5'-Deoxyadenosine
Basic information
- CAS
4754-39-6- Standard SMILES
C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O- InChIKey
XGYIMTFOTBMPFP-KQYNXXCUSA-N- Molecular formula
- C10H13N5O3
- Average molar mass
- 251.24 g/mol
- Monoisotopic mass
- 251.10183929
Overview
5'-deoxyadenosine is a 5'-deoxyribonucleoside compound having adenosine as the nucleobase. It has a role as a mouse metabolite, an Escherichia coli metabolite and a human metabolite. It is a member of adenosines and a 5'-deoxyribonucleoside. It is functionally related to an adenosine.
Names & identifiers
- Preferred name
- 5'-Deoxyadenosine
- IUPAC
- (2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-5-methyloxolane-3,4-diol
- English name
- 5'-DEOXYADENOSINE
- Molecular formula
- C10H13N5O3
- Molecular weight
- 251.24
Names & synonyms
5'-deoxyadenosine4754-39-6ADENOSINE, 5'-DEOXY-2U0TYC8Y5ACHEBI:17319(2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-5-methyloxolane-3,4-diolDTXSID901036031(2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-methyloxolane-3,4-diol5'-DAdo nucleosideRefChem:100792DTXCID301520258(2R,3R,4S,5R)-2-(6-Amino-9H-purin-9-yl)-5-methyltetrahydrofuran-3,4-diol
Show more names
5′-dAdo5’-deoxy-adenosin5''-DEOXYADENOSINE, 10 mM in DMSO2'-Deoxycytidine Monohydrate(2'-dC ? H?O)9-(5-Deoxy-β-D-ribofuranosyl)-9H-purine-6-amine6-Amino-9-(5-deoxy-β-D-ribofuranosyl)-9H-purine
5 inverted exclamation marka-Deoxyadenosine5AD(2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-5-methyl-tetrahydrofuran-3,4-diol5'-dAdo5?-Deoxyadenosine5'-deoxy-adenosineCH3Ado5''-Deoxyadenosine
Properties
Computed structural properties
- XLogP
- -0.6
- Topological polar surface area
- 119 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 1
- Heavy atoms
- 18
- Formal charge
- 0
- Complexity
- 320
Experimental & physicochemical properties
Melting Point213.0 - 214.5 °C
Physical DescriptionSolid
Collision Cross Section
166.8 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
154.8 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
171.99 Ų [M+Na]+ [CCS Type: DT; Method: stepped-field]
154.9 Ų [M-H]-
Physicochemical properties
- Melting point
- 210 · 210-212 °C
- Boiling point
- 595 · 595.0±60.0 °C(Predicted)
- Density
- 1.93 · 1.93±0.1 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- 30 mg/ml; · DMF: 30 mg/ml; DMF:PBS (pH 7.2) (1:4): 0.20 mg/ml; DMSO: 15 mg/ml
- form
- A crystalline solid
- pka
- 13.29 · 13.29±0.70(Predicted)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- rtecs
- AU7358650
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Pharmacology
Cellular LocationsExtracellular
Applications
Description5'-Deoxyadenosine is an oxidized nucleoside found in the urine of normal subjects. Oxidized nucleosides represent excellent biomarkers for determining the extent of damage in genetic material, which has long been of interest in understanding the mechanism of aging, neurodegenerative diseases, and carcinogenesis.
Uses5′-Deoxyadenosine has been used:as a standard in mass spectroscopyas an inhibitor for screening thymidine phosphorylase activityas a substrate in 5′-Deoxyadenosine deaminase (DadD) assay
Upstream & downstream products
Upstream raw materials
Downstream products
Additional notes
DefinitionChEBI: A 5'-deoxyribonucleoside compound having adenosine as the nucleobase.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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