Guadecitabine
[(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 phosphate
Molecular Identity
Guadecitabine
[(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 phosphate
PubChem CID: 135564655
Guadecitabine 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.
2D Structure
Properties
C18H24N9O10P
Molecular Formula
557.40
Molecular Weight
g/mol
557.1384
Exact Mass
Da
-4.6
XLogP
Drug-like (Lipinski: < 5)
271
TPSA
May have limited oral absorption
6
H-Bond Donors
12
H-Bond Acceptors
1110
Complexity
SMILES
Canonical SMILES
SMILES: C1C(C(OC1N2C=NC3=C2N=C(NC3=O)N)COP(=O)(O)OC4CC(OC4CO)N5C=NC(=NC5=O)N)OIsomeric SMILES
SMILES: C1[C@@H]([C@H](O[C@H]1N2C=NC3=C2N=C(NC3=O)N)COP(=O)(O)O[C@H]4C[C@@H](O[C@@H]4CO)N5C=NC(=NC5=O)N)OSynonyms(20)
Guadecitabine929901-49-5SGI-110 free acid2KT4YN1DP7GuadecitabinaGuanosine, 2'-deoxy-5-azacytidylyl-(3'-5')-2'-deoxy-guadecitabinum(((2R,3S,5R)-5-(4-amino-2-oxo-1,2-dihydro-1,3,5-triazin-1-yl)-2-(hydroxymethyl)oxolan-3-yl)oxy)((((2R,3S,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3-hydroxyoxolan-2-yl)methoxy))phosphinic acid{[(2R,3S,5R)-5-(4-amino-2-oxo-1,2-dihydro-1,3,5-triazin-1-yl)-2-(hydroxymethyl)oxolan-3-yl]oxy}({[(2R,3S,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy})phosphinic acidRefChem:782753DNMT inhibitor SGI-110834-443-3SGI-110[(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 phosphateSGI 110
Data from PubChem (NCBI)
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