P. aeruginosa Metabolome Database: dGTP (PAMDB000389)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB000389

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

🔍MOL SDF PDB SMILES InChI View Structure

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

Average Molecular Weight:

507.181

Monoisotopic Molecular Weight:

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

Taxonomy Description

This compound 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
Organic pyrophosphate
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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

deoxyguanosine phosphate (CHEBI:16497 )
guanyl deoxyribonucleotide (CHEBI:16497 )
purine 2'-deoxyribonucleoside 5'-triphosphate (CHEBI:16497 )
Deoxyribonucleotides (C00286 )

Physical Properties

State:

Solid

Charge:

-3

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	5.59 mg/mL	ALOGPS
logP	-0.61	ALOGPS
logP	-2.8	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	1.61	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	274.58 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	95.73 m³·mol^-1	ChemAxon
Polarizability	39.1 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:

Cytoplasm

Reactions:

2 Flavodoxin reduced + Guanosine triphosphate + 2 Hydrogen ion > dGTP +2 flavodoxin semi oxidized + Water
dGTP + Water > 2'-Deoxyguanosine 5'-monophosphate + Hydrogen ion + Pyrophosphate
Adenosine triphosphate + dGDP <> ADP + dGTP
dGTP + Water <> Deoxyguanosine + Triphosphate
dGTP + DNA <> Pyrophosphate + DNA
dGTP + Water <> 2'-Deoxyguanosine 5'-monophosphate + Pyrophosphate
Adenosine triphosphate + dGDP <> ADP + dGTP
dGTP + Pyruvic acid <> dGDP + Phosphoenolpyruvic acid
dGTP + Uridine <> dGDP + Uridine 5'-monophosphate
dGTP + Thioredoxin disulfide + Water <> Guanosine triphosphate + Thioredoxin
dGTP + Cytidine <> dGDP + Cytidine monophosphate
dGTP + hydroxyl radical > Hydrogen ion + 8-oxo-dGTP
Water + dGTP > Hydrogen ion + Triphosphate + Deoxyguanosine
dGDP + Adenosine triphosphate + dGDP > Adenosine diphosphate + dGTP + ADP
Guanosine triphosphate + a reduced flavodoxin > dGTP + an oxidized flavodoxin + Water

Pathways:

Purine metabolism pae00230
Pyrimidine metabolism pae00240

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0910100000-0b4a31d8c636c368a5ae	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0900000000-1158073094ef9de8ec75	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-0900000000-4330d672c10b6546947e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0330290000-f951ce7240e0b3c9bb63	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fb9-7940100000-9f33838fecee36769f00	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-056r-9710000000-e1ba8d1db7700c321064	View in MoNA
1D NMR	1H NMR Spectrum	Not Available
1D NMR	1H NMR Spectrum	Not Available
1D NMR	13C NMR Spectrum	Not Available
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available
2D NMR	[1H,13C] 2D NMR Spectrum	Not 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)

Links

External Links:

Resource	Link
CHEBI ID	16497
HMDB ID	HMDB01440
Pubchem Compound ID	65103
Kegg ID	C00286
ChemSpider ID	58613
Wikipedia	Deoxyguanosine triphosphate
BioCyc ID	DGTP
EcoCyc ID	DGTP
Ligand Expo	DGT

dGTP (PAMDB000389)

Structure for dGTP (PAMDB000389)