Structural search and advanced query search is temporarily unavailable. We are working to fix this issue. Thank you for your support and patience.


8-Hydroxydeoxyguanosine 5'-triphosphate (M2MDB001089)

Record Information
Version2.0
Creation Date2012-05-31 14:35:05 -0600
Update Date2015-06-03 17:19:37 -0600
Secondary Accession Numbers
  • ECMDB20246
Identification
Name:8-Hydroxydeoxyguanosine 5'-triphosphate
Description8-hydroxydeoxyguanosine 5'-triphosphate (8-hydroxy-dGTP) is a member of the chemical class known as Purine 2'-deoxyribonucleoside Triphosphates. These are purine nucleotides with triphosphate group linked to the ribose moiety lacking an hydroxyl group at position 2. Hydroxylated nucleotides can appear in DNA that has been oxidatively damaged. Escherichia coli Orf135 protein is thought to be an enzyme that efficiently hydrolyzes oxidatively damaged nucleotides such as 2-hydroxy-dATP, 8-hydroxy-dGTP and 5-hydroxy-CTP, in addition to 5-methyl-dCTP, dCTP and CTP, thus preventing mutations in cells caused by unfavorable base pairing. [PMID:21553121]
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 8-Hydroxydeoxyguanosine 5'-triphosphoric acid
  • 8-HYDROXYDEOXYGUANOSINE-5-TRIPHOSPHAT
Chemical Formula:C10H12N5O14P3
Weight:Average: 519.1487
Monoisotopic: 518.959359653
InChI Key:BUZOGVVQWCXXDP-UHFFFAOYSA-J
InChI:InChI=1S/C10H16N5O14P3/c11-9-13-7-6(8(17)14-9)12-10(18)15(7)5-1-3(16)4(27-5)2-26-31(22,23)29-32(24,25)28-30(19,20)21/h3-5,16H,1-2H2,(H,12,18)(H,22,23)(H,24,25)(H2,19,20,21)(H3,11,13,14,17)/p-4
CAS number:Not Available
IUPAC Name:9-[4-hydroxy-5-({[hydroxy({[hydroxy(phosphonatooxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-2-yl]-2-imino-3,9-dihydro-2H-purine-6,8-bis(olate)
Traditional IUPAC Name:9-{4-hydroxy-5-[({hydroxy[hydroxy(phosphonatooxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-2-yl}-2-imino-3H-purine-6,8-bis(olate)
SMILES:OC1CC(OC1COP(O)(=O)OP(O)(=O)OP([O-])([O-])=O)N1C([O-])=NC2=C1NC(=N)N=C2[O-]
Chemical Taxonomy
Description belongs to the class of organic compounds 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.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine deoxyribonucleotides
Direct ParentPurine 2'-deoxyribonucleoside triphosphates
Alternative Parents
Substituents
  • Purine 2'-deoxyribonucleoside triphosphate
  • 6-oxopurine
  • Hypoxanthine
  • Purinone
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Pyrimidone
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Pyrimidine
  • Alkyl phosphate
  • Heteroaromatic compound
  • Azole
  • Imidazole
  • Vinylogous amide
  • Tetrahydrofuran
  • Secondary alcohol
  • Urea
  • Azacycle
  • Oxacycle
  • Organoheterocyclic compound
  • Alcohol
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Organic nitrogen compound
  • Amine
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic anion
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility10.7 g/LALOGPS
logP-0.75ALOGPS
logP-2.2ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)0.9ChemAxon
pKa (Strongest Basic)5.36ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area307.12 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity126.62 m³·mol⁻¹ChemAxon
Polarizability38.15 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0100090000-4e2d94b1c5ffc51d526eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uki-1001790000-c45449fc4bb87a6ad0c0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fmi-4950020000-ea527b1b10fda9ea8f65View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000090000-a4f10fd804f9d4faaddbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-5100090000-da8269f836220a8f7da5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9400000000-9321064ffc4ec1a09714View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Kawasaki, K., Yoneyama, M., Murata-Kamiya, N., Harashima, H., Kojima, C., Ito, Y., Kamiya, H., Mishima, M. (2012). "(1)H, (1)(3)C and (1)(5)N NMR assignments of the Escherichia coli Orf135 protein." Biomol NMR Assign 6:1-4. Pubmed: 21553121
  • 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
  • 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)Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound ID25201462
Kegg IDNot Available
ChemSpider ID24784983
Wikipedia IDNot Available
BioCyc ID8-HYDROXYDEOXYGUANOSINE-5-TRIPHOSPHAT
EcoCyc ID8-HYDROXYDEOXYGUANOSINE-5-TRIPHOSPHAT

Enzymes

Protein Details
1. CTP pyrophosphohydrolase
General function:
Involved in hydrolase activity
Specific function:
Specific for pyrimidine substrates. Acts on 5-methyl- dCTP, CTP and dCTP in decreasing order
Gene Name:
nudG
Uniprot ID:
P77788
Molecular weight:
15046
Reactions
CTP + H(2)O = CMP + diphosphate.