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Identification
NameL-Asparagine
Accession NumberDB00174  (NUTR00015)
Typesmall molecule
Groupsapproved, nutraceutical
Description

A non-essential amino acid that is involved in the metabolic control of cell functions in nerve and brain tissue. It is biosynthesized from aspartic acid and ammonia by asparagine synthetase. (From Concise Encyclopedia Biochemistry and Molecular Biology, 3rd ed)

Structure
Thumb
Synonyms
SynonymLanguageCode
(2S)-2-amino-3-carbamoylpropanoic acidNot AvailableNot Available
(2S)-2,4-diamino-4-oxobutanoic acidNot AvailableNot Available
(S)-2-amino-3-carbamoylpropanoic acidNot AvailableNot Available
(S)-AsparagineNot AvailableNot Available
2-Aminosuccinamic acidNot AvailableNot Available
alpha-aminosuccinamic acidNot AvailableNot Available
AsnNot AvailableNot Available
AsparagineNot AvailableNot Available
Aspartamic acidNot AvailableNot Available
L-2-aminosuccinamic acidNot AvailableNot Available
L-aspartic acid beta-amideNot AvailableNot Available
L-aspartic acid β-amideNot AvailableNot Available
α-aminosuccinamic acidNot AvailableNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
Categories
CAS number70-47-3
WeightAverage: 132.1179
Monoisotopic: 132.053492132
Chemical FormulaC4H8N2O3
InChI KeyDCXYFEDJOCDNAF-REOHCLBHSA-N
InChI
InChI=1S/C4H8N2O3/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H2,6,7)(H,8,9)/t2-/m0/s1
IUPAC Name
(2S)-2-amino-3-carbamoylpropanoic acid
SMILES
N[C@@H](CC(N)=O)C(O)=O
Mass Specshow(2.96 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassOrganic Acids and Derivatives
ClassCarboxylic Acids and Derivatives
SubclassAmino Acids, Peptides, and Analogues
Direct parentAlpha Amino Acids and Derivatives
Alternative parentsAmino Fatty Acids; Primary Carboxylic Acid Amides; Polyamines; Carboxylic Acids; Enolates; Monoalkylamines
Substituentscarboxamide group; primary carboxylic acid amide; polyamine; enolate; carboxylic acid; amine; primary amine; primary aliphatic amine; organonitrogen compound
Classification descriptionThis compound belongs to the alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
Pharmacology
IndicationUsed for nutritional supplementation, also for treating dietary shortage or imbalance.
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 actionAsparagine, 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.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.5517
Blood Brain Barrier + 0.8465
Caco-2 permeable - 0.8457
P-glycoprotein substrate Non-substrate 0.8088
P-glycoprotein inhibitor I Non-inhibitor 0.9513
P-glycoprotein inhibitor II Non-inhibitor 0.9935
Renal organic cation transporter Non-inhibitor 0.9753
CYP450 2C9 substrate Non-substrate 0.8403
CYP450 2D6 substrate Non-substrate 0.8337
CYP450 3A4 substrate Non-substrate 0.7705
CYP450 1A2 substrate Non-inhibitor 0.9617
CYP450 2C9 substrate Non-inhibitor 0.9717
CYP450 2D6 substrate Non-inhibitor 0.9669
CYP450 2C19 substrate Non-inhibitor 0.9763
CYP450 3A4 substrate Non-inhibitor 0.9079
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9922
Ames test Non AMES toxic 0.6386
Carcinogenicity Non-carcinogens 0.8619
Biodegradation Ready biodegradable 0.8549
Rat acute toxicity 1.4003 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9979
hERG inhibition (predictor II) Non-inhibitor 0.9786
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point234-235 °CPhysProp
water solubility2.94E+004 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP-3.82CHMELIK,J ET AL. (1991)
logS-0.74ADME Research, USCD
pKa8.82 (at 18 °C)KORTUM,G ET AL (1961)
Predicted Properties
PropertyValueSource
water solubility1.68e+02 g/lALOGPS
logP-3.4ALOGPS
logP-4.3ChemAxon
logS0.1ALOGPS
pKa (strongest acidic)2ChemAxon
pKa (strongest basic)8.43ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count4ChemAxon
hydrogen donor count3ChemAxon
polar surface area106.41ChemAxon
rotatable bond count3ChemAxon
refractivity28.35ChemAxon
polarizability11.68ChemAxon
number of rings0ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraGC-MSMS/MSLC-MS1D NMR2D NMR
References
Synthesis Reference

Sang C. Park, “Pharmaceutical preparation containing L-aspartate or L-asparagine for preventing ethanol toxicity, and process for preparation thereof.” U.S. Patent US5389359, issued November, 1991.

US5389359
General ReferenceNot Available
External Links
ResourceLink
KEGG CompoundC00152
PubChem Compound6267
PubChem Substance46507804
ChemSpider6031
ChEBI17196
ChEMBLCHEMBL58832
PharmGKBPA164776968
HETASN
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSshow(72.2 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Neutral amino acid transporter B(0)

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Neutral amino acid transporter B(0) Q15758 Details

References:

  1. Dun Y, Mysona B, Itagaki S, Martin-Studdard A, Ganapathy V, Smith SB: Functional and molecular analysis of D-serine transport in retinal Muller cells. Exp Eye Res. 2007 Jan;84(1):191-9. Epub 2006 Nov 13. Pubmed
  2. Oppedisano F, Pochini L, Galluccio M, Cavarelli M, Indiveri C: Reconstitution into liposomes of the glutamine/amino acid transporter from renal cell plasma membrane: functional characterization, kinetics and activation by nucleotides. Biochim Biophys Acta. 2004 Dec 15;1667(2):122-31. Pubmed

2. Isoaspartyl peptidase/L-asparaginase

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Isoaspartyl peptidase/L-asparaginase Q7L266 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

3. Probable asparagine--tRNA ligase, mitochondrial

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Probable asparagine--tRNA ligase, mitochondrial Q96I59 Details

References:

  1. Iwasaki W, Sekine S, Kuroishi C, Kuramitsu S, Shirouzu M, Yokoyama S: Structural basis of the water-assisted asparagine recognition by asparaginyl-tRNA synthetase. J Mol Biol. 2006 Jul 7;360(2):329-42. Epub 2006 May 15. Pubmed
  2. Roy H, Becker HD, Reinbolt J, Kern D: When contemporary aminoacyl-tRNA synthetases invent their cognate amino acid metabolism. Proc Natl Acad Sci U S A. 2003 Aug 19;100(17):9837-42. Epub 2003 Jul 21. Pubmed

4. Sodium-coupled neutral amino acid transporter 3

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Sodium-coupled neutral amino acid transporter 3 Q99624 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

5. Asparagine synthetase [glutamine-hydrolyzing]

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Asparagine synthetase [glutamine-hydrolyzing] P08243 Details

References:

  1. Tesson AR, Soper TS, Ciustea M, Richards NG: Revisiting the steady state kinetic mechanism of glutamine-dependent asparagine synthetase from Escherichia coli. Arch Biochem Biophys. 2003 May 1;413(1):23-31. Pubmed
  2. Fresquet V, Thoden JB, Holden HM, Raushel FM: Kinetic mechanism of asparagine synthetase from Vibrio cholerae. Bioorg Chem. 2004 Apr;32(2):63-75. Pubmed
  3. Chaffei C, Pageau K, Suzuki A, Gouia H, Ghorbel MH, Masclaux-Daubresse C: Cadmium toxicity induced changes in nitrogen management in Lycopersicon esculentum leading to a metabolic safeguard through an amino acid storage strategy. Plant Cell Physiol. 2004 Nov;45(11):1681-93. Pubmed
  4. Al Sarraj J, Vinson C, Thiel G: Regulation of asparagine synthetase gene transcription by the basic region leucine zipper transcription factors ATF5 and CHOP. Biol Chem. 2005 Sep;386(9):873-9. Pubmed
  5. Iwamoto S, Mihara K, Downing JR, Pui CH, Campana D: Mesenchymal cells regulate the response of acute lymphoblastic leukemia cells to asparaginase. J Clin Invest. 2007 Apr;117(4):1049-57. Epub 2007 Mar 22. Pubmed

6. Asparagine--tRNA ligase, cytoplasmic

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Asparagine--tRNA ligase, cytoplasmic O43776 Details

References:

  1. Iwasaki W, Sekine S, Kuroishi C, Kuramitsu S, Shirouzu M, Yokoyama S: Structural basis of the water-assisted asparagine recognition by asparaginyl-tRNA synthetase. J Mol Biol. 2006 Jul 7;360(2):329-42. Epub 2006 May 15. Pubmed
  2. Iwamoto S, Mihara K, Downing JR, Pui CH, Campana D: Mesenchymal cells regulate the response of acute lymphoblastic leukemia cells to asparaginase. J Clin Invest. 2007 Apr;117(4):1049-57. Epub 2007 Mar 22. Pubmed

Transporters

1. Monocarboxylate transporter 10

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Monocarboxylate transporter 10 Q8TF71 Details

References:

  1. Kim DK, Kanai Y, Chairoungdua A, Matsuo H, Cha SH, Endou H: Expression cloning of a Na+-independent aromatic amino acid transporter with structural similarity to H+/monocarboxylate transporters. J Biol Chem. 2001 May 18;276(20):17221-8. Epub 2001 Feb 20. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 24, 2013 14:37