Record Information
Version2.0
Creation Date2012-05-31 13:52:48 -0600
Update Date2015-09-13 12:56:11 -0600
Secondary Accession Numbers
  • ECMDB01440
Identification
Name:dGTP
Description:dGTP is one of the two purine nucleotides that are used to synthesize DNA. It is an intermediate in purine metabolism pathway. It is a product of anaerobic ribonucleoside-triphosphate reductase (EC:1.17.4.2) and a substrate of deoxyguanosine triphosphate triphosphohydrolase (EC:3.1.5.1). (KEGG)
Structure
Thumb
Synonyms:
  • 2'-Deoxyguanosine 5'-triphosphate
  • 2'-Deoxyguanosine 5'-triphosphoric acid
  • 2'-Deoxyguanosine triphosphate
  • 2'-Deoxyguanosine triphosphoric acid
  • 2'-Deoxyguanosine-5'-triphosphate
  • 2'-Deoxyguanosine-5'-triphosphoric acid
  • Deoxy-GTP
  • Deoxyguanosine 5'-triphosphate
  • Deoxyguanosine 5'-triphosphoric acid
  • Deoxyguanosine triphosphate
  • Deoxyguanosine triphosphoric acid
  • Deoxyguanosine-triphosphate
  • Deoxyguanosine-triphosphoric acid
  • DGTP
Chemical Formula:C10H16N5O13P3
Weight:Average: 507.181
Monoisotopic: 506.995745159
InChI Key:HAAZLUGHYHWQIW-KVQBGUIXSA-N
InChI:InChI=1S/C10H16N5O13P3/c11-10-13-8-7(9(17)14-10)12-3-15(8)6-1-4(16)5(26-6)2-25-30(21,22)28-31(23,24)27-29(18,19)20/h3-6,16H,1-2H2,(H,21,22)(H,23,24)(H2,18,19,20)(H3,11,13,14,17)/t4-,5+,6+/m0/s1
CAS number:2564-35-4
IUPAC Name:({[({[(2R,3S,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
Traditional IUPAC Name:dGTP
SMILES:NC1=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O2)C(=O)N1
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as purine 2'-deoxyribonucleoside triphosphates. These are purine nucleotides with triphosphate group linked to the ribose moiety lacking a hydroxyl group at position 2.
KingdomChemical entities
Super ClassOrganic compounds
ClassNucleosides, nucleotides, and analogues
Sub ClassPurine nucleotides
Direct ParentPurine 2'-deoxyribonucleoside triphosphates
Alternative Parents
Substituents
  • Purine 2'-deoxyribonucleoside triphosphate
  • Imidazopyrimidine
  • Purine
  • Monoalkyl phosphate
  • Hydroxypyrimidine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Pyrimidine
  • Alkyl phosphate
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Oxolane
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility5.59 mg/mLALOGPS
logP-0.61ALOGPS
logP-2.8ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)1.61ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area274.58 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity95.73 m3·mol-1ChemAxon
Polarizability39.1 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Pyrimidine metabolismPW000942 Pw000942Pw000942 greyscalePw000942 simple
purine nucleotides de novo biosynthesisPW000910 Pw000910Pw000910 greyscalePw000910 simple
purine nucleotides de novo biosynthesis 1435709748PW000960 Pw000960Pw000960 greyscalePw000960 simple
purine nucleotides de novo biosynthesis 2PW002033 Pw002033Pw002033 greyscalePw002033 simple
KEGG Pathways:
EcoCyc Pathways:
  • guanosine nucleotides de novo biosynthesis PWY-6125
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSsplash10-054n-9663300000-69b95474f5eb453321beView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0002-9630410000-325219a8d4bf19fde6eeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0910100000-0b4a31d8c636c368a5aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-1158073094ef9de8ec75View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0900000000-4330d672c10b6546947eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0330290000-f951ce7240e0b3c9bb63View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fb9-7940100000-9f33838fecee36769f00View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-9710000000-e1ba8d1db7700c321064View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Kicska GA, Long L, Horig H, Fairchild C, Tyler PC, Furneaux RH, Schramm VL, Kaufman HL: Immucillin H, a powerful transition-state analog inhibitor of purine nucleoside phosphorylase, selectively inhibits human T lymphocytes. Proc Natl Acad Sci U S A. 2001 Apr 10;98(8):4593-8. Epub 2001 Apr 3. Pubmed: 11287638
  • Stoop JW, Zegers BJ, Hendrickx GF, van Heukelom LH, Staal GE, de Bree PK, Wadman SK, Ballieux RE: Purine nucleoside phosphorylase deficiency associated with selective cellular immunodeficiency. N Engl J Med. 1977 Mar 24;296(12):651-5. Pubmed: 402573
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID16497
HMDB IDHMDB01440
Pubchem Compound ID65103
Kegg IDC00286
ChemSpider ID58613
WikipediaDeoxyguanosine triphosphate
BioCyc IDDGTP
EcoCyc IDDGTP
Ligand ExpoDGT

Enzymes

General function:
Involved in nucleic acid binding
Specific function:
In addition to polymerase activity, this DNA polymerase exhibits 3' to 5' and 5' to 3' exonuclease activity. It is able to utilize nicked circular duplex DNA as a template and can unwind the parental DNA strand from its template
Gene Name:
polA
Uniprot ID:
P00582
Molecular weight:
103117
Reactions
Deoxynucleoside triphosphate + DNA(n) = diphosphate + DNA(n+1).
General function:
Involved in DNA binding
Specific function:
DNA polymerase III is a complex, multichain enzyme responsible for most of the replicative synthesis in bacteria. The epsilon subunit contain the editing function and is a proofreading 3'-5' exonuclease
Gene Name:
dnaQ
Uniprot ID:
P03007
Molecular weight:
27099
Reactions
Deoxynucleoside triphosphate + DNA(n) = diphosphate + DNA(n+1).
General function:
Involved in nucleotide binding
Specific function:
The gamma chain seems to interact with the delta subunit to transfer the beta subunit on the DNA
Gene Name:
dnaX
Uniprot ID:
P06710
Molecular weight:
71137
Reactions
Deoxynucleoside triphosphate + DNA(n) = diphosphate + DNA(n+1).
General function:
Involved in nucleoside diphosphate kinase activity
Specific function:
Major role in the synthesis of nucleoside triphosphates other than ATP. The ATP gamma phosphate is transferred to the NDP beta phosphate via a ping-pong mechanism, using a phosphorylated active-site intermediate
Gene Name:
ndk
Uniprot ID:
P0A763
Molecular weight:
15463
Reactions
ATP + nucleoside diphosphate = ADP + nucleoside triphosphate.
General function:
Involved in ATP binding
Specific function:
ATP + uridine = ADP + UMP
Gene Name:
udk
Uniprot ID:
P0A8F4
Molecular weight:
24353
Reactions
ATP + uridine = ADP + UMP.
ATP + cytidine = ADP + CMP.
General function:
Involved in DNA binding
Specific function:
DNA polymerase III is a complex, multichain enzyme responsible for most of the replicative synthesis in bacteria. This DNA polymerase also exhibits 3' to 5' exonuclease activity. The beta chain is required for initiation of replication once it is clamped onto DNA, it slides freely (bidirectional and ATP- independent) along duplex DNA
Gene Name:
dnaN
Uniprot ID:
P0A988
Molecular weight:
40586
Reactions
Deoxynucleoside triphosphate + DNA(n) = diphosphate + DNA(n+1).
General function:
Involved in [formate-C-acetyltransferase]-activating enzyme activity
Specific function:
Activation of anaerobic ribonucleoside-triphosphate reductase under anaerobic conditions by generation of an organic free radical, using S-adenosylmethionine and reduced flavodoxin as cosubstrates to produce 5'-deoxy-adenosine
Gene Name:
nrdG
Uniprot ID:
P0A9N8
Molecular weight:
17446
General function:
Involved in DNA binding
Specific function:
The exact function of the theta subunit is unknown
Gene Name:
holE
Uniprot ID:
P0ABS8
Molecular weight:
8846
Reactions
Deoxynucleoside triphosphate + DNA(n) = diphosphate + DNA(n+1).
General function:
Involved in magnesium ion binding
Specific function:
ATP + pyruvate = ADP + phosphoenolpyruvate
Gene Name:
pykF
Uniprot ID:
P0AD61
Molecular weight:
50729
Reactions
ATP + pyruvate = ADP + phosphoenolpyruvate.
General function:
Involved in nucleoside-triphosphate diphosphatase activity
Specific function:
Specific function unknown
Gene Name:
mazG
Uniprot ID:
P0AEY3
Molecular weight:
30412
Reactions
ATP + H(2)O = AMP + diphosphate.
General function:
Involved in 3'-5' exonuclease activity
Specific function:
DNA polymerase III is a complex, multichain enzyme responsible for most of the replicative synthesis in bacteria. This DNA polymerase also exhibits 3' to 5' exonuclease activity. The alpha chain is the DNA polymerase
Gene Name:
dnaE
Uniprot ID:
P10443
Molecular weight:
129903
Reactions
Deoxynucleoside triphosphate + DNA(n) = diphosphate + DNA(n+1).
General function:
Involved in magnesium ion binding
Specific function:
dGTPase preferentially hydrolyzes dGTP over the other canonical NTPs
Gene Name:
dgt
Uniprot ID:
P15723
Molecular weight:
59382
Reactions
dGTP + H(2)O = deoxyguanosine + triphosphate.
General function:
Involved in magnesium ion binding
Specific function:
ATP + pyruvate = ADP + phosphoenolpyruvate
Gene Name:
pykA
Uniprot ID:
P21599
Molecular weight:
51357
Reactions
ATP + pyruvate = ADP + phosphoenolpyruvate.
General function:
Involved in DNA binding
Specific function:
DNA polymerase III is a complex, multichain enzyme responsible for most of the replicative synthesis in bacteria. This DNA polymerase also exhibits 3' to 5' exonuclease activity. The delta subunit seems to interact with the gamma subunit to transfer the beta subunit on the DNA
Gene Name:
holA
Uniprot ID:
P28630
Molecular weight:
38703
Reactions
Deoxynucleoside triphosphate + DNA(n) = diphosphate + DNA(n+1).
General function:
Involved in DNA binding
Specific function:
DNA polymerase III is a complex, multichain enzyme responsible for most of the replicative synthesis in bacteria. This DNA polymerase also exhibits 3' to 5' exonuclease activity
Gene Name:
holB
Uniprot ID:
P28631
Molecular weight:
36936
Reactions
Deoxynucleoside triphosphate + DNA(n) = diphosphate + DNA(n+1).
General function:
Involved in DNA-directed DNA polymerase activity
Specific function:
DNA polymerase III is a complex, multichain enzyme responsible for most of the replicative synthesis in bacteria. This DNA polymerase also exhibits 3' to 5' exonuclease activity. The exact function of the psi subunit is unknown
Gene Name:
holD
Uniprot ID:
P28632
Molecular weight:
15174
Reactions
Deoxynucleoside triphosphate + DNA(n) = diphosphate + DNA(n+1).
General function:
Involved in oxidoreductase activity
Specific function:
Transports electrons between flavodoxin or ferredoxin and NADPH. Involved in the reductive activation of cobalamin- independent methionine synthase, pyruvate formate lyase and anaerobic ribonucleotide reductase. Also protects against superoxide radicals due to methyl viologen in the presence of oxygen
Gene Name:
fpr
Uniprot ID:
P28861
Molecular weight:
27751
Reactions
2 reduced ferredoxin + NADP(+) + H(+) = 2 oxidized ferredoxin + NADPH.
General function:
Involved in catalytic activity
Specific function:
2'-deoxyribonucleoside triphosphate + thioredoxin disulfide + H(2)O = ribonucleoside triphosphate + thioredoxin
Gene Name:
nrdD
Uniprot ID:
P28903
Molecular weight:
80022
Reactions
2'-deoxyribonucleoside triphosphate + thioredoxin disulfide + H(2)O = ribonucleoside triphosphate + thioredoxin.
General function:
Involved in DNA binding
Specific function:
DNA polymerase III is a complex, multichain enzyme responsible for most of the replicative synthesis in bacteria. This DNA polymerase also exhibits 3' to 5' exonuclease activity
Gene Name:
holC
Uniprot ID:
P28905
Molecular weight:
16633
Reactions
Deoxynucleoside triphosphate + DNA(n) = diphosphate + DNA(n+1).
General function:
Involved in hydrolase activity
Specific function:
Hydrolyzes O6 atom-containing purine bases deoxyinosine triphosphate (dITP) and xanthosine triphosphate (XTP) as well as 2'-deoxy-N-6-hydroxylaminopurine triposphate (dHAPTP) to nucleotide monophosphate and pyrophosphate. Probably excludes non- standard purines from DNA precursor pool, preventing thus incorporation into DNA and avoiding chromosomal lesions
Gene Name:
rdgB
Uniprot ID:
P52061
Molecular weight:
21039
Reactions
A nucleoside triphosphate + H(2)O = a nucleotide + diphosphate.
General function:
Involved in ATP binding
Specific function:
Catalyzes the reversible transfer of the terminal phosphate group between ATP and AMP. This small ubiquitous enzyme involved in the energy metabolism and nucleotide synthesis, is essential for maintenance and cell growth
Gene Name:
adk
Uniprot ID:
P69441
Molecular weight:
23586
Reactions
ATP + AMP = 2 ADP.
General function:
Involved in FMN binding
Specific function:
Low-potential electron donor to a number of redox enzymes (Potential)
Gene Name:
fldB
Uniprot ID:
P0ABY4
Molecular weight:
19700
General function:
Involved in FMN binding
Specific function:
Low-potential electron donor to a number of redox enzymes (Potential). Involved in the reactivation of inactive cob(II)alamin in methionine synthase
Gene Name:
fldA
Uniprot ID:
P61949
Molecular weight:
19737
General function:
Replication, recombination and repair
Specific function:
Involved in the GO system responsible for removing an oxidatively damaged form of guanine (7,8-dihydro-8-oxoguanine) from DNA and the nucleotide pool. 8-oxo-dGTP is inserted opposite dA and dC residues of template DNA with almost equal efficiency thus leading to A.T to G.C transversions. MutT specifically degrades 8-oxo-dGTP to the monophosphate
Gene Name:
mutT
Uniprot ID:
P08337
Molecular weight:
14927
Reactions
8-oxo-dGTP + H(2)O = 8-oxo-dGMP + diphosphate.

Transporters

General function:
Involved in nucleoside diphosphate kinase activity
Specific function:
Major role in the synthesis of nucleoside triphosphates other than ATP. The ATP gamma phosphate is transferred to the NDP beta phosphate via a ping-pong mechanism, using a phosphorylated active-site intermediate
Gene Name:
ndk
Uniprot ID:
P0A763
Molecular weight:
15463
Reactions
ATP + nucleoside diphosphate = ADP + nucleoside triphosphate.