M9886
2′-O-Methyladenosine
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About This Item
Empirical Formula (Hill Notation):
C11H15N5O4
CAS Number:
Molecular Weight:
281.27
UNSPSC Code:
41106305
PubChem Substance ID:
MDL number:
InChI
1S/C11H15N5O4/c1-19-8-7(18)5(2-17)20-11(8)16-4-15-6-9(12)13-3-14-10(6)16/h3-5,7-8,11,17-18H,2H2,1H3,(H2,12,13,14)
SMILES string
COC1C(O)C(CO)OC1n2cnc3c(N)ncnc23
InChI key
FPUGCISOLXNPPC-UHFFFAOYSA-N
form
solid
storage temp.
−20°C
Storage Class
13 - Non Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Regulatory Information
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Increased excretion of modified adenine nucleosides by children with adenosine deaminase deficiency.
R Hirschhorn et al.
Pediatric research, 16(5), 362-369 (1982-05-01)
We have identified seven adenine nucleosides in urines of untreated adenosine deaminase (ADA) deficient patients, four of which (adenosine, 2'-deoxyadenosine, 1-methyladenosine and N6-methyladenosine) have been previously identified in urines of normals and/or ADA deficient patients. We confirm that ADA deficient
Scott J Hecker et al.
Journal of medicinal chemistry, 50(16), 3891-3896 (2007-07-20)
2'-C-Methyladenosine exhibits impressive inhibitory activity in the cell-based hepatitis C virus (HCV) subgenomic replicon assay, by virtue of intracellular conversion to the corresponding nucleoside triphosphate (NTP) and inhibition of NS5B RNA-dependent RNA polymerase (RdRp). However, rapid degradation by adenosine deaminase
N Sofikitis et al.
Archives of andrology, 30(2), 87-92 (1993-03-01)
To determine whether the adenylate cyclase and the protein kinase C pathways act independently to modulate the human sperm acrosome reaction, we studied the effects of 2'-O-methyladenosine (adenylate cyclase inhibitor) on acrosome reactions induced by protein kinase C activators (phorbol
T Yamada et al.
Cellular and molecular life sciences : CMLS, 54(2), 125-128 (1998-04-16)
2'-O-Methylinosine (1) has been isolated for the first time and shown to be an intrinsic hypotensive principle. Its probable in vivo precursor, 2'-O-methyladenosine (3), showed stronger and even orally potent hypotensive activity. Resistance of the methyladenosine (3) against adenosine deaminase
A Theibert et al.
Developmental biology, 106(1), 166-173 (1984-11-01)
In developmentally competent Dictyostelium discoideum amoebae, binding of cAMP to high-affinity surface receptors produces a rapid activation of adenylate cyclase which adapts within minutes. The result is a transient increase in intracellular cAMP which is rapidly secreted. Adenosine inhibited this
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