pegaptanib   Click here for help

GtoPdb Ligand ID: 6836

Synonyms: EYEOO1 | Macugen® | NX183 | pegaptanib sodium
Approved drug
pegaptanib is an approved drug (FDA (2004), EMA (2006))
Compound class: Synthetic organic
Comment: Note that the PubChem CID listed here represents only the backbone of the molecule and does not include the RNA oligonucleotide aptamer attached to the phosphate group. Acts as a vascular endothelial growth factor A antagonist, anti-angiogenic agent.
Pegaptanib is a 28-mer RNA aptamer that is covalently linked to two branched 20-kD polyethylene glycol (PEG) chains.
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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Click here for structure editor
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 13
Hydrogen bond donors 4
Rotatable bonds 27
Topological polar surface area 180.56
Molecular weight 541.28
XLogP 0.58
No. Lipinski's rules broken 2
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 COCCOC(=O)NC(C(=O)NCCCCCCCOP(=O)(O)C)CCCCNC(=O)OCCOC
Isomeric SMILES COCCOC(=O)N[C@H](C(=O)NCCCCCCCOP(=O)(O)C)CCCCNC(=O)OCCOC
InChI InChI=1S/C22H44N3O10P/c1-31-15-17-33-21(27)24-13-9-7-11-19(25-22(28)34-18-16-32-2)20(26)23-12-8-5-4-6-10-14-35-36(3,29)30/h19H,4-18H2,1-3H3,(H,23,26)(H,24,27)(H,25,28)(H,29,30)/t19-/m0/s1
InChI Key WLCZTRVUXYALDD-IBGZPJMESA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2004), EMA (2006))
IUPAC Name Click here for help
7-[[(2S)-2,6-bis(2-methoxyethoxycarbonylamino)hexanoyl]amino]heptoxy-methylphosphinic acid
International Nonproprietary Names Click here for help
INN number INN
8215 pegaptanib
Synonyms Click here for help
EYEOO1 | Macugen® | NX183 | pegaptanib sodium
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-9679463
Reactome Reaction Reactome logo R-HSA-9679477
Other databases
CAS Registry No. 222716-86-1
DrugBank Ligand DB04895
GtoPdb PubChem SID 178103442
PubChem CID 56603655
Search Google for chemical match using the InChIKey WLCZTRVUXYALDD-IBGZPJMESA-N
Search Google for chemicals with the same backbone WLCZTRVUXYALDD
Search PubMed clinical trials pegaptanib
Search PubMed titles pegaptanib
Search PubMed titles/abstracts pegaptanib
UniChem Compound Search for chemical match using the InChIKey WLCZTRVUXYALDD-IBGZPJMESA-N
UniChem Connectivity Search for chemical match using the InChIKey WLCZTRVUXYALDD-IBGZPJMESA-N
Wikipedia Pegaptanib