CHEBI:16497 - dGTP

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ChEBI Name dGTP
ChEBI ID CHEBI:16497
Definition A purine 2'-deoxyribonucleoside 5'-triphosphate having guanine as the nucleobase.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:10497, CHEBI:19247, CHEBI:14076
Supplier Information ChemicalBook:CB7266885, eMolecules:5747847, ZINC000008215755
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Deoxyguanosine triphosphate (dGTP) is a nucleoside triphosphate, and a nucleotide precursor used in cells for DNA synthesis. The substance is used in the polymerase chain reaction technique, in sequencing, and in cloning. It is also the competitor of inhibition onset by acyclovir in the treatment of HSV virus.
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Formula C10H16N5O13P3
Net Charge 0
Average Mass 507.181
Monoisotopic Mass 506.99575
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
InChIKey HAAZLUGHYHWQIW-KVQBGUIXSA-N
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
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Mus musculus (NCBI:txid10090) From MetaboLights See: MetaboLights Study
Arabidopsis thaliana (NCBI:txid3702) From MetaboLights See: MetaboLights Study
Solanum lycopersicum (NCBI:txid4081) Found in leaf (BTO:0000713). From MetaboLights See: MetaboLights Study
Saccharomyces cerevisiae (NCBI:txid4932) See: PubMed
Escherichia coli (NCBI:txid562) See: PubMed
Homo sapiens (NCBI:txid9606) See: DOI
Roles Classification
Biological Role(s): Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
Saccharomyces cerevisiae metabolite
Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ).
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
(via nucleoside 5'-triphoshate )
Arabidopsis thaliana metabolite
Any plant metabolite that is produced by Arabidopsis thaliana.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing dGTP (CHEBI:16497) has role Arabidopsis thaliana metabolite (CHEBI:140602)
dGTP (CHEBI:16497) has role Escherichia coli metabolite (CHEBI:76971)
dGTP (CHEBI:16497) has role Saccharomyces cerevisiae metabolite (CHEBI:75772)
dGTP (CHEBI:16497) has role human metabolite (CHEBI:77746)
dGTP (CHEBI:16497) has role mouse metabolite (CHEBI:75771)
dGTP (CHEBI:16497) has role plant metabolite (CHEBI:76924)
dGTP (CHEBI:16497) is a deoxyguanosine phosphate (CHEBI:23625)
dGTP (CHEBI:16497) is a guanyl deoxyribonucleotide (CHEBI:63573)
dGTP (CHEBI:16497) is a purine 2'-deoxyribonucleoside 5'-triphosphate (CHEBI:37042)
dGTP (CHEBI:16497) is conjugate acid of dGTP(3−) (CHEBI:57794)
Incoming dGTP(3−) (CHEBI:57794) is conjugate base of dGTP (CHEBI:16497)
IUPAC Name
2'-deoxyguanosine 5'-(tetrahydrogen triphosphate)
Synonyms Sources
2'-deoxy-GTP ChEBI
2'-deoxyguanosine 5'-triphosphate KEGG COMPOUND
2'-deoxyguanosine triphosphate ChEBI
deoxy-GTP HMDB
deoxyguanosine 5'-triphosphate KEGG COMPOUND
deoxyguanosine triphosphate KEGG COMPOUND
dGTP KEGG COMPOUND
Manual Xrefs Databases
58613 ChemSpider
C00019346 KNApSAcK
C00286 KEGG COMPOUND
DB02181 DrugBank
Deoxyguanosine_triphosphate Wikipedia
DGT PDBeChem
ECMDB01440 ECMDB
FDB022623 FooDB
HMDB0001440 HMDB
YMDB00744 YMDB
View more database links
Registry Numbers Types Sources
2564-35-4 CAS Registry Number ChemIDplus
73481 Reaxys Registry Number Reaxys
Citations
Ji X, Wu Y, Yan J, Mehrens J, Yang H, DeLucia M, Hao C, Gronenborn AM, Skowronski J, Ahn J, Xiong Y (2013)
Mechanism of allosteric activation of SAMHD1 by dGTP.
Nature structural & molecular biology 20, 1304-1309 [PubMed:24141705]
[show Abstract]
Itsko M, Schaaper RM (2017)
Suppressors of dGTP Starvation in Escherichia coli.
Journal of bacteriology 199, e00142-17 [PubMed:28373271]
[show Abstract]
Torti A, Lossani A, Savi L, Focher F, Wright GE, Brown NC, Xu WC (2011)
Clostridium difficile DNA polymerase IIIC: basis for activity of antibacterial compounds.
Current enzyme inhibition 7, 147-153 [PubMed:22844265]
[show Abstract]
Hardy CD, Schultz CS, Collins K (2001)
Requirements for the dGTP-dependent repeat addition processivity of recombinant Tetrahymena telomerase.
The Journal of biological chemistry 276, 4863-4871 [PubMed:11096070]
[show Abstract]
Davenne T, Klintman J, Sharma S, Rigby RE, Blest HTW, Cursi C, Bridgeman A, Dadonaite B, De Keersmaecker K, Hillmen P, Chabes A, Schuh A, Rehwinkel J (2020)
SAMHD1 Limits the Efficacy of Forodesine in Leukemia by Protecting Cells against the Cytotoxicity of dGTP.
Cell reports 31, 107640 [PubMed:32402273]
[show Abstract]
Barnes CO, Wu Y, Song J, Lin G, Baxter EL, Brewster AS, Nagarajan V, Holmes A, Soltis SM, Sauter NK, Ahn J, Cohen AE, Calero G (2019)
The crystal structure of dGTPase reveals the molecular basis of dGTP selectivity.
Proceedings of the National Academy of Sciences of the United States of America 116, 9333-9339 [PubMed:31019074]
[show Abstract]
Muller EG (1994)
Deoxyribonucleotides are maintained at normal levels in a yeast thioredoxin mutant defective in DNA synthesis.
The Journal of biological chemistry 269, 24466-24471 [PubMed:7929110]
[show Abstract]
Sato A, Cory JG (1981)
Evaluation of combinations of drugs that inhibit Ehrlich tumor cell ribonucleotide reductase.
Cancer research 41, 1637-1641 [PubMed:6783298]
[show Abstract]
Kaczmarek P, Jezowska-Bojczuk M, Bal W, Kasprzak KS (2005)
Determination of the stability constants and oxidation susceptibility of nickel(II) complexes with 2'-deoxyguanosine 5'-triphosphate and L-histidine.
Journal of inorganic biochemistry 99, 737-746 [PubMed:15708794]
[show Abstract]
Last Modified
27 July 2021