Np mrd loader

Record Information
Version2.0
Created at2024-09-11 23:12:36 UTC
Updated at2024-09-11 23:12:37 UTC
NP-MRD IDNP0339717
Secondary Accession NumbersNone
Natural Product Identification
Common Name8-oxo-GTP
Description8-Oxo-GTP belongs to the class of organic compounds known as purine ribonucleoside triphosphates. These are purine ribobucleotides with a triphosphate group linked to the ribose moiety. 8-oxo-GTP was first documented in 2013 (PMID: 23463507). Based on a literature review a significant number of articles have been published on 8-oxo-GTP (PMID: 38776712) (PMID: 38657843) (PMID: 36746255) (PMID: 36139879) (PMID: 35809767) (PMID: 33021500).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC10H12N5O15P3
Average Mass535.1490 Da
Monoisotopic Mass534.95647 Da
IUPAC Name({[5-(2-amino-6,8-dioxo-6,7,8,9-tetrahydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy)(phosphonatooxy)phosphinate
Traditional Name{[5-(2-amino-6,8-dioxo-1,7-dihydropurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy(phosphonatooxy)phosphinate
CAS Registry NumberNot Available
SMILES
NC1=NC2=C(NC(=O)N2C2OC(COP([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O)C(O)C2O)C(=O)N1
InChI Identifier
InChI=1/C10H16N5O15P3/c11-9-13-6-3(7(18)14-9)12-10(19)15(6)8-5(17)4(16)2(28-8)1-27-32(23,24)30-33(25,26)29-31(20,21)22/h2,4-5,8,16-17H,1H2,(H,12,19)(H,23,24)(H,25,26)(H2,20,21,22)(H3,11,13,14,18)/p-4
InChI KeyJCHLKIQZUXYLPW-UHFFFAOYNA-J
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as purine ribonucleoside triphosphates. These are purine ribobucleotides with a triphosphate group linked to the ribose moiety.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine ribonucleotides
Direct ParentPurine ribonucleoside triphosphates
Alternative Parents
Substituents
  • Purine ribonucleoside triphosphate
  • Purine ribonucleoside monophosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • 6-oxopurine
  • Hypoxanthine
  • Monosaccharide phosphate
  • Pentose monosaccharide
  • Purinone
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Pyrimidone
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Pyrimidine
  • Tetrahydrofuran
  • Azole
  • Vinylogous amide
  • Imidazole
  • Heteroaromatic compound
  • Secondary alcohol
  • Urea
  • Lactam
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Alcohol
  • Organonitrogen compound
  • Organooxygen compound
  • Organic anion
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-4ChemAxon
pKa (Strongest Acidic)0.9ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area320.65 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity102.54 m³·mol⁻¹ChemAxon
Polarizability38.63 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Emam EAF, Roy K, Varshney U: An exchange of single amino acid between the phosphohydrolase modules of Escherichia coli MutT and Mycobacterium smegmatis MutT1 switches their cleavage specificities. DNA Repair (Amst). 2024 Jul;139:103693. doi: 10.1016/j.dnarep.2024.103693. Epub 2024 May 15. [PubMed:38776712 ]
  2. Li Y, Wang X: The role of DNA and RNA guanosine oxidation in cardiovascular diseases. Pharmacol Res. 2024 Jun;204:107187. doi: 10.1016/j.phrs.2024.107187. Epub 2024 Apr 23. [PubMed:38657843 ]
  3. Nigo F, Nakagawa R, Hirai Y, Imai L, Suzuki Y, Furuta K, Kaito C: Staphylococcus aureus MazG hydrolyzes oxidized guanine nucleotides and contributes to oxidative stress resistance. Biochimie. 2023 Jun;209:52-60. doi: 10.1016/j.biochi.2023.02.001. Epub 2023 Feb 4. [PubMed:36746255 ]
  4. Kondo Y, Rikiishi K, Sugimoto M: Rice Nudix Hydrolase OsNUDX2 Sanitizes Oxidized Nucleotides. Antioxidants (Basel). 2022 Sep 13;11(9):1805. doi: 10.3390/antiox11091805. [PubMed:36139879 ]
  5. Li J, Wang ZH, Dang YM, Li DN, Liu Z, Dai DP, Cai JP: MTH1 suppression enhances the stemness of MCF7 through upregulation of STAT3. Free Radic Biol Med. 2022 Aug 1;188:447-458. doi: 10.1016/j.freeradbiomed.2022.06.240. Epub 2022 Jul 6. [PubMed:35809767 ]
  6. Raj P, Karthik S, Arif SM, Varshney U, Vijayan M: Plasticity, ligand conformation and enzyme action of Mycobacterium smegmatis MutT1. Acta Crystallogr D Struct Biol. 2020 Oct 1;76(Pt 10):982-992. doi: 10.1107/S2059798320010992. Epub 2020 Sep 16. [PubMed:33021500 ]
  7. Samaan GN, Paranagama N, Haque A, Hecht DA, Swairjo MA, Purse BW: Structure-based design of guanosine analogue inhibitors targeting GTP cyclohydrolase IB towards a new class of antibiotics. Bioorg Med Chem Lett. 2020 Jan 15;30(2):126818. doi: 10.1016/j.bmcl.2019.126818. Epub 2019 Nov 12. [PubMed:31771800 ]
  8. Arif SM, Patil AG, Varshney U, Vijayan M: Biochemical and structural studies of Mycobacterium smegmatis MutT1, a sanitization enzyme with unusual modes of association. Acta Crystallogr D Struct Biol. 2017 Apr 1;73(Pt 4):349-364. doi: 10.1107/S2059798317002534. Epub 2017 Mar 31. [PubMed:28375146 ]
  9. Paranagama N, Bonnett SA, Alvarez J, Luthra A, Stec B, Gustafson A, Iwata-Reuyl D, Swairjo MA: Mechanism and catalytic strategy of the prokaryotic-specific GTP cyclohydrolase-IB. Biochem J. 2017 Mar 7;474(6):1017-1039. doi: 10.1042/BCJ20161025. [PubMed:28126741 ]
  10. Tanaka S, Kihara M, Sugimoto M: Structure and molecular characterization of barley nudix hydrolase genes. Biosci Biotechnol Biochem. 2015;79(3):394-401. doi: 10.1080/09168451.2014.978259. Epub 2014 Nov 7. [PubMed:25379607 ]
  11. Gordon AJ, Satory D, Wang M, Halliday JA, Golding I, Herman C: Removal of 8-oxo-GTP by MutT hydrolase is not a major contributor to transcriptional fidelity. Nucleic Acids Res. 2014 Oct 29;42(19):12015-26. doi: 10.1093/nar/gku912. Epub 2014 Oct 7. [PubMed:25294823 ]
  12. Kumpornsin K, Kotanan N, Chobson P, Kochakarn T, Jirawatcharadech P, Jaru-ampornpan P, Yuthavong Y, Chookajorn T: Biochemical and functional characterization of Plasmodium falciparum GTP cyclohydrolase I. Malar J. 2014 Apr 19;13:150. doi: 10.1186/1475-2875-13-150. [PubMed:24745605 ]
  13. Patil AG, Sang PB, Govindan A, Varshney U: Mycobacterium tuberculosis MutT1 (Rv2985) and ADPRase (Rv1700) proteins constitute a two-stage mechanism of 8-oxo-dGTP and 8-oxo-GTP detoxification and adenosine to cytidine mutation avoidance. J Biol Chem. 2013 Apr 19;288(16):11252-62. doi: 10.1074/jbc.M112.442566. Epub 2013 Mar 5. [PubMed:23463507 ]
  14. Sekiguchi T, Ito R, Hayakawa H, Sekiguchi M: Elimination and utilization of oxidized guanine nucleotides in the synthesis of RNA and its precursors. J Biol Chem. 2013 Mar 22;288(12):8128-8135. doi: 10.1074/jbc.M112.418723. Epub 2013 Feb 3. [PubMed:23376345 ]
  15. Sang PB, Varshney U: Biochemical properties of MutT2 proteins from Mycobacterium tuberculosis and M. smegmatis and their contrasting antimutator roles in Escherichia coli. J Bacteriol. 2013 Apr;195(7):1552-60. doi: 10.1128/JB.02102-12. Epub 2013 Jan 25. [PubMed:23354752 ]