CHEBI:63612 - nelarabine

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ChEBI Name nelarabine
ChEBI ID CHEBI:63612
Definition A purine nucleoside in which O-methylguanine is attached to arabinofuranose via a β-N9-glycosidic bond. Inhibits DNA synthesis and causes cell death; a prodrug of 9-β-D-arabinofuranosylguanine (ara-G).
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Anonymous
Supplier Information
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Formula C11H15N5O5
Net Charge 0
Average Mass 297.26730
Monoisotopic Mass 297.107
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
InChIKey IXOXBSCIXZEQEQ-UHTZMRCNSA-N
SMILES COc1nc(N)nc2n(cnc12)[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O
Roles Classification
Biological Role(s): DNA synthesis inhibitor
Any substance that inhibits the synthesis of DNA.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
prodrug
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
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ChEBI Ontology
Outgoing nelarabine (CHEBI:63612) has functional parent 9-β-D-arabinofuranosylguanine (CHEBI:73141)
nelarabine (CHEBI:63612) has functional parent guanine (CHEBI:16235)
nelarabine (CHEBI:63612) has role antineoplastic agent (CHEBI:35610)
nelarabine (CHEBI:63612) has role DNA synthesis inhibitor (CHEBI:59517)
nelarabine (CHEBI:63612) has role prodrug (CHEBI:50266)
nelarabine (CHEBI:63612) is a β-D-arabinoside (CHEBI:38315)
nelarabine (CHEBI:63612) is a monosaccharide derivative (CHEBI:63367)
nelarabine (CHEBI:63612) is a purine nucleoside (CHEBI:26394)
IUPAC Name
9-(β-D-arabinofuranosyl)-6-methoxy-9H-purin-2-amine
INN Source
nelzarabine KEGG DRUG
Synonyms Sources
2-Amino-9-beta-D-arabinofuranosyl-6-methoxy-9H-purine ChemIDplus
Nelzarabine KEGG DRUG
Brand Name Source
Arranon DrugBank
Manual Xrefs Databases
1892 DrugCentral
D05134 KEGG DRUG
D06488 KEGG DRUG
DB01280 DrugBank
View more database links
Registry Numbers Types Sources
121032-29-9 CAS Registry Number KEGG DRUG
121032-29-9 CAS Registry Number ChemIDplus
13568768 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
18586926 PubMed citation Europe PMC
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63612 PubMed citation Europe PMC
Last Modified
22 February 2017