Showing metabocard for Deoxyadenosine monophosphate (BMDB0000905)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 22:38:24 UTC
Update Date2020-05-21 16:27:08 UTC
BMDB IDBMDB0000905
Secondary Accession Numbers
  • BMDB00905
Metabolite Identification
Common NameDeoxyadenosine monophosphate
DescriptionDeoxyadenosine monophosphate, also known as deoxyadenylic acid or 2'-dAMP, 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. Deoxyadenosine monophosphate is a strong basic compound (based on its pKa). Deoxyadenosine monophosphate exists in all living species, ranging from bacteria to humans.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2'-dAMPChEBI
2'-Deoxy-5'-adenosine monophosphateChEBI
2'-Deoxy-AMPChEBI
2'-Deoxyadenosine 5'-(dihydrogen phosphate)ChEBI
2'-Deoxyadenosine 5'-phosphateChEBI
2'-Deoxyadenosine monophosphateChEBI
2'-DEOXYADENOSINE-5'-monophosphATEChEBI
2'-Deoxyadenylic acidChEBI
dAMPChEBI
Deoxy-5'-adenylic acidChEBI
Deoxy-AMPChEBI
Deoxyadenosine 5'-monophosphateChEBI
Deoxyadenosine 5'-phosphateChEBI
Deoxyadenylic acidChEBI
2'-Deoxyadenosine 5'-monophosphateKegg
2'-Deoxy-5'-adenosine monophosphoric acidGenerator
2'-Deoxyadenosine 5'-(dihydrogen phosphoric acid)Generator
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
DeoxyadenylateGenerator
2'-Deoxyadenosine 5'-monophosphoric acidGenerator
Deoxyadenosine monophosphoric acidGenerator
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
2'-Deoxy-5'-adenosine monophosphate, ammonium saltHMDB
2'-Deoxy-5'-adenosine monophosphate, disodium saltHMDB
2'Deoxy-5'-AMPHMDB
dAMP CPDHMDB
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 KeyKHWCHTKSEGGWEX-RRKCRQDMSA-N
Chemical Taxonomy
Description 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
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Monoalkyl phosphate
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Pyrimidine
  • Imidolactam
  • Alkyl phosphate
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Secondary alcohol
  • Azacycle
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Organic nitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Lysosome
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point148 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.4ALOGPS
logP-3.8ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.23ChemAxon
pKa (Strongest Basic)3.94ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area165.84 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity72.56 m³·mol⁻¹ChemAxon
Polarizability28.98 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Lysosome
  • Mitochondria
Biospecimen Locations
  • Liver
  • Mammary Gland
  • Spleen
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
SpleenExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000905
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022311
KNApSAcK IDNot Available
Chemspider ID12079
KEGG Compound IDC00360
BioCyc IDDAMP
BiGG ID34735
Wikipedia LinkDeoxyadenosine_monophosphate
METLIN ID3461
PubChem Compound12599
PDB IDNot Available
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)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Cytosolic purine 5'-nucleotidase
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:
O46411
Molecular weight:
64841.0
Reactions
Deoxyadenosine monophosphate + Water → Deoxyadenosine + Hydrogen phosphatedetails