8-Oxo-dGTP (YMDB00211)

Identification

YMDB ID

YMDB00211

Name

8-Oxo-dGTP

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

8-Oxo-dGTP 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. Based on a literature review very few articles have been published on 8-Oxo-dGTP.

Structure

MOL SDF PDB SMILES InChI

Synonyms

2'-deoxy-7,8-dihydro-8-oxo-Guanosine 5'-(tetrahydrogen triphosphate)
8-Hydroxy-2'-deoxyguanosine 5'-triphosphate
8-Oxo-2'-deoxyguanosine 5'-triphosphate
8-Oxo-7,8-dihydro-2'-deoxyguanosine 5'-triphosphate
8-Oxo-deoxyguanosine triphosphate
8-Oxo-dGTP
8-OH-dGTP
8-Hydroxy-dGTP
({[({[(3S)-5-(6,8-dihydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonate

CAS number

139307-94-1

Weight

Average: 523.1804
Monoisotopic: 522.990659781

InChI Key

BUZOGVVQWCXXDP-KLFYCJEISA-N

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)/t3-,4?,5?/m0/s1

IUPAC Name

({[({[(3S)-5-(2-amino-6,8-dioxo-6,7,8,9-tetrahydro-3H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid

Traditional IUPAC Name

({[(3S)-5-(2-amino-6,8-dioxo-3,7-dihydropurin-9-yl)-3-hydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxyphosphonic acid

Chemical Formula

C₁₀H₁₆N₅O₁₄P₃

SMILES

[H]O[C@@]1([H])C([H])([H])C([H])(OC1([H])C([H])([H])OP(=O)(O[H])OP(=O)(O[H])OP(=O)(O[H])O[H])N1C(=O)N([H])C2=C1N([H])C(=NC2=O)N([H])[H]

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.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleotides

Sub Class

Purine deoxyribonucleotides

Direct Parent

Purine 2'-deoxyribonucleoside triphosphates

Alternative Parents

Substituents

Purine 2'-deoxyribonucleoside triphosphate
6-oxopurine
Hypoxanthine
Purinone
Imidazopyrimidine
Purine
Aminopyrimidine
Monoalkyl phosphate
Pyrimidone
N-substituted imidazole
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Pyrimidine
Heteroaromatic compound
Azole
Imidazole
Vinylogous amide
Tetrahydrofuran
Urea
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Azacycle
Organopnictogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Amine
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Solid

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	10.3 g/L	ALOGPS
logP	-0.38	ALOGPS
logP	-4.5	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	0.99	ChemAxon
pKa (Strongest Basic)	2.59	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	289.1 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	105.31 m³·mol⁻¹	ChemAxon
Polarizability	39.75 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Nucleus, Peroxisome

Organoleptic Properties

Not Available

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-054n-9573110000-daaf44eb7513200301d5	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-03kc-7239120000-fb89512d66b2c0c73399	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-36f2c770086e2025286f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0900000000-abb035705d7ecec8a5ce	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gb9-0900000000-69efc100442e712d235b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0330390000-a2ee834d8adc4368c864	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-057u-6960010000-f32163c3a928e66f90da	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9300000000-8dfeadd910412236d96f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0200190000-b3c0c051edf4db2e79dc	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9200000000-5e99ccfb36b7eed2abad	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9100000000-f5f1ce37066a191803dc	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0000090000-13566b7f77951efcb4cf	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0934120000-ff6ec74209f0a1126fa2	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0300-0591000000-b017e508ae33ab810f1d	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer

References

References:

UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	Not Available
HMDB ID	HMDB11615
Pubchem Compound ID	107902
Kegg ID	Not Available
ChemSpider ID	24784983
FOODB ID	FDB028320
Wikipedia ID	Not Available
BioCyc ID	Not Available

Enzymes

Protein Details

1. Peroxisomal coenzyme A diphosphatase 1, peroxisomal

General function:: Involved in hydrolase activity
Specific function:: Coenzyme A diphosphatase which mediates the cleavage of CoA into 3',5'-ADP and 4'-phosphopantetheine. Has a strong preference for oxidized CoA disulfide (CoASSCoA) as substrate. May be required to remove potentially toxic oxidized CoA disulfide to maintain the capacity for beta-oxidation of fatty acids. Can degrade 8-oxo-dGTP in vitro; however, such activity may not be relevant in vivo
Gene Name:: PCD1
Uniprot ID:: Q12524
Molecular weight:: 39754.5

Reactions

8-oxo-dGTP + H(2)O → 8-oxo-dGMP + diphosphate.

Structure for #<Compound:0x037f0f8c>

Enzymes

Reactions