Human Metabolome Database Version 3.5

Showing metabocard for dGTP (HMDB01440)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-29 13:31:39 -0600
HMDB ID HMDB01440
Secondary Accession Numbers None
Metabolite Identification
Common Name dGTP
Description Under normal physiologic conditions, deoxyguanosine (dGuo) undergoes phosphorolysis by purine nucleoside phosphorylase (PNP, EC 2.4.2.1, an enzyme involved in the recycling of nucleosides and deoxynucleosides in cellular remodeling). However, when PNP is inhibited, deoxycytidine kinase (dCK, EC 2.7.1.74) shunts unmetabolized dGuo into deoxyguanosine triphosphate (dGTP), which accumulates and blocks DNA synthesis. Deficiency of purine nucleoside phosphorylase results in defective T-cell immunity. A correlation between the degree of T cell inhibition and the level of dCK activity is observed. (PMID: 11287638 Link_out, 402573 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Deoxyguanosine 5'-triphosphate
  2. 2'-Deoxyguanosine 5'-triphosphate
  3. 2'-Deoxyguanosine triphosphate
  4. Deoxyguanosine triphosphate
Chemical Formula C10H16N5O13P3
Average Molecular Weight 507.181
Monoisotopic Molecular Weight 506.995745159
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 ({[(2R,3S,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxyphosphonic acid
CAS Registry Number 2564-35-4
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
InChI Identifier 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
InChI Key HAAZLUGHYHWQIW-KVQBGUIXSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Nucleosides, Nucleotides, and Analogues
Class Purine Nucleotides
Sub Class Purine Deoxyribonucleotides
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • Deoxyribonucleotides(KEGG)
  • Organic Compounds
  • deoxyguanosine phosphate(ChEBI)
  • purine 2'-deoxyribonucleoside 5'-triphosphate(ChEBI)
Substituents
  • Aminopyrimidine
  • Hypoxanthine
  • Imidazole
  • Imidazopyrimidine
  • Organic Hypophosphite
  • Organic Phosphite
  • Organic Pyrophosphate
  • Oxolane
  • Phosphoric Acid Ester
  • Purine
  • Purinone
  • Pyrimidine
  • Pyrimidone
  • Secondary Alcohol
Direct Parent Purine 2'-deoxyribonucleoside Triphosphates
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction
  • DNA component
Application Not Available
Cellular locations
  • Mitochondria
  • Nucleus
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 5.59 g/L ALOGPS
LogP -0.61 ALOGPS
LogP -2.8 ChemAxon
LogS -1.96 ALOGPS
pKa (strongest acidic) 0.82 ChemAxon
pKa (strongest basic) 1.61 ChemAxon
Hydrogen Acceptor Count 13 ChemAxon
Hydrogen Donor Count 7 ChemAxon
Polar Surface Area 274.58 A2 ChemAxon
Rotatable Bond Count 8 ChemAxon
Refractivity 95.73 ChemAxon
Polarizability 39.1 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -3 ChemAxon
Spectra
1H NMR Spectrum
[1H,1H] 2D NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Mitochondria
  • Nucleus
Biofluid Locations Not Available
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Purine Metabolism SMP00050 map00230 Link_out
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022623
KNApSAcK ID Not Available
Chemspider ID 58613 Link_out
KEGG Compound ID C00286 Link_out
BioCyc ID DGTP Link_out
BiGG ID 34502 Link_out
Wikipedia Link Deoxyguanosine triphosphate Link_out
NuGOwiki Link HMDB01440 Link_out
Metagene Link HMDB01440 Link_out
METLIN ID 6248 Link_out
PubChem Compound 65103 Link_out
PDB ID DGT Link_out
ChEBI ID 16497 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. 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 Link_out
  2. 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 Link_out

Enzymes
Name: Uridine-cytidine kinase 1
Reactions:
dGTP + Uridine unknown dGDP + Uridine 5'-monophosphate details
dGTP + Cytidine unknown dGDP + Cytidine monophosphate details
Gene Name: UCK1
Uniprot ID: Q9HA47 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Nucleoside diphosphate kinase, mitochondrial
Reactions:
Adenosine triphosphate + dGDP unknown ADP + dGTP details
Gene Name: NME4
Uniprot ID: O00746 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Nucleoside diphosphate kinase A
Reactions:
Adenosine triphosphate + dGDP unknown ADP + dGTP details
Gene Name: NME1
Uniprot ID: P15531 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Nucleoside diphosphate kinase 7
Reactions:
Adenosine triphosphate + dGDP unknown ADP + dGTP details
Gene Name: NME7
Uniprot ID: Q9Y5B8 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Nucleoside diphosphate kinase B
Reactions:
Adenosine triphosphate + dGDP unknown ADP + dGTP details
Gene Name: NME2
Uniprot ID: P22392 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Nucleoside diphosphate kinase 3
Reactions:
Adenosine triphosphate + dGDP unknown ADP + dGTP details
Gene Name: NME3
Uniprot ID: Q13232 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Nucleoside diphosphate kinase 6
Reactions:
Adenosine triphosphate + dGDP unknown ADP + dGTP details
Gene Name: NME6
Uniprot ID: O75414 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Inosine triphosphate pyrophosphatase
Reactions:
dGTP + Water unknown 2'-Deoxyguanosine 5'-monophosphate + Pyrophosphate details
Gene Name: ITPA
Uniprot ID: Q9BY32 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Pyruvate kinase isozymes M1/M2
Reactions:
dGTP + Pyruvic acid unknown dGDP + Phosphoenolpyruvic acid details
Gene Name: PKM
Uniprot ID: P14618 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Pyruvate kinase isozymes R/L
Reactions:
dGTP + Pyruvic acid unknown dGDP + Phosphoenolpyruvic acid details
Gene Name: PKLR
Uniprot ID: P30613 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: DNA polymerase beta
Reactions: Not Available
Gene Name: POLB
Uniprot ID: P06746 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: DNA polymerase alpha catalytic subunit
Reactions:
dGTP + DNA unknown Pyrophosphate + DNA details
Gene Name: POLA1
Uniprot ID: P09884 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: DNA polymerase delta subunit 3
Reactions: Not Available
Gene Name: POLD3
Uniprot ID: Q15054 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: DNA polymerase lambda
Reactions: Not Available
Gene Name: POLL
Uniprot ID: Q9UGP5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: DNA polymerase epsilon subunit 4
Reactions:
dGTP + DNA unknown Pyrophosphate + DNA details
Gene Name: POLE4
Uniprot ID: Q9NR33 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: DNA polymerase eta
Reactions: Not Available
Gene Name: POLH
Uniprot ID: Q9Y253 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: DNA polymerase delta catalytic subunit
Reactions:
dGTP + DNA unknown Pyrophosphate + DNA details
Gene Name: POLD1
Uniprot ID: P28340 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: DNA polymerase zeta catalytic subunit
Reactions: Not Available
Gene Name: REV3L
Uniprot ID: O60673 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: DNA polymerase epsilon catalytic subunit A
Reactions:
dGTP + DNA unknown Pyrophosphate + DNA details
Gene Name: POLE
Uniprot ID: Q07864 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: DNA-directed DNA/RNA polymerase mu
Reactions: Not Available
Gene Name: POLM
Uniprot ID: Q9NP87 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: DNA polymerase kappa
Reactions: Not Available
Gene Name: POLK
Uniprot ID: Q9UBT6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: DNA polymerase epsilon subunit 3
Reactions:
dGTP + DNA unknown Pyrophosphate + DNA details
Gene Name: POLE3
Uniprot ID: Q9NRF9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: DNA polymerase subunit gamma-1
Reactions: Not Available
Gene Name: POLG
Uniprot ID: P54098 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: DNA polymerase iota
Reactions: Not Available
Gene Name: POLI
Uniprot ID: Q9UNA4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: DNA polymerase epsilon subunit 2
Reactions:
dGTP + DNA unknown Pyrophosphate + DNA details
Gene Name: POLE2
Uniprot ID: P56282 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Uridine-cytidine kinase 2
Reactions:
dGTP + Uridine unknown dGDP + Uridine 5'-monophosphate details
dGTP + Cytidine unknown dGDP + Cytidine monophosphate details
Gene Name: UCK2
Uniprot ID: Q9BZX2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Uridine-cytidine kinase-like 1
Reactions:
dGTP + Uridine unknown dGDP + Uridine 5'-monophosphate details
dGTP + Cytidine unknown dGDP + Cytidine monophosphate details
Gene Name: UCKL1
Uniprot ID: Q9NWZ5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Myb-binding protein 1A
Reactions: Not Available
Gene Name: MYBBP1A
Uniprot ID: Q9BQG0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: DNA polymerase theta
Reactions: Not Available
Gene Name: POLQ
Uniprot ID: O75417 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: DNA polymerase delta subunit 2
Reactions:
dGTP + DNA unknown Pyrophosphate + DNA details
Gene Name: POLD2
Uniprot ID: P49005 Link_out
Protein Sequence: FASTA
Name: Nucleoside diphosphate kinase homolog 5
Reactions:
Adenosine triphosphate + dGDP unknown ADP + dGTP details
Gene Name: NME5
Uniprot ID: P56597 Link_out
Name: DNA primase small subunit
Reactions:
dGTP + DNA unknown Pyrophosphate + DNA details
Gene Name: PRIM1
Uniprot ID: P49642 Link_out
Name: DNA primase large subunit
Reactions:
dGTP + DNA unknown Pyrophosphate + DNA details
Gene Name: PRIM2
Uniprot ID: P49643 Link_out