Adenosine, 5'-phosphoric acid
Basic information
- CAS
653-63-4- Standard SMILES
Nc1ncnc2c1ncn2C1CC(O)C(COP(=O)(O)O)O1- InChIKey
KHWCHTKSEGGWEX-UHFFFAOYSA-N- Molecular formula
- C10H14N5O6P
- Average molar mass
- 331.22 g/mol
- Monoisotopic mass
- 331.06817018
Overview
Deoxyadenosine monophosphate is a metabolite found in or produced by Escherichia coli (strain K12, MG1655).
Names & identifiers
- Preferred name
- Adenosine, 5'-phosphoric acid
- IUPAC
- [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
Adenosine, 5'-phosphoric acidRefChem:1076181(5-(6-aminopurin-9-yl)-3-hydroxyoxolan-2-yl)methyl dihydrogen phosphateAdenosine, 5'-(dihydrogen phosphate)C10H14N5O6PSCHEMBL11927745HMS3370G15NSC77680NSC82625s32482'-deoxy-adenosine--5'-monophosphate[5-(6-aminopurin-9-yl)-3-hydroxy-tetrahydrofuran-2-yl]methyl dihydrogen phosphate
Show more names
2'-dAMP2'-Deoxyadenosine-5'-monophosphateD-AMP5'-dAMPdAMP.H25'-dAMP.H22'-Deoxy-AMP2'-Deoxy-5'-AMPDEOXYADENYLIC ACID2'-DEOXYADENYLIC ACID
2 inverted exclamation mark -Deoxyadenosine 5 inverted exclamation mark -monophosphatePHOSPHORIC ACID MONO-(5-(6-AMINO-PURIN-9-YL)-3-HO-4H-FURAN-2-YLMETHYL) ESTER
Database identifiers
- CAS
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
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)
- form
- Crystalline Powder
- color
- White
- biological source
- synthetic (organic)
- Water Solubility
- 1 N · Soluble in 1N ammonium hhydroxide (50 mg/ml) and water.
- Stability
- Hygroscopic
- InChI
- InChI=1S/C10H14N5O6P/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(16)6(21-7)2-20-22(17,18)19/h3-7,16H,1-2H2,(H2,11,12,13)(H2,17,18,19)/t5-,6+,7+/m0/s1
- InChIKey
- KHWCHTKSEGGWEX-RRKCRQDMSA-N
- SMILES
- P(OC[C@H]1O[C@@H](N2C3C(=C(N=CN=3)N)N=C2)C[C@@H]1O)(O)(O)=O
- CAS DataBase Reference
- 653 · 653-63-4(CAS DataBase Reference)
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
- 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
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
DefinitionChEBI: 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
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Compound notes
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