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CHEBI:231603 - guadecitabine

Default Structure
ChEBI IDCHEBI:231603
ChEBI Nameguadecitabine
Stars
DefinitionGuadecitabine is a dinucleotide antimetabolite composed of a decitabine linked via phosphodiester bond to a deoxyguanosine, with potential antineoplastic activity. Following metabolic activation via cleavage of the phosphodiester bond and incorporation of the decitabine moiety into DNA, guadecitabine inhibits DNA methyltransferase, thereby causing non-specific, genome-wide hypomethylation, and induction of cell cycle arrest at S-phase. This agent is resistant to cytidine deaminase, which may result in gradual release of decitabine both extra- and intra-cellularly, leading to prolonged exposure to decitabine.
Submitterruixy
DownloadsMolfile
FormulaC18H24N9O10P
Net Charge0
Average Mass557.417
Monoisotopic Mass557.13837
SMILES[H][C@]1(n2cnc(=N)nc2O)C[C@]([H])(OP(=O)(O)OC[C@@]2([H])O[C@@]([H])(n3cnc4c(O)nc(=N)nc43)C[C@]2([H])O)[C@@]([H])(CO)O1
InChIInChI=1S/C18H24N9O10P/c19-16-22-6-27(18(31)25-16)12-2-8(9(3-28)35-12)37-38(32,33)34-4-10-7(29)1-11(36-10)26-5-21-13-14(26)23-17(20)24-15(13)30/h5-12,28-29H,1-4H2,(H,32,33)(H2,19,25,31)(H3,20,23,24,30)/t7-,8-,9+,10+,11+,12+/m0/s1
InChIKeyGUWXKKAWLCENJA-WGWHJZDNSA-N
ChEBI Ontology
Outgoing Relation(s)
guadecitabine (CHEBI:231603) is a organic molecular entity (CHEBI:50860)
Synonyms  Source
2KT4YN1DP7SUBMITTER
[(2R,3S,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methyl [(2R,3S,5R)-5-(4-amino-2-oxo-1,3,5-triazin-1-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphateSUBMITTER
SGI-110SUBMITTER
Registry NumbersSources
CAS:929901-49-5SUBMITTER