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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-10-30 10:32:48 UTC
Update Date2017-12-07 15:38:14 UTC
HMDB IDHMDB0059594
Secondary Accession Numbers
  • HMDB59594
Metabolite Identification
Common Name2-hydroxy-dAMP
Description2-hydroxy-damp is a substrate for: 7,8-dihydro-8-oxoguanine triphosphatase.
Structure
Thumb
Synonyms
ValueSource
2'-Deoxy-2-hydroxyadenosine 5'-(dihydrogen phosphate)ChEBI
2'-Deoxyisoguanosine monophosphateChEBI
2-HO-dAMPChEBI
2-OH-dAMPChEBI
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
SMILES
[H][C@]1(O)C[C@@]([H])(O[C@]1([H])COP(O)(O)=O)N1C=NC2=C(N)N=C(O)N=C12
InChI Identifier
InChI=1S/C10H14N5O7P/c11-8-7-9(14-10(17)13-8)15(3-12-7)6-1-4(16)5(22-6)2-21-23(18,19)20/h3-6,16H,1-2H2,(H2,18,19,20)(H3,11,13,14,17)/t4-,5+,6+/m0/s1
InChI KeyGEQDRKVFKBSPSW-KVQBGUIXSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassNucleosides, nucleotides, and analogues
Sub ClassPurine nucleotides
Direct ParentPurine 2'-deoxyribonucleoside monophosphates
Alternative Parents
Substituents
  • Purine 2'-deoxyribonucleoside monophosphate
  • 6-aminopurine
  • Purinone
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Pyrimidone
  • Monoalkyl phosphate
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Primary aromatic amine
  • Pyrimidine
  • Alkyl phosphate
  • Heteroaromatic compound
  • Azole
  • Tetrahydrofuran
  • Imidazole
  • Secondary alcohol
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Alcohol
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organooxygen compound
  • Amine
  • Primary amine
  • Organic oxygen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
  • purine 2'-deoxyribonucleoside 5'-monophosphate (CHEBI:63211 )
Ontology
Not Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.91 g/LALOGPS
logP-1.5ALOGPS
logP-3ChemAxon
logS-2.1ALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
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
NameSMPDB/PathwhizKEGG
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 IDNot Available
KNApSAcK IDNot Available
Chemspider ID4883392
KEGG Compound IDC19970
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6323381
PDB IDNot Available
ChEBI ID63211
References
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 ]

Enzymes

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:
NUDT1
Uniprot ID:
P36639
Molecular weight:
17951.435
Reactions
2-hydroxy-dATP + Water → 2-hydroxy-dAMP + Pyrophosphatedetails