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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-AsparaginNot AvailableNot Available
L-AsparagineNot AvailableNot Available
L-aspartic acid beta-amideNot AvailableNot Available
L-aspartic acid β-amideNot AvailableNot Available
NNot AvailableNot Available
α-aminosuccinamic acidNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot 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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Amino fatty acid
  • Fatty acyl
  • Fatty acid
  • Fatty amide
  • Primary carboxylic acid amide
  • Carboxamide group
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
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
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Canavan DiseaseDiseaseSMP00175
Clomocycline Action PathwayDrug actionSMP00262
Clarithromycin Action PathwayDrug actionSMP00248
Kanamycin Action PathwayDrug actionSMP00255
Demeclocycline Action PathwayDrug actionSMP00290
Minocycline Action PathwayDrug actionSMP00292
Troleandomycin Action PathwayDrug actionSMP00730
Roxithromycin Action PathwayDrug actionSMP00251
Amikacin Action PathwayDrug actionSMP00253
Spectinomycin Action PathwayDrug actionSMP00258
Lymecycline Action PathwayDrug actionSMP00295
Lincomycin Action PathwayDrug actionSMP00728
Azithromycin Action PathwayDrug actionSMP00247
Gentamicin Action PathwayDrug actionSMP00254
Streptomycin Action PathwayDrug actionSMP00259
Chloramphenicol Action PathwayDrug actionSMP00729
Ammonia RecyclingMetabolicSMP00009
Aspartate MetabolismMetabolicSMP00067
Erythromycin Action PathwayDrug actionSMP00250
Telithromycin Action PathwayDrug actionSMP00252
Netilmicin Action PathwayDrug actionSMP00257
Tetracycline Action PathwayDrug actionSMP00294
Tigecycline Action PathwayDrug actionSMP00712
Paromomycin Action PathwayDrug actionSMP00714
Methacycline Action PathwayDrug actionSMP00727
HypoacetylaspartiaDiseaseSMP00192
Clindamycin Action PathwayDrug actionSMP00249
Neomycin Action PathwayDrug actionSMP00256
Doxycycline Action PathwayDrug actionSMP00291
Oxytetracycline Action PathwayDrug actionSMP00293
Tobramycin Action PathwayDrug actionSMP00711
Arbekacin Action PathwayDrug actionSMP00713
Rolitetracycline Action PathwayDrug actionSMP00726
Josamycin Action PathwayDrug actionSMP00731
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.5517
Blood Brain Barrier+0.8465
Caco-2 permeable-0.8457
P-glycoprotein substrateNon-substrate0.8088
P-glycoprotein inhibitor INon-inhibitor0.9513
P-glycoprotein inhibitor IINon-inhibitor0.9935
Renal organic cation transporterNon-inhibitor0.9753
CYP450 2C9 substrateNon-substrate0.8403
CYP450 2D6 substrateNon-substrate0.8337
CYP450 3A4 substrateNon-substrate0.7705
CYP450 1A2 substrateNon-inhibitor0.9617
CYP450 2C9 substrateNon-inhibitor0.9717
CYP450 2D6 substrateNon-inhibitor0.9669
CYP450 2C19 substrateNon-inhibitor0.9763
CYP450 3A4 substrateNon-inhibitor0.9079
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9922
Ames testNon AMES toxic0.6386
CarcinogenicityNon-carcinogens0.8619
BiodegradationReady biodegradable0.8549
Rat acute toxicity1.4003 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9979
hERG inhibition (predictor II)Non-inhibitor0.9786
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 Solubility168.0 mg/mLALOGPS
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 Area106.41 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity28.35 m3·mol-1ChemAxon
Polarizability11.68 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (2.96 KB)
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
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSDownload (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. 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

3. 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

4. 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

5. 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

6. 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

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