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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:33 UTC
HMDB IDHMDB00905
Secondary Accession NumbersNone
Metabolite Identification
Common NameDeoxyadenosine monophosphate
DescriptionAdenosine 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
Synonyms
ValueSource
2'-dAMPChEBI
2'-Deoxy-5'-adenosine monophosphateChEBI
2'-Deoxy-AMPChEBI
2'-Deoxyadenosine 5'-(dihydrogen phosphate)ChEBI
2'-Deoxyadenosine 5'-monophosphateChEBI
2'-Deoxyadenosine 5'-phosphateChEBI
2'-Deoxyadenosine monophosphateChEBI
2'-DEOXYADENOSINE-5'-monophosphATEChEBI
2'-Deoxyadenylic acidChEBI
Deoxy-5'-adenylic acidChEBI
Deoxy-AMPChEBI
Deoxyadenosine 5'-monophosphateChEBI
Deoxyadenosine 5'-phosphateChEBI
Deoxyadenosine monophosphateChEBI
Deoxyadenylic acidChEBI
2'-Deoxy-5'-adenosine monophosphoric acidGenerator
2'-Deoxyadenosine 5'-(dihydrogen phosphoric acid)Generator
2'-Deoxyadenosine 5'-monophosphoric acidGenerator
2'-Deoxyadenosine 5'-phosphoric acidGenerator
2'-Deoxyadenosine monophosphoric acidGenerator
2'-DEOXYADENOSINE-5'-monophosphoric acidGenerator
2'-DeoxyadenylateGenerator
Deoxy-5'-adenylateGenerator
Deoxyadenosine 5'-monophosphoric acidGenerator
Deoxyadenosine 5'-phosphoric acidGenerator
Deoxyadenosine monophosphoric acidGenerator
DeoxyadenylateGenerator
2'-Deoxy-5'-adenylateHMDB
2'-Deoxy-5'-adenylic acidHMDB
2'-Deoxy-adenosine 5'-phosphorateHMDB
2'-Deoxy-adenosine 5'-phosphoric acidHMDB
2'-Deoxyadenosine-5'-phosphateHMDB
Deoxyadenosine-phosphateHMDB
PdAHMDB
Chemical FormulaC10H14N5O6P
Average Molecular Weight331.2218
Monoisotopic Molecular Weight331.068169717
IUPAC Name{[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid
Traditional NameDAMP
CAS Registry Number653-63-4
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 KeyInChIKey=KHWCHTKSEGGWEX-RRKCRQDMSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as purine 2'-deoxyribonucleoside monophosphates. These are purine nucleotides with monophosphate group linked to the ribose moiety lacking a hydroxyl group at position 2.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine deoxyribonucleotides
Direct ParentPurine 2'-deoxyribonucleoside monophosphates
Alternative Parents
Substituents
  • Purine 2'-deoxyribonucleoside monophosphate
  • 6-aminopurine
  • Purine
  • Imidazopyrimidine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Imidolactam
  • Alkyl phosphate
  • Pyrimidine
  • Primary aromatic amine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-substituted imidazole
  • Saccharide
  • Heteroaromatic compound
  • Oxolane
  • Imidazole
  • Azole
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Lysosome
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point148 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.71 mg/mLALOGPS
logP-2.4ALOGPS
logP-3.9ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.23ChemAxon
pKa (Strongest Basic)4.98ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area165.84 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity72.56 m3·mol-1ChemAxon
Polarizability28.98 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (6 TMS)splash10-001i-9210000000-52089369f69d88f5ea1cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0089-4096000000-d903c4b1613b2ac5f708View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9010000000-c50cec0a2ca71d42d524View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9300000000-8ebf385d33982fcaef9fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-001i-0209000000-05ded3b31c4db3d6c016View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-0019-1907000000-50567fa8c2638c9e2b6fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-003r-9804000000-9196bd87057cc65827a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Lysosome
Biofluid LocationsNot Available
Tissue Location
  • Liver
  • Spleen
Pathways
NameSMPDB LinkKEGG Link
Adenine phosphoribosyltransferase deficiency (APRT)SMP00535Not Available
Adenosine Deaminase DeficiencySMP00144Not Available
Adenylosuccinate Lyase DeficiencySMP00167Not Available
AICA-RibosiduriaSMP00168Not Available
Azathioprine PathwaySMP00427Not Available
Gout or Kelley-Seegmiller SyndromeSMP00365Not Available
Lesch-Nyhan Syndrome (LNS)SMP00364Not Available
Mercaptopurine PathwaySMP00428Not Available
Mitochondrial DNA depletion syndromeSMP00536Not Available
Molybdenum Cofactor DeficiencySMP00203Not Available
Myoadenylate deaminase deficiencySMP00537Not Available
Purine MetabolismSMP00050map00230
Purine Nucleoside Phosphorylase DeficiencySMP00210Not Available
Thioguanine PathwaySMP00430Not Available
Xanthine Dehydrogenase Deficiency (Xanthinuria)SMP00220Not Available
Xanthinuria type ISMP00512Not Available
Xanthinuria type IISMP00513Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022311
KNApSAcK IDNot Available
Chemspider ID12079
KEGG Compound IDC00360
BioCyc IDDAMP
BiGG ID34735
Wikipedia LinkDeoxyadenosine monophosphate
NuGOwiki LinkHMDB00905
Metagene LinkHMDB00905
METLIN ID3461
PubChem Compound12599
PDB IDD5M
ChEBI ID17713
References
Synthesis ReferenceScarano, 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. 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. [9217261 ]
  2. 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. [11891323 ]
  3. 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. [9862971 ]
  4. 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. [15339437 ]
  5. 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. [12376299 ]
  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. [15531653 ]
  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. [15644152 ]
  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. [10945616 ]

Enzymes

General function:
Involved in hydrolase activity
Specific function:
Hydrolyzes extracellular nucleotides into membrane permeable nucleosides.
Gene Name:
NT5E
Uniprot ID:
P21589
Molecular weight:
57948.125
Reactions
Deoxyadenosine monophosphate + Water → Deoxyadenosine + Phosphoric aciddetails
General function:
Involved in nucleotide binding
Specific function:
Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides. Helps to regulate adenosine levels (By similarity).
Gene Name:
NT5C1B
Uniprot ID:
Q96P26
Molecular weight:
68803.055
Reactions
Deoxyadenosine monophosphate + Water → Deoxyadenosine + Phosphoric aciddetails
General function:
Involved in nucleotide binding
Specific function:
Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides and has a broad substrate specificity. Helps to regulate adenosine levels in heart during ischemia and hypoxia.
Gene Name:
NT5C1A
Uniprot ID:
Q9BXI3
Molecular weight:
41020.145
Reactions
Deoxyadenosine monophosphate + Water → Deoxyadenosine + Phosphoric aciddetails
General function:
Involved in metal ion binding
Specific function:
Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides, with a preference for dUMP and dTMP, intermediate activity towards dGMP, and low activity towards dCMP and dAMP.
Gene Name:
NT5C
Uniprot ID:
Q8TCD5
Molecular weight:
Not Available
Reactions
Deoxyadenosine monophosphate + Water → Deoxyadenosine + Phosphoric aciddetails
General function:
Involved in phosphatase activity
Specific function:
Dephosphorylates specifically the 5' and 2'(3')-phosphates of uracil and thymine deoxyribonucleotides, and so protects mitochondrial DNA replication from excess dTTP. Has only marginal activity towards dIMP and dGMP.
Gene Name:
NT5M
Uniprot ID:
Q9NPB1
Molecular weight:
Not Available
Reactions
Deoxyadenosine monophosphate + Water → Deoxyadenosine + Phosphoric aciddetails
General function:
Involved in ATP binding
Specific function:
Catalyzes the reversible transfer of the terminal phosphate group between ATP and AMP. Small ubiquitous enzyme involved in energy metabolism and nucleotide synthesis that is essential for maintenance and cell growth.
Gene Name:
AK1
Uniprot ID:
P00568
Molecular weight:
21634.725
Reactions
Adenosine triphosphate + Deoxyadenosine monophosphate → ADP + dADPdetails
General function:
Involved in ATP binding
Specific function:
Catalyzes the reversible transfer of the terminal phosphate group between ATP and AMP. May also be active with GTP (By similarity).
Gene Name:
AK4
Uniprot ID:
P27144
Molecular weight:
25267.83
Reactions
Adenosine triphosphate + Deoxyadenosine monophosphate → ADP + dADPdetails
General function:
Involved in ATP binding
Specific function:
Adenylate kinase involved in maintaining ciliary structure and function (By similarity). Has highest activity toward AMP, and weaker activity toward dAMP, CMP and dCMP.
Gene Name:
AK7
Uniprot ID:
Q96M32
Molecular weight:
82657.68
Reactions
Adenosine triphosphate + Deoxyadenosine monophosphate → ADP + dADPdetails
General function:
Involved in ATP binding
Specific function:
Active on AMP and dAMP with ATP as a donor. When GTP is used as phosphate donor, the enzyme phosphorylates AMP, CMP, and to a small extent dCMP.
Gene Name:
AK5
Uniprot ID:
Q9Y6K8
Molecular weight:
60313.985
Reactions
Adenosine triphosphate + Deoxyadenosine monophosphate → ADP + dADPdetails
General function:
Involved in magnesium ion binding
Specific function:
Can act both as nucleotidase and as phosphotransferase.
Gene Name:
NT5C3
Uniprot ID:
Q9H0P0
Molecular weight:
33914.91
Reactions
Deoxyadenosine monophosphate + Water → Deoxyadenosine + Phosphoric aciddetails
General function:
Involved in 5'-nucleotidase activity
Specific function:
May have a critical role in the maintenance of a constant composition of intracellular purine/pyrimidine nucleotides in cooperation with other nucleotidases. Preferentially hydrolyzes inosine 5'-monophosphate (IMP) and other purine nucleotides.
Gene Name:
NT5C2
Uniprot ID:
P49902
Molecular weight:
64969.2
Reactions
Deoxyadenosine monophosphate + Water → Deoxyadenosine + Phosphoric aciddetails
General function:
Involved in ATP binding
Specific function:
Catalyzes the reversible transfer of the terminal phosphate group between ATP and AMP. This small ubiquitous enzyme involved in energy metabolism and nucleotide synthesis that is essential for maintenance and cell growth. Plays a key role in hematopoiesis.
Gene Name:
AK2
Uniprot ID:
P54819
Molecular weight:
24648.125
Reactions
Adenosine triphosphate + Deoxyadenosine monophosphate → ADP + dADPdetails