azelaic acid   Click here for help

GtoPdb Ligand ID: 7484

Synonyms: Azelex® | Finacea® | ZK-62498
Approved drug PDB Ligand Immunopharmacology Ligand
azelaic acid is an approved drug (FDA (1995))
Compound class: Synthetic organic
Comment: Azelaic acid is a saturated dicarboxylic acid, used clinically for its antibacterial and anti-inflammatory actions, as well as for its ability to inhibit keratin and melanin production.
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 4
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 74.6
Molecular weight 188.1
XLogP 1.71
No. Lipinski's rules broken 0
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 OC(=O)CCCCCCCC(=O)O
Isomeric SMILES OC(=O)CCCCCCCC(=O)O
InChI InChI=1S/C9H16O4/c10-8(11)6-4-2-1-3-5-7-9(12)13/h1-7H2,(H,10,11)(H,12,13)
InChI Key BDJRBEYXGGNYIS-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1995))
IUPAC Name Click here for help
Nonanedioic acid
International Nonproprietary Names Click here for help
INN number INN
5883 azelaic acid
Synonyms Click here for help
Azelex® | Finacea® | ZK-62498
Database Links Click here for help
CAS Registry No. 123-99-9
ChEMBL Ligand CHEMBL1238
DrugBank Ligand DB00548
DrugCentral Ligand 270
GtoPdb PubChem SID 187051787
PubChem CID 2266
RCSB PDB Ligand AZ1
Search Google for chemical match using the InChIKey BDJRBEYXGGNYIS-UHFFFAOYSA-N
Search Google for chemicals with the same backbone BDJRBEYXGGNYIS
Search PubMed clinical trials azelaic acid
Search PubMed titles azelaic acid
Search PubMed titles/abstracts azelaic acid
UniChem Compound Search for chemical match using the InChIKey BDJRBEYXGGNYIS-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey BDJRBEYXGGNYIS-UHFFFAOYSA-N
Wikipedia Azelaic acid