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Merck
CN

C6760

Cytosine β-D-arabinofuranoside 5′-monophosphate

≥99%

Synonym(s):

Ara-CMP

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About This Item

Empirical Formula (Hill Notation):
C9H14N3O8P
CAS Number:
Molecular Weight:
323.20
UNSPSC Code:
41106305
PubChem Substance ID:
MDL number:
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assay

≥99%

form

solid

storage temp.

−20°C

SMILES string

NC1=NC(=O)N(C=C1)[C@@H]2O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]2O

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

InChI key

IERHLVCPSMICTF-CCXZUQQUSA-N



pictograms

Health hazard

signalword

Warning

hcodes

pcodes

Hazard Classifications

Carc. 2

Storage Class

13 - Non Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

Regulatory Information

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E M McIntosh et al.
Current genetics, 10(8), 579-585 (1986-01-01)
Cytosine arabinoside (araC), a potent inhibitor of DNA replication in mammalian cells, was found to be completely ineffective in Saccharomyces cerevisiae. The 5' monophosphate derivative, araCMP, is toxic and effectively inhibits both nuclear and mitochondrial DNA synthesis in this organism.
D D Ross et al.
Cancer research, 50(9), 2658-2666 (1990-05-01)
The pH-step alkaline elution method enables the isolation and quantification of nascent DNA (nDNA) replication intermediates, including Okazaki fragments, short length nDNA from replicon origins, longer lengths of nascent but subgenomic length nDNA (molecular weight, 20-30 x 10(6)), and full
F W Perrino et al.
The Journal of biological chemistry, 267(32), 23043-23051 (1992-11-15)
The incorporation of cytosine arabinoside monophosphate (araCMP) into DNA at internucleotide linkages by DNA polymerase alpha (DNA pol alpha) has been investigated by using oligonucleotide primed DNA templates. The products of reactions catalyzed by DNA pol alpha in vitro were