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Cytarabine 5’-monophosphate

CAT: 0804-HY-W344074-01Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-W344074-01Size:5 mg
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Description
Cytarabine 5′-monophosphate is a metabolite of the nucleoside analog Cytarabine , catalyzed by deoxycytidine kinase. Cytarabine 5′-monophosphate is incorporated into DNA by DNA polymerase α, which reduces the rate of DNA synthesis. At a concentration of 15 mM, Cytarabine 5′-monophosphate inhibits nuclear and mitochondrial DNA replication in Saccharomyces cerevisiae (S. cerevisiae). Additionally, Cytarabine 5′-monophosphate (3.5-75.1 mg/kg) improves survival in leukemia mice (L1210 mice). Cytarabine 5′-monophosphate can be used in cancer research[1].
CAS Number
7075-11-8
UNSPSC
12352005
Hazard Statement
H302-H315-H319-H335
Target
DNA/RNA Synthesis; Drug Metabolite
Related Pathways
Cell Cycle/DNA Damage; Metabolic Enzyme/Protease
Field of Research
Cancer
Purity
98.04
Solubility
H2O : 4.17 mg/mL (ultrasonic)
Smiles
O[C@H]1[C@H](O)[C@@H](COP(O)(O)=O)O[C@H]1N2C(N=C(N)C=C2)=O
Molecular Formula
C9H14N3O8P
Molecular Weight
323.20
Precautions
P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501
References & Citations
[1]Momparler RL, et al. Mammalian deoxynucleoside kinase. I. Deoxycytidine kinase: purification, properties, and kinetic studies with cytosine arabinoside. J Biol Chem. 1968 Aug 25;243 (16) :4298-304.|[2]Huang S, et al. Development and application of a rapid and sensitive liquid chromatography-mass spectrometry method for simultaneous analysis of cytarabine, cytarabine monophosphate, cytarabine diphosphate and cytarabine triphosphate in the cytosol and nucleus. J Pharm Biomed Anal. 2022 Mar 20;211:114582.|[3]Perrino FW, et al. Incorporation of cytosine arabinoside monophosphate into DNA at internucleotide linkages by human DNA polymerase alpha. J Biol Chem. 1992 Nov 15;267 (32) :23043-51.|[4]McIntosh EM, et al. Inhibition of DNA replication in Saccharomyces cerevisiae by araCMP. Curr Genet. 1986;10 (8) :579-85. |[5]Schrecker AW, et al. Antitumor effect and mode of action of 1-beta-D-arabinofuranosylcytosine 5'-phosphate in leukemia L1210. Cancer Res. 1968 Apr;28 (4) :802-3.
Shipping Conditions
Blue Ice
Storage Conditions
-20°C (Powder, stored under nitrogen)
Scientific Category
Reference compound1
Clinical Information
No Development Reported

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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