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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-10-30 10:32:48 UTC
Update Date2022-03-07 03:17:33 UTC
HMDB IDHMDB0059593
Secondary Accession Numbers
  • HMDB59593
Metabolite Identification
Common Name2-hydroxy-dATP
Description2-hydroxy-dATP, also known as 2-HO-dATP or D(isogtp), belongs to the class of organic compounds known as purine 2'-deoxyribonucleoside triphosphates. These are purine nucleotides with triphosphate group linked to the ribose moiety lacking a hydroxyl group at position 2. 2-hydroxy-dATP is a moderately basic compound (based on its pKa). A purine 2'-deoxyribonucleoside 5'-triphosphate in which the 2'-deoxyribonucleoside moiety is 2'-deoxy-2-hydroxyadenosine.
Structure
Thumb
Synonyms
ValueSource
2'-Deoxy-2-hydroxyadenosine 5'-(tetrahydrogen triphosphate)ChEBI
2'-Deoxy-2-hydroxyadenosine triphosphateChEBI
2'-Deoxyisoguanosine triphosphateChEBI
2-HO-dATPChEBI
2-OH-dATPChEBI
D(IsoGTP)ChEBI
2-Hydroxy-2'-deoxyadenosine 5'-triphosphateKegg
2'-Deoxy-2-hydroxyadenosine 5'-(tetrahydrogen triphosphoric acid)Generator
2'-Deoxy-2-hydroxyadenosine triphosphoric acidGenerator
2'-Deoxyisoguanosine triphosphoric acidGenerator
2-Hydroxy-2'-deoxyadenosine 5'-triphosphoric acidGenerator
2-Hydroxydeoxyadenosine triphosphateHMDB
Chemical FormulaC10H16N5O13P3
Average Molecular Weight507.181
Monoisotopic Molecular Weight506.995745159
IUPAC Name({[({[(2R,3S,5R)-5-(6-amino-2-hydroxy-9H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
Traditional Name({[(2R,3S,5R)-5-(6-amino-2-hydroxypurin-9-yl)-3-hydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxyphosphonic acid
CAS Registry NumberNot Available
SMILES
[H][C@]1(O)C[C@@]([H])(O[C@]1([H])COP(O)(=O)OP(O)(=O)OP(O)(O)=O)N1C=NC2=C(N)N=C(O)N=C12
InChI Identifier
InChI=1S/C10H16N5O13P3/c11-8-7-9(14-10(17)13-8)15(3-12-7)6-1-4(16)5(26-6)2-25-30(21,22)28-31(23,24)27-29(18,19)20/h3-6,16H,1-2H2,(H,21,22)(H,23,24)(H2,18,19,20)(H3,11,13,14,17)/t4-,5+,6+/m0/s1
InChI KeyUOACBPRDWRDEHJ-KVQBGUIXSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as purine 2'-deoxyribonucleoside triphosphates. These are purine nucleotides with triphosphate 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 triphosphates
Alternative Parents
Substituents
  • Purine 2'-deoxyribonucleoside triphosphate
  • 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'-triphosphate (CHEBI:63208 )
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
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
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC19969
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10368940
PDB IDNot Available
ChEBI ID63208
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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