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Record Information
StatusExpected but not Quantified
Creation Date2012-10-30 10:32:48 UTC
Update Date2017-12-07 15:38:14 UTC
Secondary Accession Numbers
  • HMDB59594
Metabolite Identification
Common Name2-hydroxy-dAMP
Description2-hydroxy-damp, also known as 2'-deoxyisoguanosine monophosphate or 2-oh-damp, is a member of the class of compounds known as purine 2'-deoxyribonucleoside monophosphates. Purine 2'-deoxyribonucleoside monophosphates are purine nucleotides with monophosphate group linked to the ribose moiety lacking a hydroxyl group at position 2. 2-hydroxy-damp is slightly soluble (in water) and a moderately acidic compound (based on its pKa). 2-hydroxy-damp is a substrate for: 7,8-dihydro-8-oxoguanine triphosphatase..
2'-Deoxy-2-hydroxyadenosine 5'-(dihydrogen phosphate)ChEBI
2'-Deoxyisoguanosine monophosphateChEBI
2'-Deoxy-2-hydroxyadenosine 5'-(dihydrogen phosphoric acid)Generator
2'-Deoxyisoguanosine monophosphoric acidGenerator
Chemical FormulaC10H14N5O7P
Average Molecular Weight347.2212
Monoisotopic Molecular Weight347.063084339
IUPAC Name{[(2R,3S,5R)-5-(6-amino-2-hydroxy-9H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid
Traditional Name[(2R,3S,5R)-5-(6-amino-2-hydroxypurin-9-yl)-3-hydroxyoxolan-2-yl]methoxyphosphonic acid
CAS Registry NumberNot Available
InChI Identifier
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
  • Purine 2'-deoxyribonucleoside monophosphate
  • 6-aminopurine
  • Purinone
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Pyrimidone
  • Monoalkyl phosphate
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Pyrimidine
  • Alkyl phosphate
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Azole
  • Imidazole
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Azacycle
  • Organic oxygen compound
  • Organonitrogen compound
  • Alcohol
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organooxygen compound
  • Amine
  • Primary amine
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
  • purine 2'-deoxyribonucleoside 5'-monophosphate (CHEBI:63211 )
Not Available
Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility2.91 g/LALOGPS
pKa (Strongest Acidic)1.07ChemAxon
pKa (Strongest Basic)1.72ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area186.07 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity74.48 m³·mol⁻¹ChemAxon
Polarizability29.67 ųChemAxon
Number of Rings3ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9311000000-d3a733f71ea510402177View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01ot-8922400000-06c1f8038d2ded04d525View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0901000000-df1333834dbc263fe3f3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-f1177603229cfc26bfe5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0900000000-172318ac6d54fe3338d1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002b-5109000000-4d29a72b499ff32dc95cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9400000000-61a7c83f5835448eed50View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-07134af81f89006ad08fView in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC19970
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6323381
ChEBI ID63211
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Fujikawa K, Kamiya H, Yakushiji H, Fujii Y, Nakabeppu Y, Kasai H: The oxidized forms of dATP are substrates for the human MutT homologue, the hMTH1 protein. J Biol Chem. 1999 Jun 25;274(26):18201-5. [PubMed:10373420 ]
  2. Sakai Y, Furuichi M, Takahashi M, Mishima M, Iwai S, Shirakawa M, Nakabeppu Y: A molecular basis for the selective recognition of 2-hydroxy-dATP and 8-oxo-dGTP by human MTH1. J Biol Chem. 2002 Mar 8;277(10):8579-87. Epub 2001 Dec 27. [PubMed:11756418 ]


General function:
Involved in 8-oxo-7,8-dihydroguanosine triphosphate pyrophosphatase activity
Specific function:
Antimutagenic. Acts as a sanitizing enzyme for oxidized nucleotide pools, thus suppressing cell dysfunction and death induced by oxidative stress. Hydrolyzes 8-oxo-dGTP, 8-oxo-dATP and 2-OH-dATP, thus preventing misincorporation of oxidized purine nucleoside triphosphates into DNA and subsequently preventing A:T to C:G and G:C to T:A transversions. Able to hydrolyze also the corresponding ribonucleotides, 2-OH-ATP, 8-oxo-GTP and 8-oxo-ATP.
Gene Name:
Uniprot ID:
Molecular weight:
2-hydroxy-dATP + Water → 2-hydroxy-dAMP + Pyrophosphatedetails