dAMP
Basic information
- CAS
653-63-4- Standard SMILES
Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)O)O1- InChIKey
KHWCHTKSEGGWEX-RRKCRQDMSA-N- Molecular formula
- C10H14N5O6P
- Average molar mass
- 331.22 g/mol
- Monoisotopic mass
- 331.06817018
Overview
2'-deoxyadenosine 5'-monophosphate is a purine 2'-deoxyribonucleoside 5'-monophosphate having adenine as the nucleobase. It has a role as a fundamental metabolite. It is a 2'-deoxyadenosine 5'-phosphate and a purine 2'-deoxyribonucleoside 5'-monophosphate. It is a conjugate acid of a 2'-deoxyadenosine 5'-monophosphate(2-).
Names & identifiers
- Preferred name
- dAMP
- IUPAC
- [(2R,3S,5R)-5-(6-aminopurin-9-yl)-3-hydroxyoxolan-2-yl]methyl dihydrogen phosphate
- English name
- 2'-Deoxyadenosine 5'-phosphate
- Molecular formula
- C10H14N5O6P
- Molecular weight
- 331.22
Names & synonyms
653-63-4dAMP2'-Deoxyadenosine 5'-monophosphate5'-Adenylic acid, 2'-deoxy-Deoxyadenylic acidDeoxy-AMP2'-Deoxy-AMPDeoxyadenosine 5'-monophosphate2'-dAMPDeoxyadenosine 5'-phosphate2'-Deoxyadenosine monophosphate2'-Deoxy-5'-adenosine monophosphate
Show more names
2'-Deoxyadenosine-5'-monophosphateD-AMP5'-dAMPdAMP.H25'-dAMP.H22'-Deoxy-5'-AMP2'-DEOXYADENYLIC ACID
DeoxyadenylateVFR8I97ORMDTXSID901034859CHEBI:17713NSC-77680NSC-82625dAMP cpd2'deoxy-5'-AMP
Database identifiers
- CAS
653-63-4- PubChem CID
- 12599
- DTXSID
DTXSID901034859- ChEMBL
CHEMBL1206239
Properties
Computed structural properties
- XLogP
- -2.2
- Topological polar surface area
- 166 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 10
- Rotatable bonds
- 4
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 452
Experimental & physicochemical properties
SpringerMaterials PropertiesAngular frequency
Melting Point148 °C
Physical DescriptionSolid
Collision Cross Section
168.1 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
164 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine]
173 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
176.68 Ų [M+Na]+ [CCS Type: DT; Method: stepped-field]
173.9 Ų [M+Na]+
Physicochemical properties
- Melting point
- 148 °C · 148 °C
- Boiling point
- 753.5 · 753.5±70.0 °C(Predicted)
- Density
- 2.17 · 2.17
- storage temp.
- -20 °C · -20°C
- solubility
- DMSO (Slightly)
- pka
- 1.86 · 1.86±0.10(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.
GHS classification
GHS ClassificationNot Classified
Hazard information
Hazard Classes and CategoriesNot Classified
Safety data
- wgk
- 3
- hs_code
- 29349990
- risk_code
- 20/21/22-36/37/38
- hazard_code
- Xn,Xi
- safety_code
- 26-36-37/39-24/25
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Pharmacology
Tissue LocationsLiver
Cellular LocationsLysosome
Metabolite PathwaysAdenine phosphoribosyltransferase deficiency (APRT)
Applications
Description2’-Deoxyadenosine-5''-monophosphate is a derivative of the nucleic acid, AMP, in which the hydroxyl group on the 2'' carbon of the pentose has been reduced to a hydrogen atom. It has been used in the synthesis of novel photoaffinity labels for incorporation into DNA and to study adenosine-based interactions during DNA synthesis and DNA damage.
Uses2’-Deoxyadenosine 5’Monophosphate is the first nucleotide of the phi 29 DNA.
Upstream & downstream products
Upstream raw materials
Additional notes
ChEBI: 2'-deoxyadenosine 5'-monophosphate is a purine 2'-deoxyribonucleoside 5'-monophosphate having adenine as the nucleobase. It has a role as a fundamental metabolite. It is a purine 2'-deoxyribonucleoside 5'-monophosphate and a 2'-deoxyadenosine 5'-phosphate. It is a conjugate acid of a 2'-deoxyadenosine 5'-monophosphate(2-).
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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