sialic acid   Click here for help

GtoPdb Ligand ID: 4644

Synonyms: aceneuramic acid | N-acetylneuraminic acid
PDB Ligand
Compound class: Metabolite or derivative
Comment: The structure shown above is representative of this class of compounds. For more details see the entry in ChEBI linked to above.
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 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.

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Hydrogen bond acceptors 10
Hydrogen bond donors 7
Rotatable bonds 10
Topological polar surface area 184.62
Molecular weight 309.11
XLogP -4.46
No. Lipinski's rules broken 1
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.

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Canonical SMILES OCC(C(C(C(C(CC(=O)C(=O)O)O)NC(=O)C)O)O)O
Isomeric SMILES OC[C@H]([C@H]([C@@H]([C@@H]([C@H](CC(=O)C(=O)O)O)NC(=O)C)O)O)O
InChI InChI=1S/C11H19NO9/c1-4(14)12-8(5(15)2-6(16)11(20)21)10(19)9(18)7(17)3-13/h5,7-10,13,15,17-19H,2-3H2,1H3,(H,12,14)(H,20,21)/t5-,7+,8+,9+,10+/m0/s1
InChI Key KBGAYAKRZNYFFG-BOHATCBPSA-N
Classification Click here for help
Compound class Metabolite or derivative
IUPAC Name Click here for help
(4S,5R,6R,7S,8R)-5-acetamido-4,6,7,8,9-pentahydroxy-2-oxononanoic acid
Synonyms Click here for help
aceneuramic acid | N-acetylneuraminic acid
Database Links Click here for help
ChEBI CHEBI:26667
ChEMBL Ligand CHEMBL2105945
GtoPdb PubChem SID 178101361
PubChem CID 14017587
RCSB PDB Ligand SI3
Search Google for chemical match using the InChIKey KBGAYAKRZNYFFG-BOHATCBPSA-N
Search Google for chemicals with the same backbone KBGAYAKRZNYFFG
UniChem Compound Search for chemical match using the InChIKey KBGAYAKRZNYFFG-BOHATCBPSA-N
UniChem Connectivity Search for chemical match using the InChIKey KBGAYAKRZNYFFG-BOHATCBPSA-N
Wikipedia Sialic_acid