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Identification
YMDB IDYMDB00506
NamedGMP
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description2'-Deoxyguanosine 5'-monophosphate, also known as deoxyguanylic acid or 2'-deoxy-GMP, 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. 2'-Deoxyguanosine 5'-monophosphate is a moderately basic compound (based on its pKa). 2'-Deoxyguanosine 5'-monophosphate exists in all living species, ranging from bacteria to humans.
Structure
Thumb
Synonyms
  • 2-deoxyguanosine 5-monophosphate
  • 2-deoxyguanosine 5-phosphate
  • 2'-Deoxy-5'-GMP
  • 2'-Deoxy-5'-guanylate
  • 2'-Deoxy-5'-guanylic acid
  • 2'-Deoxy-GMP
  • 2'-deoxy-Guanosine 5'-(dihydrogen phosphate)
  • 2'-deoxy-Guanosine 5'-phosphate
  • 2'-deoxy-Guanosine phosphate
  • 2'-Deoxyguanosine 5'-monophosphate
  • 2'-Deoxyguanosine 5'-monophosphic acid
  • 2'-Deoxyguanosine 5'-phosphate
  • 2'-Deoxyguanosine 5'-phosphoric acid
  • 2'-Deoxyguanosine 5'MP
  • 2'-deoxyguanosine-5'-phosphate
  • 2'-Deoxyguanylate
  • 2'-Deoxyguanylic acid
  • 2'-dG-5'-MP
  • 2'-dGMP
  • 5'-Deoxyguanylic acid
  • 5'-DGMP
  • 5'-Guanylic acid, 2'-deoxy-
  • Deoxy GMP
  • Deoxy-GMP
  • Deoxyguanosine 5'-monophosphate
  • Deoxyguanosine 5'-phosphate
  • deoxyguanosine monophosphate
  • deoxyguanosine-phosphate
  • deoxyguanylic acid
  • dGMP
  • DGP
  • guanine riboside
  • Guanosine, 2'-deoxy-, 5'-(dihydrogen phosphate)
  • Guanosine, 2'-deoxy-, 5'-phosphoric acid
  • 2'-Deoxyguanosine 5'-(dihydrogen phosphate)
  • 2'-Deoxyguanosine 5'-(dihydrogen phosphoric acid)
  • Deoxyguanosine 5'-monophosphoric acid
  • Deoxyguanosine 5'-phosphoric acid
  • Deoxyguanosine monophosphoric acid
  • Deoxyguanylate
  • 2'-Deoxyguanosine 5'-monophosphoric acid
  • 2'-Deoxyguanosine 5'-phosphate, ion (1+)
  • 2'-Deoxyguanosine 5'-phosphate, disodium salt
CAS number902-04-5
WeightAverage: 347.2212
Monoisotopic: 347.063084339
InChI KeyLTFMZDNNPPEQNG-KVQBGUIXSA-N
InChIInChI=1S/C10H14N5O7P/c11-10-13-8-7(9(17)14-10)12-3-15(8)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
IUPAC Name{[(2R,3S,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Namedeoxyguanylate
Chemical FormulaC10H14N5O7P
SMILESNC1=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](COP(O)(O)=O)O2)C(=O)N1
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
  • Imidazopyrimidine
  • Purine
  • Hydroxypyrimidine
  • Monoalkyl phosphate
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Pyrimidine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Secondary alcohol
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility2.7 g/LALOGPS
logP-1.9ALOGPS
logP-2.8ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.21ChemAxon
pKa (Strongest Basic)2.62ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area181.52 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity73.55 m³·mol⁻¹ChemAxon
Polarizability29.72 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
water + dGMP2'-Deoxyguanosine + phosphate
Adenosine triphosphate + dGMPADP + dGDP
water + dGDPphosphate + hydron + dGMP
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9412000000-b0aa92c3ffa6b5b0890cJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-03dm-9422100000-bc551a9549f9ae975b71JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0fr2-0598000000-21b063e2aff7146d8568JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0udi-0900000000-d2858e957ac8a4c91e79JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-004j-9203000000-40bcf8d5e1ae6813c4f7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004j-9203000000-40bcf8d5e1ae6813c4f7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0900000000-dab30b9a6de3477fa70eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0901000000-e4234086a26601ce5af3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-566d720734de1bad5cd6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0900000000-5d4689698c352d2a2f45JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002b-6309000000-10f0b25fe6368edd1660JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9500000000-d531006102bbcb9090d1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-a08be881b0ccce87df8aJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H 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
  • 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:Reichard, Peter. Formation of deoxyguanosine 5'-phosphate from guanosine 5'-phosphate with enzymes from chick embryos. Biochimica et Biophysica Acta (1960), 41 368-9.
External Links:
ResourceLink
CHEBI ID16192
HMDB IDHMDB01044
Pubchem Compound ID65059
Kegg IDC00362
ChemSpider ID24604718
FOODB IDFDB022388
WikipediaDeoxyguanosine_monophosphate
BioCyc IDDGMP

Enzymes

General function:
Involved in protein binding
Specific function:
Essential for recycling GMP and indirectly, cGMP
Gene Name:
GUK1
Uniprot ID:
P15454
Molecular weight:
20637.19922
Reactions
ATP + GMP → ADP + GDP.

Transporters

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