Human Metabolome Database Version 3.5

Showing metabocard for Deoxyadenosine monophosphate (HMDB00905)

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 Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 2'-dAMP
  2. 2'-Deoxy-5'-adenylate
  3. 2'-Deoxy-5'-adenylic acid
  4. 2'-Deoxy-Adenosine 5'-phosphorate
  5. 2'-Deoxy-Adenosine 5'-phosphoric acid
  6. 2'-Deoxy-AMP
  7. 2'-Deoxyadenosine 5'-monophosphate
  8. 2'-Deoxyadenosine 5'-phosphate
  9. 2'-Deoxyadenosine monophosphate
  10. 2'-Deoxyadenosine-5'-monophosphate
  11. 2'-Deoxyadenosine-5'-phosphate
  12. 2'-Deoxyadenylate
  13. 2'-Deoxyadenylic acid
  14. dAMP
  15. Deoxy-5'-adenylate
  16. Deoxy-5'-adenylic acid
  17. Deoxy-AMP
  18. Deoxyadenosine 5'-monophosphate
  19. Deoxyadenosine 5'-phosphate
  20. Deoxyadenosine monophosphate
  21. Deoxyadenosine-phosphate
  22. Deoxyadenylate
  23. Deoxyadenylic acid
  24. 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
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Lysosome
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
Property Value Source
Water Solubility 2.71 g/L ALOGPS
LogP -2.44 ALOGPS
LogP -3.9 ChemAxon
LogS -2.09 ALOGPS
pKa (strongest acidic) 1.23 ChemAxon
pKa (strongest basic) 4.98 ChemAxon
Hydrogen Acceptor Count 9 ChemAxon
Hydrogen Donor Count 4 ChemAxon
Polar Surface Area 165.84 A2 ChemAxon
Rotatable Bond Count 4 ChemAxon
Refractivity 72.56 ChemAxon
Polarizability 28.98 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -2 ChemAxon
Spectra
Gas-MS Spectrum
13C NMR Spectrum
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)
MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters)
MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30
MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters)
[1H,1H] 2D NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Lysosome
Biofluid Locations Not Available
Tissue Location
  • Liver
  • Spleen
Pathways
Name SMPDB Link KEGG Link
Purine Metabolism SMP00050 map00230 Link_out
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite 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 Link_out
KEGG Compound ID C00360 Link_out
BioCyc ID DAMP Link_out
BiGG ID 34735 Link_out
Wikipedia Link Deoxyadenosine monophosphate Link_out
NuGOwiki Link HMDB00905 Link_out
Metagene Link HMDB00905 Link_out
METLIN ID 3461 Link_out
PubChem Compound 12599 Link_out
PDB ID D5M Link_out
ChEBI ID 17713 Link_out
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
  1. 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 Link_out
  2. 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 Link_out
  3. 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 Link_out
  4. 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 Link_out
  5. 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 Link_out
  6. 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 Link_out
  7. 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 Link_out
  8. 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 Link_out

Enzymes
Name: 5'-nucleotidase
Reactions:
Deoxyadenosine monophosphate + Water unknown Deoxyadenosine + Phosphoric acid details
Gene Name: NT5E
Uniprot ID: P21589 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytosolic 5'-nucleotidase 1B
Reactions:
Deoxyadenosine monophosphate + Water unknown Deoxyadenosine + Phosphoric acid details
Gene Name: NT5C1B
Uniprot ID: Q96P26 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytosolic 5'-nucleotidase 1A
Reactions:
Deoxyadenosine monophosphate + Water unknown Deoxyadenosine + Phosphoric acid details
Gene Name: NT5C1A
Uniprot ID: Q9BXI3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 5'(3')-deoxyribonucleotidase, cytosolic type
Reactions:
Deoxyadenosine monophosphate + Water unknown Deoxyadenosine + Phosphoric acid details
Gene Name: NT5C
Uniprot ID: Q8TCD5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 5'(3')-deoxyribonucleotidase, mitochondrial
Reactions:
Deoxyadenosine monophosphate + Water unknown Deoxyadenosine + Phosphoric acid details
Gene Name: NT5M
Uniprot ID: Q9NPB1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Adenylate kinase isoenzyme 1
Reactions:
Adenosine triphosphate + Deoxyadenosine monophosphate unknown ADP + dADP details
Gene Name: AK1
Uniprot ID: P00568 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Adenylate kinase isoenzyme 4, mitochondrial
Reactions:
Adenosine triphosphate + Deoxyadenosine monophosphate unknown ADP + dADP details
Gene Name: AK4
Uniprot ID: P27144 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Adenylate kinase 7
Reactions:
Adenosine triphosphate + Deoxyadenosine monophosphate unknown ADP + dADP details
Gene Name: AK7
Uniprot ID: Q96M32 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Adenylate kinase isoenzyme 5
Reactions:
Adenosine triphosphate + Deoxyadenosine monophosphate unknown ADP + dADP details
Gene Name: AK5
Uniprot ID: Q9Y6K8 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytosolic 5'-nucleotidase 3
Reactions:
Deoxyadenosine monophosphate + Water unknown Deoxyadenosine + Phosphoric acid details
Gene Name: NT5C3
Uniprot ID: Q9H0P0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytosolic purine 5'-nucleotidase
Reactions:
Deoxyadenosine monophosphate + Water unknown Deoxyadenosine + Phosphoric acid details
Gene Name: NT5C2
Uniprot ID: P49902 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Adenylate kinase 2, mitochondrial
Reactions:
Adenosine triphosphate + Deoxyadenosine monophosphate unknown ADP + dADP details
Gene Name: AK2
Uniprot ID: P54819 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA