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SGI-110

CAT: 1410-M16656Size: 1 EachDry Ice: NoHazardous: No
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Description
A novel DNA hypomethylating dinucleotide that inhibits DNA methyltransferase (DNMT) .
CAS Number
929901-49-5
Stability
≥ 2 years
Purity
>98% (HPLC)
Weight
557.41
Molecular Formula
C18H24N9O10P
Notes
Research use only, not for human use.
Receptor
DNMT

Chemical Information

Guadecitabine

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.

CAS Number929901-49-5
PubChem CID135564655
IUPAC Name[(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 FormulaC18H24N9O10P
Molecular Weight557.4
XLogP-4.6
Topological Polar Surface Area271
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count12
Rotatable Bond Count8
Heavy Atom Count38
Formal Charge0
Complexity1110
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)O
InChI
InChI=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
InChIKey
GUWXKKAWLCENJA-WGWHJZDNSA-N
Chemical Structure
2D Structure
2D structure of Guadecitabine
CAS: 929901-49-5
CID: 135564655
Formula: C18H24N9O10P
MW: 557.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight557.4
XLogP3-4.6
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count12
Rotatable Bond Count8
Exact Mass557.13837499
Monoisotopic Mass557.13837499
Topological Polar Surface Area271 Ų
Heavy Atom Count38
Formal Charge0
Complexity1110
Isotope Atom Count0
Defined Atom Stereocenter Count6
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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