CHEBI:490877 - didanosine

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ChEBI Name didanosine
ChEBI ID CHEBI:490877
Definition A purine 2',3'-dideoxyribonucleoside that is inosine in which the hydroxy groups at both the 2' and the 3' positions on the sugar moiety have been replaced by hydrogen. An antiviral drug, it is used as a medication to treat HIV/AIDS.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:668806, CHEBI:158219, CHEBI:39738, CHEBI:475381, CHEBI:4516
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Formula C10H12N4O3
Net Charge 0
Average Mass 236.22730
Monoisotopic Mass 236.091
InChI InChI=1S/C10H12N4O3/c15-3-6-1-2-7(17-6)14-5-13-8-9(14)11-4-12-10(8)16/h4-7,15H,1-3H2,(H,11,12,16)/t6-,7+/m0/s1
InChIKey BXZVVICBKDXVGW-NKWVEPMBSA-N
SMILES OC[C@@H]1CC[C@@H](O1)n1cnc2c1nc[nH]c2=O
Roles Classification
Biological Role(s): antimetabolite
A substance which is structurally similar to a metabolite but which competes with it or replaces it, and so prevents or reduces its normal utilization.
HIV-1 reverse transcriptase inhibitor
An entity which inhibits the activity of HIV-1 reverse transcriptase.
antiviral drug
A substance used in the prophylaxis or therapy of virus diseases.
EC 2.4.2.1 (purine-nucleoside phosphorylase) inhibitor
An EC 2.4.2.* (pentosyltransferase) inhibitor that interferes with the action of purine nucleoside phosphorylase (EC 2.4.2.1).
Application(s): antiviral drug
A substance used in the prophylaxis or therapy of virus diseases.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing didanosine (CHEBI:490877) has role antimetabolite (CHEBI:35221)
didanosine (CHEBI:490877) has role antiviral drug (CHEBI:36044)
didanosine (CHEBI:490877) has role EC 2.4.2.1 (purine-nucleoside phosphorylase) inhibitor (CHEBI:63090)
didanosine (CHEBI:490877) has role HIV-1 reverse transcriptase inhibitor (CHEBI:53756)
didanosine (CHEBI:490877) is a purine 2',3'-dideoxyribonucleoside (CHEBI:48442)
IUPAC Name
2',3'-dideoxyinosine
INNs Sources
didanosina ChemIDplus
didanosine ChemIDplus
didanosinum ChemIDplus
Synonyms Sources
2,3-dideoxyinosine ChEMBL
9-((2R,5S)-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-1H-purin-6(9H)-one ChEMBL
9-((2R,5S)-5-Hydroxymethyl-tetrahydro-furan-2-yl)-1,9-dihydro-purin-6-one ChEMBL
9-((2S,5R)-5-Hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-ol ChEMBL
9-[(2R,5S)-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1,9-dihydro-6H-purin-6-one IUPAC
DDI DrugBank
ddI ChemIDplus
ddIno ChEBI
Didanosine KEGG COMPOUND
dideoxyinosine ChemIDplus
Manual Xrefs Databases
2DI PDBeChem
869 DrugCentral
C06953 KEGG COMPOUND
D00296 KEGG DRUG
DB00900 DrugBank
Didanosine Wikipedia
EP206497 Patent
LSM-6017 LINCS
View more database links
Registry Numbers Types Sources
3619529 Reaxys Registry Number Reaxys
3619529 Beilstein Registry Number Beilstein
69655-05-6 CAS Registry Number KEGG COMPOUND
69655-05-6 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
10386939 PubMed citation ChEMBL
1619614 PubMed citation ChEMBL
17046264 PubMed citation ChEMBL
18549801 PubMed citation Europe PMC
29438107 PubMed citation Europe PMC
Last Modified
15 June 2018
General Comment
2011-03-24 Replacing the 2' and 3'-hydroxy groups of inosine by hydrogen prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. Didanosine is thus a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA by binding to reverse transcriptase, and is used in the treatment of HIV infection, usually with other antiretrovirals as part of combination therapy.