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Cytarabine 5′-monophosphate

CAT: 0013-GTR19232528-01Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0013-GTR19232528-01Size:5 mg
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Description
Cytarabine 5′-monophosphate (ara-CMP) is the active phosphorylated metabolite of the antimetabolite cytarabine. It functions by incorporating into DNA via DNA polymerase α, thereby inhibiting DNA replication. This mechanism has demonstrated efficacy in research models, including the inhibition of yeast replication in vitro and improved survival in murine leukemia studies in vivo.
CAS Number
7075-11-8
Field of Research
Cell Biology, Metabolism Research, Molecular Biology, Pharmacology & Drug Discovery
Smiles
Nc1ccn ([C@@H]2O[C@H] (COP (O) (O) =O) [C@@H] (O) [C@@H]2O) c (=O) n1
Molecular Formula
C9H14N3O8P
Molecular Weight
323.198
Storage Conditions
-20°C
Notes
For research use only.

Chemical Information

Ara-5'-cmp
CAS Number7075-11-8
PubChem CID65177
IUPAC Name[(2R,3S,4S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
Molecular FormulaC9H14N3O8P
Molecular Weight323.20
XLogP-3.4
Topological Polar Surface Area175
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count8
Rotatable Bond Count4
Heavy Atom Count21
Formal Charge0
Complexity531
SMILES
C1=CN(C(=O)N=C1N)[C@H]2[C@H]([C@@H]([C@H](O2)COP(=O)(O)O)O)O
InChI
InChI=1S/C9H14N3O8P/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H2,10,11,15)(H2,16,17,18)/t4-,6-,7+,8-/m1/s1
InChIKey
IERHLVCPSMICTF-CCXZUQQUSA-N
Chemical Structure
2D Structure
2D structure of Ara-5'-cmp
CAS: 7075-11-8
CID: 65177
Formula: C9H14N3O8P
MW: 323.20
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight323.20
XLogP3-3.4
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count8
Rotatable Bond Count4
Exact Mass323.05185141
Monoisotopic Mass323.05185141
Topological Polar Surface Area175 Ų
Heavy Atom Count21
Formal Charge0
Complexity531
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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