L-aspartic acid   Click here for help

GtoPdb Ligand ID: 3309

Synonyms: L-Asp | L-aspartate
PDB Ligand
Compound class: Metabolite
Comment: This ligand entry also represents L-aspartate (CHEBI:29993), the carboxylate anion and salt form of the acid. It is in the aspartate form that the ligand is transported across cell membranes.

L-aspartic acid is commercially available from our sponsors

2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. 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.

✖
Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 3
Topological polar surface area 100.62
Molecular weight 133.04
XLogP -3.71
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help

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.

✖
Canonical SMILES OC(=O)CC(C(=O)O)N
Isomeric SMILES OC(=O)C[C@@H](C(=O)O)N
InChI InChI=1S/C4H7NO4/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H,6,7)(H,8,9)/t2-/m0/s1
InChI Key CKLJMWTZIZZHCS-REOHCLBHSA-N
Natural/Endogenous Targets
Target
GluN1
GluN2A
GluN2B
GluN2C
GluN2D
Enzymes Catalysing Reactions with this Compound as a Substrate or Product
Enzyme EC number Reaction Reference
Glutamic acid decarboxylase 1
Glutamic acid decarboxylase 2
Transporters Moving this Compound Across a Lipid Membrane
Transporter EC number Reaction Reference
Excitatory amino acid transporter 1
Excitatory amino acid transporter 2
Excitatory amino acid transporter 3
Excitatory amino acid transporter 4
Excitatory amino acid transporter 5
Cation-chloride cotransporter 9
Sialin 2
AGC1
AGC2
Selectivity at ion channels
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
GluN1 Ligand is endogenous in the given species Hs Agonist Agonist - - -
⤷ [Binds to: glutamate site]
GluN2A Ligand is endogenous in the given species Hs Agonist Agonist - - -
⤷ [Binds to: glutamate site] GluN2D = GluN2B > GluN2C = GluN2A
GluN2B Ligand is endogenous in the given species Hs Agonist Agonist - - -
⤷ [Binds to: glutamate site] GluN2D = GluN2B > GluN2C = GluN2A
GluN2C Ligand is endogenous in the given species Hs Agonist Agonist - - -
⤷ [Binds to: glutamate site] GluN2D = GluN2B > GluN2C = GluN2A
GluN2D Ligand is endogenous in the given species Hs Agonist Agonist - - -
⤷ [Binds to: glutamate site] GluN2D = GluN2B > GluN2C = GluN2A
Additional information and targets (data relate to human unless otherwise stated)
Description Data Reference
Amino-acid rank order of potency at CaS receptor L-phenylalanine, L-tryptophan, L-histidine > L-alanine > L-serine, L-proline, L-glutamic acid > L-aspartic acid (not L-lysine, L-arginine, L-leucine and L-isoleucine) 1
Targets where the ligand is described in the comment field
Target Comment
Glutamic acid decarboxylase 1 in Decarboxylases
Glutamic acid decarboxylase 1 in GABA turnover
 L-aspartic acid is a less rapidly metabolised substrate of mouse brain glutamic acid decarboxylase generating β-alanine [3]. Autoantibodies against GAD1 and GAD2 are elevated in type 1 diabetes mellitus and neurological disorders (see Further reading).
Glutamic acid decarboxylase 2 in Decarboxylases
Glutamic acid decarboxylase 2 in GABA turnover
 L-aspartic acid is a less rapidly metabolised substrate of mouse brain glutamic acid decarboxylase generating β-alanine [3]. Autoantibodies against GAD1 and GAD2 are elevated in type 1 diabetes mellitus and neurological disorders (see Further reading).