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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-12 23:20:46 UTC
Update Date2021-09-14 15:40:09 UTC
HMDB IDHMDB0003537
Secondary Accession Numbers
  • HMDB03537
Metabolite Identification
Common Name2'-Deoxyinosine triphosphate
Description2'-Deoxyinosine triphosphate (dITP) is a deoxyribonucleotide that may be generated from dATP by slow, non-enzymatic hydrolysis or by reduction of ITP. Normally, the cellular dITP concentration is very low. The inability to demonstrate the synthesis of dITP in cellular preparations has been attributed to the presence in the cytoplasm of an inosine triphosphatase pyrophosphatase (ITPase, EC 3.6.1.19), an enzyme that does not permit accumulation of these nucleotides. dITP can be incorporated into DNA by polymerases. The deoxyribonucleotide dITP behaves as a dGTP analogue and is incorporated opposite cytosine with about 50% efficiency. Both isolated nuclei and purified DNA polymerases rapidly incorporated dITP into DNA. In the presence of ATP, dITP is stabilized in extracts of nuclei. dITP exist in all cells and is potentially mutagenic, and the levels of these nucleotides are controlled by ITPase. The function of this ubiquitous protein family is proposed to be the elimination of minor potentially mutagenic or clastogenic purine nucleoside triphosphates from the cell. (PMID: 11278832 ).
Structure
Data?1582752280
Synonyms
ValueSource
2'-Deoxyinosine 5'-triphosphateChEBI
2'-Deoxyinosine-5'-triphosphateChEBI
Deoxyinosine 5'-triphosphateChEBI
2'-Deoxyinosine 5'-triphosphoric acidGenerator
2'-Deoxyinosine-5'-triphosphoric acidGenerator
Deoxyinosine 5'-triphosphoric acidGenerator
2'-Deoxyinosine triphosphoric acidGenerator
2'-Deoxy-inosine 5'-(tetrahydrogen triphosphate)HMDB
2'-DitpHMDB
Deoxyinosine triphosphateHMDB
DITPHMDB
2'-Deoxyinosine triphosphate, trisodium saltHMDB
2'-Deoxyinosine triphosphateMeSH
Chemical FormulaC10H15N4O13P3
Average Molecular Weight492.1664
Monoisotopic Molecular Weight491.984846122
IUPAC Name{[hydroxy({[hydroxy({[(2R,3S,5R)-3-hydroxy-5-(6-oxo-6,9-dihydro-3H-purin-9-yl)oxolan-2-yl]methoxy})phosphoryl]oxy})phosphoryl]oxy}phosphonic acid
Traditional Name[hydroxy({hydroxy[(2R,3S,5R)-3-hydroxy-5-(6-oxo-3H-purin-9-yl)oxolan-2-yl]methoxyphosphoryl}oxy)phosphoryl]oxyphosphonic acid
CAS Registry Number16595-02-1
SMILES
O[C@H]1C[C@@H](O[C@@H]1COP(O)(=O)OP(O)(=O)OP(O)(O)=O)N1C=NC2=C1NC=NC2=O
InChI Identifier
InChI=1S/C10H15N4O13P3/c15-5-1-7(14-4-13-8-9(14)11-3-12-10(8)16)25-6(5)2-24-29(20,21)27-30(22,23)26-28(17,18)19/h3-7,15H,1-2H2,(H,20,21)(H,22,23)(H,11,12,16)(H2,17,18,19)/t5-,6+,7+/m0/s1
InChI KeyUFJPAQSLHAGEBL-RRKCRQDMSA-N
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.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine deoxyribonucleotides
Direct ParentPurine 2'-deoxyribonucleoside triphosphates
Alternative Parents
Substituents
  • Purine 2'-deoxyribonucleoside triphosphate
  • 6-oxopurine
  • Hypoxanthine
  • Imidazopyrimidine
  • Purine
  • Pyrimidone
  • Monoalkyl phosphate
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Pyrimidine
  • Alkyl phosphate
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Azole
  • Vinylogous amide
  • Imidazole
  • Secondary alcohol
  • Azacycle
  • Organoheterocyclic compound
  • Oxacycle
  • Hydrocarbon derivative
  • Alcohol
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-3.355Not Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility5.04 g/LALOGPS
logP10(-0.26) g/LALOGPS
logP10(-3.8) g/LChemAxon
logS10(-2) g/LALOGPS
pKa (Strongest Acidic)0.89ChemAxon
pKa (Strongest Basic)2.85ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area248.56 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity92.01 m³·mol⁻¹ChemAxon
Polarizability36.03 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+201.51931661259
DarkChem[M-H]-195.54831661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2'-Deoxyinosine triphosphate,1TMS,#1C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2[NH]C=NC3=O)O[C@@H]1COP(=O)(O)OP(=O)(O)OP(=O)(O)O3755.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
2'-Deoxyinosine triphosphate,1TMS,#2C[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C2[NH]C=NC3=O)C[C@@H]1O)OP(=O)(O)OP(=O)(O)O3800.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
2'-Deoxyinosine triphosphate,1TMS,#3C[Si](C)(C)OP(=O)(OP(=O)(O)O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C2[NH]C=NC3=O)C[C@@H]1O3807.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
2'-Deoxyinosine triphosphate,1TMS,#4C[Si](C)(C)OP(=O)(O)OP(=O)(O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C2[NH]C=NC3=O)C[C@@H]1O3775.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
2'-Deoxyinosine triphosphate,1TMS,#5C[Si](C)(C)N1C=NC(=O)C2=C1N([C@H]1C[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O1)C=N23832.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
2'-Deoxyinosine triphosphate,1TBDMS,#1CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2[NH]C=NC3=O)O[C@@H]1COP(=O)(O)OP(=O)(O)OP(=O)(O)O3963.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
2'-Deoxyinosine triphosphate,1TBDMS,#2CC(C)(C)[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C2[NH]C=NC3=O)C[C@@H]1O)OP(=O)(O)OP(=O)(O)O4018.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
2'-Deoxyinosine triphosphate,1TBDMS,#3CC(C)(C)[Si](C)(C)OP(=O)(OP(=O)(O)O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C2[NH]C=NC3=O)C[C@@H]1O4023.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
2'-Deoxyinosine triphosphate,1TBDMS,#4CC(C)(C)[Si](C)(C)OP(=O)(O)OP(=O)(O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C2[NH]C=NC3=O)C[C@@H]1O4005.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
2'-Deoxyinosine triphosphate,1TBDMS,#5CC(C)(C)[Si](C)(C)N1C=NC(=O)C2=C1N([C@H]1C[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O1)C=N24094.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2'-Deoxyinosine triphosphate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0c2a-9783500000-aa0125a217188c7947c62017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2'-Deoxyinosine triphosphate GC-MS (1 TMS) - 70eV, Positivesplash10-0002-9461120000-3124f5b05f1627f4eec92017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2'-Deoxyinosine triphosphate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2'-Deoxyinosine triphosphate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Deoxyinosine triphosphate 10V, Positive-QTOFsplash10-000i-0901200000-094550daf6257cf48e862015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Deoxyinosine triphosphate 20V, Positive-QTOFsplash10-000i-0900000000-7da6dbb92e894a102ada2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Deoxyinosine triphosphate 40V, Positive-QTOFsplash10-000i-1910000000-297ae75d9d85a395a0192015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Deoxyinosine triphosphate 10V, Negative-QTOFsplash10-0006-0220900000-05764a0399ea663bda0a2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Deoxyinosine triphosphate 20V, Negative-QTOFsplash10-002r-7940100000-7be6289aa2147474bbc82015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Deoxyinosine triphosphate 40V, Negative-QTOFsplash10-056r-9710000000-4a8af53537c11f3268fe2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Deoxyinosine triphosphate 10V, Negative-QTOFsplash10-0006-0001900000-782c2e9109d8585c1eec2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Deoxyinosine triphosphate 20V, Negative-QTOFsplash10-004l-7613900000-af9cb037c1346339427b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Deoxyinosine triphosphate 40V, Negative-QTOFsplash10-004i-9101000000-04cea8b7d7b629572e4b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Deoxyinosine triphosphate 10V, Positive-QTOFsplash10-000i-0900000000-b2e36fb98660834d7d242021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Deoxyinosine triphosphate 20V, Positive-QTOFsplash10-000i-0900000000-b2e36fb98660834d7d242021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Deoxyinosine triphosphate 40V, Positive-QTOFsplash10-000i-0921000000-baeff84496f2b6c02a0a2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023190
KNApSAcK IDNot Available
Chemspider ID129052
KEGG Compound IDC01345
BioCyc IDNot Available
BiGG ID37399
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound146302
PDB IDNot Available
ChEBI ID28807
Food Biomarker OntologyNot Available
VMH IDDITP
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Lin S, McLennan AG, Ying K, Wang Z, Gu S, Jin H, Wu C, Liu W, Yuan Y, Tang R, Xie Y, Mao Y: Cloning, expression, and characterization of a human inosine triphosphate pyrophosphatase encoded by the itpa gene. J Biol Chem. 2001 Jun 1;276(22):18695-701. Epub 2001 Mar 13. [PubMed:11278832 ]

Enzymes

General function:
Involved in nucleoside diphosphate kinase activity
Specific function:
Major role in the synthesis of nucleoside triphosphates other than ATP (By similarity).
Gene Name:
NME4
Uniprot ID:
O00746
Molecular weight:
20658.45
Reactions
Adenosine triphosphate + dIDP → ADP + 2'-Deoxyinosine triphosphatedetails
General function:
Involved in nucleoside diphosphate kinase activity
Specific function:
Major role in the synthesis of nucleoside triphosphates other than ATP. Possesses nucleoside-diphosphate kinase, serine/threonine-specific protein kinase, geranyl and farnesyl pyrophosphate kinase, histidine protein kinase and 3'-5' exonuclease activities. Involved in cell proliferation, differentiation and development, signal transduction, G protein-coupled receptor endocytosis, and gene expression. Required for neural development including neural patterning and cell fate determination.
Gene Name:
NME1
Uniprot ID:
P15531
Molecular weight:
17148.635
Reactions
Adenosine triphosphate + dIDP → ADP + 2'-Deoxyinosine triphosphatedetails
General function:
Involved in nucleoside diphosphate kinase activity
Specific function:
Major role in the synthesis of nucleoside triphosphates other than ATP. The ATP gamma phosphate is transferred to the NDP beta phosphate via a ping-pong mechanism, using a phosphorylated active-site intermediate.
Gene Name:
NME7
Uniprot ID:
Q9Y5B8
Molecular weight:
42491.365
Reactions
Adenosine triphosphate + dIDP → ADP + 2'-Deoxyinosine triphosphatedetails
General function:
Involved in nucleoside diphosphate kinase activity
Specific function:
Major role in the synthesis of nucleoside triphosphates other than ATP. Negatively regulates Rho activity by interacting with AKAP13/LBC. Acts as a transcriptional activator of the MYC gene; binds DNA non-specifically (PubMed:8392752). Exhibits histidine protein kinase activity.
Gene Name:
NME2
Uniprot ID:
P22392
Molecular weight:
30136.92
Reactions
Adenosine triphosphate + dIDP → ADP + 2'-Deoxyinosine triphosphatedetails
General function:
Involved in nucleoside diphosphate kinase activity
Specific function:
Major role in the synthesis of nucleoside triphosphates other than ATP. The ATP gamma phosphate is transferred to the NDP beta phosphate via a ping-pong mechanism, using a phosphorylated active-site intermediate. Probably has a role in normal hematopoiesis by inhibition of granulocyte differentiation and induction of apoptosis.
Gene Name:
NME3
Uniprot ID:
Q13232
Molecular weight:
19014.85
Reactions
Adenosine triphosphate + dIDP → ADP + 2'-Deoxyinosine triphosphatedetails
General function:
Involved in nucleoside diphosphate kinase activity
Specific function:
Major role in the synthesis of nucleoside triphosphates other than ATP. The ATP gamma phosphate is transferred to the NDP beta phosphate via a ping-pong mechanism, using a phosphorylated active-site intermediate. Inhibitor of p53-induced apoptosis.
Gene Name:
NME6
Uniprot ID:
O75414
Molecular weight:
22002.965
Reactions
Adenosine triphosphate + dIDP → ADP + 2'-Deoxyinosine triphosphatedetails
General function:
Involved in hydrolase activity
Specific function:
Pyrophosphatase that hydrolyzes the non-canonical purine nucleotides inosine triphosphate (ITP), deoxyinosine triphosphate (dITP) as well as 2'-deoxy-N-6-hydroxylaminopurine triposphate (dHAPTP) and xanthosine 5'-triphosphate (XTP) to their respective monophosphate derivatives. The enzyme does not distinguish between the deoxy- and ribose forms. Probably excludes non-canonical purines from RNA and DNA precursor pools, thus preventing their incorporation into RNA and DNA and avoiding chromosomal lesions.
Gene Name:
ITPA
Uniprot ID:
Q9BY32
Molecular weight:
16833.23
Reactions
2'-Deoxyinosine triphosphate + Water → dIMP + Pyrophosphatedetails
General function:
Not Available
Specific function:
Does not seem to have NDK kinase activity. Confers protection from cell death by Bax and alters the cellular levels of several antioxidant enzymes including Gpx5. May play a role in spermiogenesis by increasing the ability of late-stage spermatids to eliminate reactive oxygen species (By similarity).
Gene Name:
NME5
Uniprot ID:
P56597
Molecular weight:
Not Available
Reactions
Adenosine triphosphate + dIDP → ADP + 2'-Deoxyinosine triphosphatedetails