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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:45 UTC
HMDB IDHMDB01044
Secondary Accession NumbersNone
Metabolite Identification
Common Name2'-Deoxyguanosine 5'-monophosphate
Description2'-Deoxyguanosine 5'-monophosphate is a derivative of the common nucleic acid GTP, or guanosine triphosphate, in which the -OH (hydroxyl) group on the 2' carbon on the nucleotide's pentose has been removed (hence the deoxy- part of the name). Additionally, the diphosphate of the name indicates that two of the phosphoryl groups of GTP have been removed, most likely by hydrolysis (Wikipedia).
Structure
Thumb
Synonyms
ValueSource
2'-Deoxy-GMPChEBI
2'-Deoxyguanosine 5'-(dihydrogen phosphate)ChEBI
2'-Deoxyguanosine 5'-monophosphateChEBI
2'-Deoxyguanosine 5'-phosphateChEBI
2'-Deoxyguanylic acidChEBI
2'-dGMPChEBI
Deoxy-GMPChEBI
Deoxyguanosine 5'-monophosphateChEBI
Deoxyguanosine 5'-phosphateChEBI
Deoxyguanosine monophosphateChEBI
Deoxyguanylic acidChEBI
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'-DeoxyguanylateHMDB
2'-DG-5'-MPHMDB
Deoxyguanosine-phosphateHMDB
dGMPHMDB
Guanine ribosideHMDB
Chemical FormulaC10H14N5O7P
Average Molecular Weight347.2212
Monoisotopic Molecular Weight347.063084339
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 Namedeoxyguanylate
CAS Registry Number902-04-5
SMILES
NC1=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](COP(O)(O)=O)O2)C(=O)N1
InChI Identifier
InChI=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 KeyInChIKey=LTFMZDNNPPEQNG-KVQBGUIXSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine ribonucleotides
Direct ParentPurine ribonucleoside monophosphates
Alternative Parents
Substituents
  • Purine ribonucleoside monophosphate
  • Hypoxanthine
  • 6-oxopurine
  • Purine
  • Imidazopyrimidine
  • Monoalkyl phosphate
  • Pyrimidone
  • Alkyl phosphate
  • Pyrimidine
  • Primary aromatic amine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-substituted imidazole
  • Saccharide
  • Heteroaromatic compound
  • Vinylogous amide
  • Oxolane
  • Imidazole
  • Azole
  • Secondary alcohol
  • Lactam
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
Biofunction
  • Component of Purine metabolism
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
  • Lysosome
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.7 mg/mLALOGPS
logP-1.9ALOGPS
logP-2.8ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.21ChemAxon
pKa (Strongest Basic)2.62ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area181.52 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity73.55 m3·mol-1ChemAxon
Polarizability29.86 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0fr2-0598000000-21b063e2aff7146d8568View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0udi-0900000000-d2858e957ac8a4c91e79View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-004j-9203000000-40bcf8d5e1ae6813c4f7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
  • Lysosome
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Adenine phosphoribosyltransferase deficiency (APRT)SMP00535Not Available
Adenosine Deaminase DeficiencySMP00144Not Available
Adenylosuccinate Lyase DeficiencySMP00167Not Available
AICA-RibosiduriaSMP00168Not Available
Azathioprine PathwaySMP00427Not Available
Gout or Kelley-Seegmiller SyndromeSMP00365Not Available
Lesch-Nyhan Syndrome (LNS)SMP00364Not Available
Mercaptopurine PathwaySMP00428Not Available
Mitochondrial DNA depletion syndromeSMP00536Not Available
Molybdenum Cofactor DeficiencySMP00203Not Available
Myoadenylate deaminase deficiencySMP00537Not Available
Purine MetabolismSMP00050map00230
Purine Nucleoside Phosphorylase DeficiencySMP00210Not Available
Thioguanine PathwaySMP00430Not Available
Xanthine Dehydrogenase Deficiency (Xanthinuria)SMP00220Not Available
Xanthinuria type ISMP00512Not Available
Xanthinuria type IISMP00513Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022388
KNApSAcK IDNot Available
Chemspider ID58570
KEGG Compound IDC00362
BioCyc IDDGMP
BiGG ID34744
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01044
Metagene LinkHMDB01044
METLIN IDNot Available
PubChem Compound65059
PDB IDDG
ChEBI ID16192
References
Synthesis ReferenceReichard, Peter. Formation of deoxyguanosine 5'-phosphate from guanosine 5'-phosphate with enzymes from chick embryos. Biochimica et Biophysica Acta (1960), 41 368-9.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Warnecke A, Fichtner I, Garmann D, Jaehde U, Kratz F: Synthesis and biological activity of water-soluble maleimide derivatives of the anticancer drug carboplatin designed as albumin-binding prodrugs. Bioconjug Chem. 2004 Nov-Dec;15(6):1349-59. [15546202 ]

Enzymes

General function:
Involved in ATP binding
Specific function:
Required for the phosphorylation of several deoxyribonucleosides and certain nucleoside analogs widely employed as antiviral and chemotherapeutic agents.
Gene Name:
DGUOK
Uniprot ID:
Q16854
Molecular weight:
32055.53
Reactions
Adenosine triphosphate + Deoxyguanosine → ADP + 2'-Deoxyguanosine 5'-monophosphatedetails
General function:
Involved in hydrolase activity
Specific function:
Pyrophosphatase that hydrolyzes the non-canonical purine nucleotides inosine triphosphate (ITP), deoxyinosine triphosphate (dITP) as well as 2'-deoxy-N-6-hydroxylaminopurine triposphate (dHAPTP) and xanthosine 5'-triphosphate (XTP) to their respective monophosphate derivatives. The enzyme does not distinguish between the deoxy- and ribose forms. Probably excludes non-canonical purines from RNA and DNA precursor pools, thus preventing their incorporation into RNA and DNA and avoiding chromosomal lesions.
Gene Name:
ITPA
Uniprot ID:
Q9BY32
Molecular weight:
16833.23
Reactions
dGTP + Water → 2'-Deoxyguanosine 5'-monophosphate + Pyrophosphatedetails
General function:
Involved in guanylate kinase activity
Specific function:
Essential for recycling GMP and indirectly, cGMP.
Gene Name:
GUK1
Uniprot ID:
Q16774
Molecular weight:
21725.41
Reactions
Adenosine triphosphate + 2'-Deoxyguanosine 5'-monophosphate → ADP + dGDPdetails
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
Reactions
2'-Deoxyguanosine 5'-monophosphate + Water → Deoxyguanosine + Phosphoric aciddetails
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
Reactions
2'-Deoxyguanosine 5'-monophosphate + Water → Deoxyguanosine + Phosphoric aciddetails
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
Reactions
2'-Deoxyguanosine 5'-monophosphate + Water → Deoxyguanosine + Phosphoric aciddetails
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
Reactions
2'-Deoxyguanosine 5'-monophosphate + Water → Deoxyguanosine + Phosphoric aciddetails
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
Reactions
2'-Deoxyguanosine 5'-monophosphate + Water → Deoxyguanosine + Phosphoric aciddetails
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:
P49902
Molecular weight:
64969.2
Reactions
2'-Deoxyguanosine 5'-monophosphate + Water → Deoxyguanosine + Phosphoric aciddetails
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
Reactions
2'-Deoxyguanosine 5'-monophosphate + Water → Deoxyguanosine + Phosphoric aciddetails