nelarabine   Click here for help

GtoPdb Ligand ID: 7090

Synonyms: 506U78 | Arranon® | Atriance®
Approved drug
nelarabine is an approved drug (FDA (2005), EMA (2007))
Compound class: Synthetic organic
Comment: This compound is a prodrug. The active metabolite is its 5'-triphosphate, ara-GTP.

nelarabine 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 7
Hydrogen bond donors 5
Rotatable bonds 3
Topological polar surface area 149.5
Molecular weight 297.11
XLogP 0.41
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 OCC1OC(C(C1O)O)n1cnc2c1[nH]c(=N)nc2OC
Isomeric SMILES OC[C@H]1O[C@H]([C@H]([C@@H]1O)O)n1cnc2c1[nH]c(=N)nc2OC
InChI InChI=1S/C11H15N5O5/c1-20-9-5-8(14-11(12)15-9)16(3-13-5)10-7(19)6(18)4(2-17)21-10/h3-4,6-7,10,17-19H,2H2,1H3,(H2,12,14,15)/t4-,6-,7+,10-/m1/s1
InChI Key IXOXBSCIXZEQEQ-UHTZMRCNSA-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/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2005), EMA (2007))
Approved drug? Yes. FDA (2005)  |  EMA (2007)
IUPAC Name Click here for help
(2R,3S,4S,5R)-2-(hydroxymethyl)-5-(2-imino-6-methoxy-3,9-dihydro-2H-purin-9-yl)oxolane-3,4-diol
International Nonproprietary Names Click here for help
INN number INN
7704 nelarabine
Synonyms Click here for help
506U78 | Arranon® | Atriance®
Database Links Click here for help
CAS Registry No. 121032-29-9
ChEMBL Ligand CHEMBL1201112
DrugBank Ligand DB01280
DrugCentral Ligand 1892
GtoPdb PubChem SID 178103668
PubChem CID 3011155
Search Google for chemical match using the InChIKey IXOXBSCIXZEQEQ-UHTZMRCNSA-N
Search Google for chemicals with the same backbone IXOXBSCIXZEQEQ
Search PubMed clinical trials nelarabine
Search PubMed titles nelarabine
Search PubMed titles/abstracts nelarabine
UniChem Compound Search for chemical match using the InChIKey IXOXBSCIXZEQEQ-UHTZMRCNSA-N
UniChem Connectivity Search for chemical match using the InChIKey IXOXBSCIXZEQEQ-UHTZMRCNSA-N
Wikipedia Nelarabine

Product suppliers

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MedChemExpress
Nelarabine (links to external site)
Cat. No. HY-13701