Basic information
- CAS
70-47-3- Standard SMILES
NC(=O)C[C@H]([NH3+])C(=O)[O-]- InChIKey
DCXYFEDJOCDNAF-REOHCLBHSA-N- Molecular formula
- C4H8N2O3
- Average molar mass
- 132.12 g/mol
- Monoisotopic mass
- 132.05349212
Overview
L-asparagine zwitterion is zwitterionic form of L-asparagine arising from transfer of a proton from the carboxy to the amino group; major species at pH 7.3. It is a tautomer of a L-asparagine.
Names & identifiers
- Preferred name
- (2S)-4-amino-2-ammonio-4-oxobutanoate
- IUPAC
- (2S)-4-amino-2-azaniumyl-4-oxobutanoate
- English name
- L-Asparagine
- Molecular formula
- C4H8N2O3
- Molecular weight
- 132.12
Names & synonyms
(2S)-4-amino-2-ammonio-4-oxobutanoateL-asparatamineL-asparagine zwitterionCHEBI:58048(2S)-2-ammonio-3-carbamoylpropanoate(2S)-2-azaniumyl-3-carbamoylpropanoateASNASPARAGINEH-ASN-OHL-AsnCrystal VI(S)-2,4-Diamino-4-oxobutanoic acid
Show more names
Asn-OHL-Asn-OHAsparamide(2S)-2,4-Diamino-4-oxobutanoic acid
Database identifiers
- CAS
70-47-3- PubChem CID
- 6992089
- ChEBI
CHEBI:58048
Properties
Computed structural properties
- XLogP
- -2.8
- Topological polar surface area
- 111 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 9
- Formal charge
- 0
- Complexity
- 128
Experimental & physicochemical properties
LogP-3.82
Solubility29.4 mg/mL
Melting Point
234-235 °C
234 - 235 °C
Physical DescriptionSolid
Dissociation Constants8.82 (at 18 °C)
Physicochemical properties
- Melting point
- 235 °C · 235 °C (dec.) (lit.)
- alpha
- 34.5 · 34.5 º (c=10, 2N HCl)
- Boiling point
- 244.01 °C · 244.01°C (rough estimate)
- Density
- 1 · 1,543g/cm
- refractive index
- 1.488 · 1.4880 (estimate)
- storage temp.
- Keep in dark place,Inert atmosphere,Room temperature
- solubility
- Practically insoluble in methanol, ethanol, ether, benzene. Soluble in acids and alkalies.
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- F
- 3-10
- wgk
- 3
- tsca
- TSCA listed
- ridadr
- UN 2811 6.1 / PGIII
- hs_code
- 29241900
- risk_code
- 20/21/22-36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 24/25-36-26
- hazard_class
- IRRITANT
- Storage Class
- 13 - Non Combustible Solids
- Hazard statements
- H315-H319-H335
- REACH Registrations
- Active
- Precautionary statements
- P261-P305+P351+P338
- Hazardous Substances Data
- 70-47-3(Hazardous Substances Data)
Chemistry & industry
Pharmacology
PharmacodynamicsA non-essential amino acid. Asparagine is critical for the production of the body's proteins, enzymes and muscle tissue. Supplements of this amino acid are claimed to balance nervous system function.
Mechanism of Action
Asparagine, a non-essential amino acid is important in the metabolism of toxic ammonia in the body through the action of asparagine synthase which attaches ammonia to aspartic acid in an amidation reaction. Asparagine is also used as a structural component in many proteins.
Tissue LocationsAll Tissues
Cellular LocationsCytoplasm
Metabolite PathwaysAmikacin Action Pathway
Applications
DescriptionAsparagine (abbreviated as Asn or N) is one of the 20 most common natural amino acids on Earth. It has carboxamide as the sidechain's functional group. It is not an essential amino acid. Its codons are AAU and AAC. The amino acid L-asparagine is a structural analog of L-aspartic acid, where the side chain of the carboxylic acid moiety is amidated, to give a terminal amine group. This renders L-asparagine neutral at physiological pH. The amide group of asparagine is derived from glutamate, in the reaction of aspartate and glutamine in the presence of ATP to yield asparagine and glutamate. In vivo, asparagine is hydrolyzed to aspartate and NH4+ by asparaginase. Asparagine is also an important amino acid in glycopeptide bonds, via N-glycosyl linkages to the sugar rings.
OccurrenceDietary sourcesAsparagine is not essential for humans, which means that it can be synthesized from central metabolic pathway intermediates and is not required in the diet. Asparagine is found in : Animal sources : dairy, whey, beef, poultry, eggs, fish, lactalbumin , sea food Plant sources : asparagus, potatoes, legumes, nuts, seeds, soy, whole grains.BiosynthesisThe precursor to asparagine is oxaloacetate. Oxaloacetate is converted to aspartate using a transaminase enzyme. The enzyme transfers the amino group from glutamate to oxaloacetate producing α- ketoglutarate and aspartate. The enzyme asparagine synthetase produces asparagine, AMP, glutamate, and pyrophosphate from aspartate, glutamine, and ATP. In the asparagine synthetase reaction, ATP is used to activate aspartate, forming β-aspartyl-AMP. Glutamine donates an ammonium group, which reacts with β-aspartyl-AMP to form asparagine and free AMP.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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