L-asparagine   Click here for help

GtoPdb Ligand ID: 4533

Abbreviated name: L-Asn
PDB Ligand
Compound class: Metabolite

L-asparagine is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 3
Topological polar surface area 106.41
Molecular weight 132.05
XLogP -4.43
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES NC(=O)CC(C(=O)O)N
Isomeric SMILES NC(=O)C[C@@H](C(=O)O)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
InChI Key DCXYFEDJOCDNAF-REOHCLBHSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Albers A, Bröer A, Wagner CA, Setiawan I, Lang PA, Kranz EU, Lang F, Bröer S. (2001)
Na+ transport by the neural glutamine transporter ATA1.
Pflugers Arch, 443 (1): 92-101. [PMID:11692272]
2. Bröer S. (2006)
The SLC6 orphans are forming a family of amino acid transporters.
Neurochem Int, 48 (6-7): 559-67. [PMID:16540203]
3. Fei YJ, Sugawara M, Nakanishi T, Huang W, Wang H, Prasad PD, Leibach FH, Ganapathy V. (2000)
Primary structure, genomic organization, and functional and electrogenic characteristics of human system N 1, a Na+- and H+-coupled glutamine transporter.
J Biol Chem, 275 (31): 23707-17. [PMID:10823827]
4. Hatanaka T, Huang W, Ling R, Prasad PD, Sugawara M, Leibach FH, Ganapathy V. (2001)
Evidence for the transport of neutral as well as cationic amino acids by ATA3, a novel and liver-specific subtype of amino acid transport system A.
Biochim Biophys Acta, 1510 (1-2): 10-7. [PMID:11342143]
5. Hatanaka T, Huang W, Wang H, Sugawara M, Prasad PD, Leibach FH, Ganapathy V. (2000)
Primary structure, functional characteristics and tissue expression pattern of human ATA2, a subtype of amino acid transport system A.
Biochim Biophys Acta, 1467 (1): 1-6. [PMID:10930503]
6. Hägglund MG, Sreedharan S, Nilsson VC, Shaik JH, Almkvist IM, Bäcklin S, Wrange O, Fredriksson R. (2011)
Identification of SLC38A7 (SNAT7) protein as a glutamine transporter expressed in neurons.
J Biol Chem, 286 (23): 20500-11. [PMID:21511949]
7. Nakanishi T, Sugawara M, Huang W, Martindale RG, Leibach FH, Ganapathy ME, Prasad PD, Ganapathy V. (2001)
Structure, function, and tissue expression pattern of human SN2, a subtype of the amino acid transport system N.
Biochem Biophys Res Commun, 281 (5): 1343-8. [PMID:11243884]