CHEBI:28680 - cytarabine

Main ChEBI Ontology Automatic Xrefs Reactions Pathways
ChEBI Name cytarabine
ChEBI ID CHEBI:28680
Definition A pyrimidine nucleoside in which cytosine is attached to D-arabinofuranose via a β-N1-glycosidic bond.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:40824, CHEBI:4074, CHEBI:23532
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Formula C9H13N3O5
Net Charge 0
Average Mass 243.21674
InChI InChI=1S/C9H13N3O5/c10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13)17-8/h1-2,4,6-8,13-15H,3H2,(H2,10,11,16)/t4-,6-,7+,8-/m1/s1
InChIKey UHDGCWIWMRVCDJ-CCXZUQQUSA-N
SMILES Nc1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O)c(=O)n1
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.
antiviral agent
A substance that destroys or inhibits replication of viruses.
immunosuppressive agent
An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
immunosuppressive agent
An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
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ChEBI Ontology
Outgoing cytarabine (CHEBI:28680) has functional parent cytosine (CHEBI:16040)
cytarabine (CHEBI:28680) has role antimetabolite (CHEBI:35221)
cytarabine (CHEBI:28680) has role antineoplastic agent (CHEBI:35610)
cytarabine (CHEBI:28680) has role antiviral agent (CHEBI:22587)
cytarabine (CHEBI:28680) has role immunosuppressive agent (CHEBI:35705)
cytarabine (CHEBI:28680) is a β-D-arabinoside (CHEBI:38315)
cytarabine (CHEBI:28680) is a monosaccharide derivative (CHEBI:63367)
cytarabine (CHEBI:28680) is a pyrimidine nucleoside (CHEBI:26440)
IUPAC Name
4-amino-1-β-D-arabinofuranosylpyrimidin-2(1H)-one
Synonyms Sources
1-beta-D-Arabinofuranosylcytosine ChemIDplus
4-Amino-1-beta-D-arabinofuranosyl-2(1H)-pyrimidinone ChemIDplus
Cytarabine KEGG COMPOUND
Cytosine arabinoside KEGG COMPOUND
Cytosine-1-beta-D-arabinofuranoside KEGG COMPOUND
cytosine-β-D-arabinofuranoside ChEBI
Database Links Databases
C02961 KEGG COMPOUND
Cytarabine Wikipedia
D00168 KEGG DRUG
DB00987 DrugBank
HMDB15122 HMDB
LSM-5470 LINCS
View more database links
Registry Numbers Types Sources
147-94-4 CAS Registry Number KEGG COMPOUND
147-94-4 CAS Registry Number ChemIDplus
89175 Beilstein Registry Number Beilstein
89175 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
15492802 PubMed citation CiteXplore
Last Modified
25 February 2016