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Identification
YMDB IDYMDB00451
NamedAMP
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
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
Synonyms
  • (3-Hydroxyphenyl)dimethylamine
  • 2-deoxyadenosine 5-monophosphate
  • 2-deoxyadenosine 5-phosphate
  • 2'-dAMP
  • 2'-deoxy-5'-adenosine monophosphate
  • 2'-Deoxy-5'-adenylate
  • 2'-Deoxy-5'-adenylic acid
  • 2'-deoxy-Adenosine 5'-phosphorate
  • 2'-deoxy-Adenosine 5'-phosphoric acid
  • 2'-Deoxy-AMP
  • 2'-deoxyadenosine 5'-(dihydrogen phosphate)
  • 2'-Deoxyadenosine 5'-monophosphate
  • 2'-Deoxyadenosine 5'-phosphate
  • 2'-Deoxyadenosine monophosphate
  • 2'-deoxyadenosine-5'-monophosphate
  • 2'-deoxyadenosine-5'-phosphate
  • 2'-Deoxyadenylate
  • 2'-Deoxyadenylic acid
  • 3-(Dimethylamino)phenol
  • 3-Hydroxy-N,N-dimethylaniline
  • 5'-Adenylic acid, 2'-deoxy-
  • Adenosine, 2'-deoxy-, 5'-(dihydrogen phosphate)
  • Adenosine, 2'-deoxy-, 5'-phosphoric acid
  • dAMP
  • Deoxy-5'-adenylate
  • Deoxy-5'-adenylic acid
  • Deoxy-AMP
  • Deoxyadenosine 5'-monophosphate
  • Deoxyadenosine 5'-phosphate
  • deoxyadenosine monophosphate
  • deoxyadenosine-phosphate
  • Deoxyadenylate
  • deoxyadenylic acid
  • m-(Dimethylamino)phenol
  • N,N-Dimethyl-m-aminophenol
  • PdA
  • PdA (VAN)
  • Phenol, m-(dimethylamino)-
  • 2'-Deoxy-5'-adenosine monophosphoric acid
  • 2'-Deoxyadenosine 5'-(dihydrogen phosphoric acid)
  • 2'-Deoxyadenosine 5'-phosphoric acid
  • 2'-Deoxyadenosine monophosphoric acid
  • 2'-DEOXYADENOSINE-5'-monophosphoric acid
  • Deoxyadenosine 5'-monophosphoric acid
  • Deoxyadenosine 5'-phosphoric acid
  • 2'-Deoxyadenosine 5'-monophosphoric acid
  • Deoxyadenosine monophosphoric acid
  • 2'-Deoxy-5'-adenosine monophosphate, ammonium salt
  • 2'-Deoxy-5'-adenosine monophosphate, disodium salt
  • 2'Deoxy-5'-AMP
  • dAMP CPD
CAS number653-63-4
WeightAverage: 331.2218
Monoisotopic: 331.068169717
InChI KeyKHWCHTKSEGGWEX-RRKCRQDMSA-N
InChIInChI=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
IUPAC Name{[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid
Traditional IUPAC NameDAMP
Chemical FormulaC10H14N5O6P
SMILESNC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](COP(O)(O)=O)O1
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
Physical Properties
StateSolid
Charge0
Melting point148 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility2.71 g/LALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • mitochondrion
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG Pathways
Purine metabolismec00230 Map00230
SMPDB ReactionsNot Available
KEGG Reactions
3',5'-cyclic dAMP + waterdAMP + hydron
dAMP + waterphosphate + 2'-Deoxyadenosine
Adenosine triphosphate + dAMPdADP + ADP
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (6 TMS)splash10-001i-9210000000-52089369f69d88f5ea1cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-001i-9210000000-52089369f69d88f5ea1cJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0005-9601000000-2ae616924ca1385b9693JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-01ow-9433000000-7d0506e58e284d44779cJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0089-4096000000-d903c4b1613b2ac5f708JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9010000000-c50cec0a2ca71d42d524JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9300000000-8ebf385d33982fcaef9fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-001i-0209000000-05ded3b31c4db3d6c016JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-0019-1907000000-50567fa8c2638c9e2b6fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-003r-9804000000-9196bd87057cc65827a3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-003r-9804000000-9196bd87057cc65827a3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0209000000-05ded3b31c4db3d6c016JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0019-1907000000-50567fa8c2638c9e2b6fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-000i-2900000000-7eab9e6d466f6f6fc5caJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0019-1907000000-50567fa8c2638c9e2b6fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0019-4900000000-7e54c832e11165a43f06JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-000i-6900000000-2a484df957d9a58803cdJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-000i-4930000000-881e3633ecf1832b39c1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-0921000000-913b60e77094a1a288c9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-2900000000-ee54193845dfdd45afd8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-000i-1900000000-700554bbc39a72147ed1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0059-9500000000-f0950c77946a8c1b5112JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-000i-1930000000-a75e389060d82c5d0b7fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0901000000-2d08f4128523b3afc5f3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-3c531326eee979b1f9a3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900000000-e832807c09bda720138bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-6309000000-3c3e22257c611faa9f07JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9500000000-2304362c6bf7c8e4aa49JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-f628177d4207cc1a2c0bJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Gu, C., Wang, Y. (2007). "In vitro replication and thermodynamic studies of methylation and oxidation modifications of 6-thioguanine." Nucleic Acids Res 35:3693-3704.17517786
  • Ungar, L., Yosef, N., Sela, Y., Sharan, R., Ruppin, E., Kupiec, M. (2009). "A genome-wide screen for essential yeast genes that affect telomere length maintenance." Nucleic Acids Res 37:3840-3849.19386622
  • Nookaew, I., Jewett, M. C., Meechai, A., Thammarongtham, C., Laoteng, K., Cheevadhanarak, S., Nielsen, J., Bhumiratana, S. (2008). "The genome-scale metabolic model iIN800 of Saccharomyces cerevisiae and its validation: a scaffold to query lipid metabolism." BMC Syst Biol 2:71.18687109
Synthesis Reference:Scarano, E. Incorporation of adenine-C14 into deoxyadenylic acid. Bollettino - Societa Italiana di Biologia Sperimentale (1958), 34 1620-1.
External Links:
ResourceLink
CHEBI ID17713
HMDB IDHMDB00905
Pubchem Compound ID621
Kegg IDC00360
ChemSpider ID25056912
FOODB IDFDB022311
WikipediaDeoxyadenosine_monophosphate
BioCyc IDDAMP

Enzymes

General function:
Involved in catalytic activity
Specific function:
Controls the level of cAMP in yeast cells, together with the low-affinity cAMP phosphodiesterase (PDE1)
Gene Name:
PDE2
Uniprot ID:
P06776
Molecular weight:
60999.19922
Reactions
Adenosine 3',5'-cyclic phosphate + H(2)O → adenosine 5'-phosphate.

Transporters

General function:
Involved in binding
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
P40556
Molecular weight:
41954.0