Record Information
Version1.0
Created at2020-04-17 18:45:17 UTC
Updated at2020-11-18 16:38:54 UTC
CannabisDB IDCDB004870
Secondary Accession NumbersNot Available
Cannabis Compound 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. Within humans, deoxyadenosine monophosphate participates in a number of enzymatic reactions. In particular, deoxyadenosine monophosphate can be converted into dADP through the action of the enzyme adenylate kinase isoenzyme 1. In addition, deoxyadenosine monophosphate can be converted into deoxyadenosine; which is mediated by the enzyme cytosolic purine 5'-nucleotidase. In humans, deoxyadenosine monophosphate is involved in the metabolic disorder called the gout or kelley-seegmiller syndrome pathway. A purine 2'-deoxyribonucleoside 5'-monophosphate having adenine as the nucleobase. Deoxyadenosine monophosphate is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
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 Weight331.22
Monoisotopic Molecular Weight331.0682
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
Disposition

Source:

Biological location:

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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSDeoxyadenosine monophosphate, 6 TMS, GC-MS Spectrumsplash10-001i-9210000000-52089369f69d88f5ea1cSpectrum
GC-MSDeoxyadenosine monophosphate, non-derivatized, GC-MS Spectrumsplash10-001i-9210000000-52089369f69d88f5ea1cSpectrum
Predicted GC-MSDeoxyadenosine monophosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0005-9601000000-2ae616924ca1385b9693Spectrum
Predicted GC-MSDeoxyadenosine monophosphate, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01ow-9433000000-7d0506e58e284d44779cSpectrum
Predicted GC-MSDeoxyadenosine monophosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDeoxyadenosine monophosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDeoxyadenosine monophosphate, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDeoxyadenosine monophosphate, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDeoxyadenosine monophosphate, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDeoxyadenosine monophosphate, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDeoxyadenosine monophosphate, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0089-4096000000-d903c4b1613b2ac5f708Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9010000000-c50cec0a2ca71d42d524Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9300000000-8ebf385d33982fcaef9fSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-001i-0209000000-05ded3b31c4db3d6c016Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-0019-1907000000-50567fa8c2638c9e2b6fSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-003r-9804000000-9196bd87057cc65827a3Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-003r-9804000000-9196bd87057cc65827a3Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0209000000-05ded3b31c4db3d6c016Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0019-1907000000-50567fa8c2638c9e2b6fSpectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-000i-2900000000-7eab9e6d466f6f6fc5caSpectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0019-1907000000-50567fa8c2638c9e2b6fSpectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0019-4900000000-7e54c832e11165a43f06Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-000i-6900000000-2a484df957d9a58803cdSpectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-000i-4930000000-881e3633ecf1832b39c1Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-0921000000-913b60e77094a1a288c9Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-2900000000-ee54193845dfdd45afd8Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-000i-1900000000-700554bbc39a72147ed1Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0059-9500000000-f0950c77946a8c1b5112Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-000i-1930000000-a75e389060d82c5d0b7fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0901000000-2d08f4128523b3afc5f3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-3c531326eee979b1f9a3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900000000-e832807c09bda720138bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-6309000000-3c3e22257c611faa9f07Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9500000000-2304362c6bf7c8e4aa49Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-f628177d4207cc1a2c0bSpectrum
NMR
TypeDescriptionView
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
2D NMR[1H,1H] 2D NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
5'-nucleotidaseNT5E6q14-q21P21589 details
Cytosolic 5'-nucleotidase 1BNT5C1B2p24.2Q96P26 details
Cytosolic 5'-nucleotidase 1ANT5C1A1p34.3-p33Q9BXI3 details
5'(3')-deoxyribonucleotidase, cytosolic typeNT5CQ8TCD5 details
5'(3')-deoxyribonucleotidase, mitochondrialNT5MQ9NPB1 details
Adenylate kinase isoenzyme 1AK19q34.1P00568 details
Adenylate kinase isoenzyme 4, mitochondrialAK41p31.3P27144 details
Adenylate kinase 7AK714q32.2Q96M32 details
Adenylate kinase isoenzyme 5AK51p31Q9Y6K8 details
Cytosolic 5'-nucleotidase 3NT5C37p14.3Q9H0P0 details
Cytosolic purine 5'-nucleotidaseNT5C210q24.32P49902 details
Adenylate kinase 2, mitochondrialAK21p34P54819 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
5'-nucleotidaseNT5E6q14-q21P21589 details
Cytosolic 5'-nucleotidase 1BNT5C1B2p24.2Q96P26 details
Cytosolic 5'-nucleotidase 1ANT5C1A1p34.3-p33Q9BXI3 details
5'(3')-deoxyribonucleotidase, cytosolic typeNT5CQ8TCD5 details
5'(3')-deoxyribonucleotidase, mitochondrialNT5MQ9NPB1 details
Cytosolic 5'-nucleotidase 3NT5C37p14.3Q9H0P0 details
Cytosolic purine 5'-nucleotidaseNT5C210q24.32P49902 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0000905
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
General ReferencesNot Available

Only showing the first 10 proteins. There are 19 proteins in total.

Enzymes

General function:
Involved in hydrolase activity
Specific function:
Hydrolyzes extracellular nucleotides into membrane permeable nucleosides.
Gene Name:
NT5E
Uniprot ID:
P21589
Molecular weight:
57948.125
General function:
Involved in nucleotide binding
Specific function:
Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides. Helps to regulate adenosine levels (By similarity).
Gene Name:
NT5C1B
Uniprot ID:
Q96P26
Molecular weight:
68803.055
General function:
Involved in nucleotide binding
Specific function:
Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides and has a broad substrate specificity. Helps to regulate adenosine levels in heart during ischemia and hypoxia.
Gene Name:
NT5C1A
Uniprot ID:
Q9BXI3
Molecular weight:
41020.145
General function:
Involved in metal ion binding
Specific function:
Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides, with a preference for dUMP and dTMP, intermediate activity towards dGMP, and low activity towards dCMP and dAMP.
Gene Name:
NT5C
Uniprot ID:
Q8TCD5
Molecular weight:
Not Available
General function:
Involved in phosphatase activity
Specific function:
Dephosphorylates specifically the 5' and 2'(3')-phosphates of uracil and thymine deoxyribonucleotides, and so protects mitochondrial DNA replication from excess dTTP. Has only marginal activity towards dIMP and dGMP.
Gene Name:
NT5M
Uniprot ID:
Q9NPB1
Molecular weight:
Not Available
General function:
Involved in ATP binding
Specific function:
Catalyzes the reversible transfer of the terminal phosphate group between ATP and AMP. Small ubiquitous enzyme involved in energy metabolism and nucleotide synthesis that is essential for maintenance and cell growth.
Gene Name:
AK1
Uniprot ID:
P00568
Molecular weight:
21634.725
General function:
Involved in ATP binding
Specific function:
Catalyzes the reversible transfer of the terminal phosphate group between ATP and AMP. May also be active with GTP (By similarity).
Gene Name:
AK4
Uniprot ID:
P27144
Molecular weight:
25267.83
General function:
Involved in ATP binding
Specific function:
Adenylate kinase involved in maintaining ciliary structure and function (By similarity). Has highest activity toward AMP, and weaker activity toward dAMP, CMP and dCMP.
Gene Name:
AK7
Uniprot ID:
Q96M32
Molecular weight:
82657.68
General function:
Involved in ATP binding
Specific function:
Active on AMP and dAMP with ATP as a donor. When GTP is used as phosphate donor, the enzyme phosphorylates AMP, CMP, and to a small extent dCMP.
Gene Name:
AK5
Uniprot ID:
Q9Y6K8
Molecular weight:
60313.985
General function:
Involved in magnesium ion binding
Specific function:
Can act both as nucleotidase and as phosphotransferase.
Gene Name:
NT5C3
Uniprot ID:
Q9H0P0
Molecular weight:
33914.91

Only showing the first 10 proteins. There are 19 proteins in total.