L-aspartic acidN-[[[(S)-4-Amino-4-carboxybutyl]amino](imino)methyl]-L-aspartic acid2-[amino-(4-amino-4-carboxy-butyl)imino-methyl]aminobutanedioic acidL-Aspartic acid, N-[[[(4S)-4-amino-4-carboxybutyl]amino]iminomethyl]-
(2S)-2-((N'-((4S)-4-amino-4-carboxybutyl)carbamimidoyl)amino)butanedioic acid(2S)-2-((N'-((4S)-4-amino-5-hydroxy-5-oxopentyl)carbamimidoyl)amino)butanedioic acidRefChem:916164DTXCID40101065N-(4-Amino-4-carboxybutyl)amidino-L-aspartic Acid(2S)-2-(3-((4S)-4-amino-4-carboxybutyl)carbamimidamido)butanedioic acidN-((((4S)-4-Amino-4-Carboxybutyl)Amino)(Imino)Methyl)-L-Aspartic Acid(2S)-2-((amino-(((4S)-4-amino-4-carboxybutyl)amino)methylidene)amino)butanedioic acid
Properties
Computed structural properties
- XLogP
- -4.7
- Topological polar surface area
- 188 Ų
- Hydrogen bond donors
- 6
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 10
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 397
Experimental & physicochemical properties
Physical DescriptionSolid
Collision Cross Section
163.9 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
167.39 Ų [M+H]+ [CCS Type: DT; Method: stepped-field]
Physicochemical properties
- Boiling point
- 417.26 °C · 417.26°C (rough estimate)
- Density
- 1.28 · 1.2800 (rough estimate)
- refractive index
- 1.62 · 1.6200 (estimate)
- pka
- 1.62 · 1.62(at 25℃)
- FDA UNII
- 67 NZ5MU4H · T67NZ5MU4H
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Chemistry & industry
Pharmacology
Tissue LocationsKidney
Cellular LocationsCytoplasm
Metabolite PathwaysArginine and proline metabolism
Uses & manufacturing
UsesThis is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
Applications
UsesArgininosuccinic acid participates in the fourth step of the urea cycle, with being cleaved to arginine and fumaric acid by argininosuccinic acid lyase (ASL). Argininosuccinic acid reduces reduced glutathione (GSH) level, and increases the production of reactive oxygen species in cerebral cortex and striatum. Argininosuccinic acid causes lipid peroxidation and protein oxidation, and induces oxidative stress in the developing rat brain[1][2].
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Compound notes
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