You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2012-10-30 10:32:48 UTC
Update Date2016-02-11 07:48:54 UTC
HMDB IDHMDB59594
Secondary Accession NumbersNone
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 KeyInChIKey=GEQDRKVFKBSPSW-KVQBGUIXSA-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
  • Purinone
  • 6-aminopurine
  • Purine
  • Imidazopyrimidine
  • Monoalkyl phosphate
  • Pyrimidone
  • 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
  • purine 2'-deoxyribonucleoside 5'-monophosphate (CHEBI:63211 )
Ontology
StatusExpected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot 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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity74.48 m3·mol-1ChemAxon
Polarizability29.67 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
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
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
NuGOwiki LinkHMDB59594
Metagene LinkHMDB59594
METLIN IDNot Available
PubChem Compound6323381
PDB IDNot Available
ChEBI ID63211
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

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