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Showing Compound 2'-Deoxyguanosine 5'-monophosphate (FDB022388)

Record Information
Version1.0
Creation date2011-09-21 00:13:15 UTC
Update date2020-09-17 15:38:46 UTC
Primary IDFDB022388
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2'-Deoxyguanosine 5'-monophosphate
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. Within humans, 2'-deoxyguanosine 5'-monophosphate participates in a number of enzymatic reactions. In particular, 2'-deoxyguanosine 5'-monophosphate can be converted into dGDP; which is mediated by the enzyme guanylate kinase. In addition, 2'-deoxyguanosine 5'-monophosphate can be converted into deoxyguanosine through its interaction with the enzyme cytosolic purine 5'-nucleotidase. In humans, 2'-deoxyguanosine 5'-monophosphate is involved in the metabolic disorder called the gout or kelley-seegmiller syndrome pathway. A purine 2'-deoxyribonucleoside 5'-monophosphate having guanine as the nucleobase.
CAS Number902-04-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
2'-Deoxy-GMPChEBI
2'-Deoxyguanosine 5'-(dihydrogen phosphate)ChEBI
2'-Deoxyguanosine 5'-phosphateChEBI
2'-Deoxyguanylic acidChEBI
2'-dGMPChEBI
Deoxy-GMPChEBI
Deoxyguanosine 5'-monophosphateChEBI
Deoxyguanosine 5'-phosphateChEBI
Deoxyguanosine monophosphateChEBI
Deoxyguanylic acidChEBI
dGMPChEBI
2'-Deoxyguanosine 5'-(dihydrogen phosphoric acid)Generator
2'-Deoxyguanosine 5'-phosphoric acidGenerator
2'-DeoxyguanylateGenerator
Deoxyguanosine 5'-monophosphoric acidGenerator
Deoxyguanosine 5'-phosphoric acidGenerator
Deoxyguanosine monophosphoric acidGenerator
DeoxyguanylateGenerator
2'-Deoxyguanosine 5'-monophosphoric acidGenerator
2'-Deoxy-5'-GMPHMDB
2'-Deoxy-5'-guanylateHMDB
2'-Deoxy-5'-guanylic acidHMDB
2'-Deoxy-guanosine 5'-(dihydrogen phosphate)HMDB
2'-Deoxy-guanosine 5'-phosphateHMDB
2'-Deoxy-guanosine phosphateHMDB
2'-Deoxyguanosine-5'-phosphateHMDB
2'-DG-5'-MPHMDB
Deoxyguanosine-phosphateHMDB
Guanine ribosideHMDB
2'-Deoxyguanosine 5'-phosphate, ion (1+)HMDB
2'-Deoxyguanosine 5'-phosphate, disodium saltHMDB
2'-Deoxy-guanosine 5'-(dihydrogen ate)HMDB
2'-deoxy-Guanosine 5'-(dihydrogen phosphate)hmdb
2'-Deoxy-guanosine 5'-ateHMDB
2'-deoxy-Guanosine 5'-phosphatehmdb
2'-Deoxy-guanosine ateHMDB
2'-deoxy-Guanosine phosphatehmdb
2'-Deoxyguanosine 5'-(dihydrogen ate)ChEBI
2'-Deoxyguanosine 5'-(dihydrogen ic acid)Generator
2'-Deoxyguanosine 5'-ateChEBI
2'-Deoxyguanosine 5'-ic acidGenerator
2'-Deoxyguanosine 5'-monoateChEBI
2'-Deoxyguanosine 5'-monoic acidGenerator
2'-Deoxyguanosine 5'-monophosphatehmdb
2'-Deoxyguanosine 5'-monophosphic acidhmdb
2'-Deoxyguanosine-5'-ateHMDB
2'-deoxyguanosine-5'-phosphatehmdb
2'-dG-5'-MPhmdb
Deoxyguanosine 5'-ateChEBI
Deoxyguanosine 5'-ic acidGenerator
Deoxyguanosine 5'-monoateChEBI
Deoxyguanosine 5'-monoic acidGenerator
Deoxyguanosine monoateChEBI
Deoxyguanosine monoic acidGenerator
Deoxyguanosine-ateHMDB
deoxyguanosine-phosphatehmdb
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H14N5O7P
IUPAC name{[(2R,3S,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid
InChI IdentifierInChI=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
InChI KeyLTFMZDNNPPEQNG-KVQBGUIXSA-N
Isomeric SMILESNC1=NC(=O)C2=C(N1)N(C=N2)[C@H]1C[C@H](O)[C@@H](COP(O)(O)=O)O1
Average Molecular Weight347.2212
Monoisotopic Molecular Weight347.063084339
Classification
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
Ontology
Disposition

Biological location:

Source:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS2'-Deoxyguanosine 5'-monophosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-9412000000-b0aa92c3ffa6b5b0890cSpectrum
Predicted GC-MS2'-Deoxyguanosine 5'-monophosphate, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03dm-9422100000-bc551a9549f9ae975b71Spectrum
Predicted GC-MS2'-Deoxyguanosine 5'-monophosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0fr2-0598000000-21b063e2aff7146d85682012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0udi-0900000000-d2858e957ac8a4c91e792012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-004j-9203000000-40bcf8d5e1ae6813c4f72012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004j-9203000000-40bcf8d5e1ae6813c4f72017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0900000000-dab30b9a6de3477fa70e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-002b-6109000000-6e5f13e1030d907bf4502021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-004i-9200000000-c3273057674f4f74157b2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-002b-6009000000-303a1b69aa5c35e59b532021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-004i-9200000000-5a760c04146b7ec031d72021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-004i-9300000000-d435ed7c5cdb985296822021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-41c0a9342f54a46fa4e42021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-000i-2900000000-68f72700dfdbb0374a852021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000j-0905000000-26458e3261a5441d93042021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0udr-1900000000-7a7e7e8e0b0145b7230d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0udi-1900000000-a0ce6815866f122bcce02021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-0901000000-415ae3ba37bc56d4a4022021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-000i-1900000000-bd375d50d1fb3f2364682021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-6585941fd6af257d9a962021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-000i-2900000000-303e1f2bb06730d8520d2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0901000000-e4234086a26601ce5af32016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-566d720734de1bad5cd62016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0900000000-5d4689698c352d2a2f452016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002b-6309000000-10f0b25fe6368edd16602016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9500000000-d531006102bbcb9090d12016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-a08be881b0ccce87df8a2016-09-12View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID58570
ChEMBL IDCHEMBL477487
KEGG Compound IDC00362
Pubchem Compound ID65059
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB04457
HMDB IDHMDB01044
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID34744
KNApSAcK IDNot Available
HET IDDG
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Cytosolic 5'-nucleotidase 3NT5C3Q9H0P0
Deoxyguanosine kinase, mitochondrialDGUOKQ16854
Guanylate kinaseGUK1Q16774
Pathways
NameSMPDB LinkKEGG Link
Purine MetabolismSMP00050 map00230
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference