| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2005-11-16 08:48:42 -0700 |
| Update Date |
2013-02-08 17:09:33 -0700 |
| HMDB ID |
HMDB00905 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
|---|
| Common Name |
Deoxyadenosine monophosphate |
| Description |
Adenosine is a nucleoside comprised of adenine attached to a ribose (ribofuranose) moiety via a -N9-glycosidic bond. Deoxyadenosine monophosphate is a derivative of the common nucleic acid ATP, or adenosine triphosphate, in which the -OH (hydroxyl) group on the 2' carbon on the nucleotide's pentose has been removed (hence the deoxy- part of the name). Additionally, the monophosphate of the name indicates that two of the phosphoryl groups of GTP have been removed, most likely by hydrolysis. Deoxyadenosine monophosphate is abbreviated dAMP. (Wikipedia). |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- 2'-dAMP
- 2'-Deoxy-5'-adenylate
- 2'-Deoxy-5'-adenylic acid
- 2'-Deoxy-Adenosine 5'-phosphorate
- 2'-Deoxy-Adenosine 5'-phosphoric acid
- 2'-Deoxy-AMP
- 2'-Deoxyadenosine 5'-monophosphate
- 2'-Deoxyadenosine 5'-phosphate
- 2'-Deoxyadenosine monophosphate
- 2'-Deoxyadenosine-5'-monophosphate
- 2'-Deoxyadenosine-5'-phosphate
- 2'-Deoxyadenylate
- 2'-Deoxyadenylic acid
- dAMP
- Deoxy-5'-adenylate
- Deoxy-5'-adenylic acid
- Deoxy-AMP
- Deoxyadenosine 5'-monophosphate
- Deoxyadenosine 5'-phosphate
- Deoxyadenosine monophosphate
- Deoxyadenosine-phosphate
- Deoxyadenylate
- Deoxyadenylic acid
- PdA
|
| Chemical Formula |
C10H14N5O6P |
| Average Molecular Weight |
331.2218 |
| Monoisotopic Molecular Weight |
331.068169717 |
| IUPAC Name |
{[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid |
| Traditional IUPAC Name |
[(2R,3S,5R)-5-(6-aminopurin-9-yl)-3-hydroxyoxolan-2-yl]methoxyphosphonic acid |
| CAS Registry Number |
653-63-4 |
| SMILES |
NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](COP(O)(O)=O)O1 |
| InChI Identifier |
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 |
| InChI Key |
KHWCHTKSEGGWEX-RRKCRQDMSA-N |
| Chemical Taxonomy |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Nucleosides, Nucleotides, and Analogues |
| Class |
Purine Nucleotides |
| Sub Class |
Purine Deoxyribonucleotides |
| Other Descriptors |
- 2'-deoxyadenosine 5'-phosphate(ChEBI)
- Aromatic Heteropolycyclic Compounds
- Deoxyribonucleotides(KEGG)
- Organic Compounds
- purine 2'-deoxyribonucleoside 5'-monophosphate(ChEBI)
|
| Substituents |
- Aminopyrimidine
- Imidazole
- Imidazopyrimidine
- Organic Hypophosphite
- Organic Phosphite
- Oxolane
- Phosphoric Acid Ester
- Purine
- Pyrimidine
- Secondary Alcohol
|
| Direct Parent |
Purine 2'-deoxyribonucleoside Monophosphates |
| Ontology |
|---|
| Status |
Expected and Not Quantified |
| Origin |
|
| Biofunction |
Not Available |
| Application |
Not Available |
| Cellular locations |
|
| Physical Properties |
|---|
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
148 °C |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
Not Available |
Not Available |
| LogP |
Not Available |
Not Available |
|
| Predicted Properties |
|
| Spectra |
|---|
|
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| Biological Properties |
|---|
| Cellular Locations |
|
| Biofluid Locations |
Not Available
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| Tissue Location |
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| Pathways |
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| Normal Concentrations |
|---|
|
Not Available |
| Abnormal Concentrations |
|---|
|
Not Available |
| Associated Disorders and Diseases |
|---|
| Disease References |
None |
| Associated OMIM IDs |
None |
| External Links |
|---|
| DrugBank ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB022311 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
12079  |
| KEGG Compound ID |
C00360 |
| BioCyc ID |
DAMP |
| BiGG ID |
34735 |
| Wikipedia Link |
Deoxyadenosine monophosphate |
| NuGOwiki Link |
HMDB00905 |
| Metagene Link |
HMDB00905 |
| METLIN ID |
3461 |
| PubChem Compound |
12599 |
| PDB ID |
D5M |
| ChEBI ID |
17713 |
| References |
|---|
| Synthesis Reference |
Scarano, E. Incorporation of adenine-C14 into deoxyadenylic acid. Bollettino - Societa Italiana di Biologia Sperimentale (1958), 34 1620-1. |
| Material Safety Data Sheet (MSDS) |
Download (PDF)
|
| General References |
- Avkin S, Adar S, Blander G, Livneh Z: Quantitative measurement of translesion replication in human cells: evidence for bypass of abasic sites by a replicative DNA polymerase. Proc Natl Acad Sci U S A. 2002 Mar 19;99(6):3764-9. Epub 2002 Mar 12.
Pubmed: 11891323
- Duarte V, Muller JG, Burrows CJ: Insertion of dGMP and dAMP during in vitro DNA synthesis opposite an oxidized form of 7,8-dihydro-8-oxoguanine. Nucleic Acids Res. 1999 Jan 15;27(2):496-502.
Pubmed: 9862971
- Chen XR, Li GM, Wang JR, Chen JJ: [Portal hemodynamics in patients with different syndromes of cirrhosis] Zhong Xi Yi Jie He Xue Bao. 2004 May;2(3):178-81.
Pubmed: 15339437
- Zhong H, Zang KT: Therapeutic approaches for chronic gastralgia based on differentiation of symptoms and signs. Di Yi Jun Yi Da Xue Xue Bao. 2002 Jul;22(7):639-40.
Pubmed: 12376299
- Hohenester E, Hutchinson WL, Pepys MB, Wood SP: Crystal structure of a decameric complex of human serum amyloid P component with bound dAMP. J Mol Biol. 1997 Jun 20;269(4):570-8.
Pubmed: 9217261
- Hashimoto K, Tominaga Y, Nakabeppu Y, Moriya M: Futile short-patch DNA base excision repair of adenine:8-oxoguanine mispair. Nucleic Acids Res. 2004 Nov 5;32(19):5928-34. Print 2004.
Pubmed: 15531653
- Zhang Q, Zhang WT, Wei JJ, Wang XB, Liu P: [Combined use of factor analysis and cluster analysis in classification of traditional Chinese medical syndromes in patients with posthepatitic cirrhosis] Zhong Xi Yi Jie He Xue Bao. 2005 Jan;3(1):14-8.
Pubmed: 15644152
- Levine RL, Yang IY, Hossain M, Pandya GA, Grollman AP, Moriya M: Mutagenesis induced by a single 1,N6-ethenodeoxyadenosine adduct in human cells. Cancer Res. 2000 Aug 1;60(15):4098-104.
Pubmed: 10945616
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