D7400
2′-Deoxyadenosine monohydrate
≥99%, synthetic (organic), powder
Synonym(s):
9-(2-Deoxy-β-D-ribofuranosyl)adenine, Adenine deoxyriboside
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About This Item
Empirical Formula (Hill Notation):
C10H13N5O3 · H2O
CAS Number:
Molecular Weight:
269.26
NACRES:
NA.51
PubChem Substance ID:
UNSPSC Code:
41106305
EC Number:
213-488-7
MDL number:
Beilstein/REAXYS Number:
91015
Assay:
≥99%
Biological source:
synthetic (organic)
Form:
powder
Solubility:
water: 25 mg/mL, clear to slightly hazy, colorless to faintly yellow
Storage temp.:
2-8°C
Product Name
2′-Deoxyadenosine monohydrate, ≥99%
biological source
synthetic (organic)
Quality Level
assay
≥99%
form
powder
solubility
water: 25 mg/mL, clear to slightly hazy, colorless to faintly yellow
storage temp.
2-8°C
SMILES string
[H]O[H].Nc1ncnc2n(cnc12)[C@H]3C[C@H](O)[C@@H](CO)O3
InChI
1S/C10H13N5O3/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(17)6(2-16)18-7/h3-7,16-17H,1-2H2,(H2,11,12,13)/t5-,6+,7+/m0/s1
InChI key
OLXZPDWKRNYJJZ-RRKCRQDMSA-N
Application
2′-Deoxyadenosine monohydrate has been used:
- as a component for nucleoside supplementation
- as a standard for to estimate DNA global methylation rate in proliferating oil palm embryogenic suspensions
- to reverse sterile alpha motif (SAM) and histidine-aspartate (HD) domain-containing protein (SAMHD1)
- inhibition of human immunodeficiency virus (HIV-1) and hepatitis B virus (HBV)
Biochem/physiol Actions
2′-Deoxyadenosine (2′-dAdo), a deoxyribonucleoside, may be used by some cells as an energy source under energy stress conditions and to affect cAMP levels. 2′-dAdo is used in comparison studies of the functions of adenosine analogues on various biological processes.
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Storage Class
11 - Combustible Solids
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Faceshields, Gloves
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M Nakamura et al.
The Journal of biological chemistry, 257(23), 13945-13950 (1982-12-10)
Regulation of glucose metabolism in glycolysis by round spermatids was studied. Assay of activities of 11 glycolytic enzymes in cell-free spermatid extracts showed that hexokinase, phosphofructokinase, and glyceraldehyde-3-phosphate dehydrogenase had the lowest activities. When the cells were incubated with glucose
O Magnus et al.
International journal of fertility, 38(2), 123-128 (1993-03-01)
To find differences in effect on sperm motility of agents that increase intracellular cAMP: manganese ion, methyl-isobutyl-xanthine (MIX), 2-deoxyadenosine, glucose, and Mn-MIX and Mn-glucose. Nine men with asthenozoospermia vs. fertile donors. Sperm was washed in Hepes-buffered saline, motility tested by
Michela Giannecchini et al.
The international journal of biochemistry & cell biology, 37(4), 797-808 (2005-02-08)
In this paper, we report that cells undergoing metabolic stress conditions may use the ribose moiety of nucleosides as energy source to slow down cellular damage. In fact, the phosphorolytic cleavage of the N-glycosidic bond of nucleosides generates, without energy