Record Information
Version2.0
Creation Date2012-05-31 13:58:51 -0600
Update Date2015-09-17 15:41:17 -0600
Secondary Accession Numbers
  • ECMDB03379
Identification
Name:Triphosphate
DescriptionA triphosphate is a salt or ester containing three phosphate groups. It is the ionic form of triphosphoric acid, a condensed form of phosphoric acid. Triphosphate is an intermediate in the biosynthesis of Folate, the metabolism of purine, the metabolism of Porphyrin, the metabolism of Pyrimidine and the metabolism of Thiamine. The cleavage of the high energy triphosphate bonds in ATP (to ADP or AMP) is the central route of generating energy in cells.
Structure
Thumb
Synonyms:
  • Bis(tetraoxidophosphato)dioxidophosphate(5-)
  • Bis(tetraoxidophosphato)dioxidophosphoric acid(5-)
  • Catena-triphosphate
  • Catena-triphosphoric acid
  • Inorganic open chain tripolyphosphate
  • Inorganic open chain tripolyphosphoric acid
  • Inorganic triphosphate
  • Inorganic triphosphoric acid
  • P3,i
  • Triphoshate
  • Triphoshic acid
  • Triphoshorate
  • Triphoshoric acid
  • Triphosphate
  • Triphosphate(5-)
  • Triphosphoric acid
  • Triphosphoric acid(5-)
  • Tripolyphosphate
  • Tripolyphosphoric acid
Chemical Formula:O10P3
Weight:Average: 252.9153
Monoisotopic: 252.870430756
InChI Key:UNXRWKVEANCORM-UHFFFAOYSA-I
InChI:InChI=1S/H5O10P3/c1-11(2,3)9-13(7,8)10-12(4,5)6/h(H,7,8)(H2,1,2,3)(H2,4,5,6)/p-5
CAS number:14127-68-5
IUPAC Name:{[hydroxy(phosphonooxy)phosphoryl]oxy}phosphonic acid
Traditional IUPAC Name:tripolyphosphate
SMILES:[O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O
Chemical Taxonomy
Description belongs to the class of inorganic compounds known as non-metal phosphates. These are inorganic non-metallic compounds containing a phosphate as its largest oxoanion.
KingdomInorganic compounds
Super ClassHomogeneous non-metal compounds
ClassNon-metal oxoanionic compounds
Sub ClassNon-metal phosphates
Direct ParentNon-metal phosphates
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkNot Available
External DescriptorsNot Available
Physical Properties
State:Solid
Charge:-4
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
logP-1.9ChemAxon
pKa (Strongest Acidic)0.89ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area170.82 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity36.4 m³·mol⁻¹ChemAxon
Polarizability14.67 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Water + Triphosphate > Hydrogen ion + Phosphate + Pyrophosphate
Guanosine triphosphate + Water > Guanosine + Triphosphate
dGTP + Water <> Deoxyguanosine + Triphosphate
Adenosine triphosphate + Cob(I)alamin + Hydrogen ion <> Adenosylcobalamin + Triphosphate
Adenosine triphosphate + Cobinamide + Hydrogen ion <> Adenosyl cobinamide + Triphosphate
Adenosine triphosphate + Pyrophosphate <> ADP + Triphosphate
Dihydroneopterin triphosphate + Water > Acetaldehyde + 6-Carboxy-5,6,7,8-tetrahydropterin + Hydrogen ion + Triphosphate
Adenosine triphosphate + Cob(I)alamin <> Triphosphate + Adenosylcobalamin
Dihydroneopterin triphosphate <> Dyspropterin + Triphosphate
Cob(I)yrinate a,c diamide + Adenosine triphosphate <> Adenosyl cobyrinate a,c diamide + Triphosphate
Adenosine triphosphate + Cobinamide <> Triphosphate + Adenosyl cobinamide
Cob(I)yrinate a,c diamide + Adenosine triphosphate > Adenosyl cobinamide + Triphosphate
Adenosine triphosphate + Cob(I)alamin > Adenosylcobalamin + Triphosphate
Water + dGTP > Hydrogen ion + Triphosphate + Deoxyguanosine
Adenosine triphosphate + Cob(I)yrinate a,c diamide > Triphosphate + Adenosylcob(III)yrinic acid a,c-diamide
Adenosine triphosphate + Cobinamide > Triphosphate + Adenosyl cobinamide
dGTP + Water > Deoxyguanosine + Triphosphate
Dihydroneopterin triphosphate + Water > 6-Carboxy-5,6,7,8-tetrahydropterin + Acetaldehyde + Triphosphate
Adenosine triphosphate + Cob(I)yrinate a,c diamide + Cobinamide <> Triphosphate + Adenosyl cobyrinate a,c diamide + Adenosyl cobinamide
Triphosphate + Water <> Pyrophosphate + Phosphate
Cobinamide + Adenosine triphosphate + Cobinamide > Adenosyl cobinamide + Triphosphate + Adenosyl cobinamide + Triphosphate
Cobalamin + Adenosine triphosphate + vitamin B12 > coenzyme B12 + Triphosphate + Polyphosphate
Adenosine triphosphate + Cobalamin + vitamin B12 > Triphosphate + Adenosylcobalamin + Triphosphate
7,8-dihydroneopterin 3'-triphosphate + Water > Acetaldehyde + Triphosphate +2 Hydrogen ion + 6-Carboxy-5,6,7,8-tetrahydropterin + Triphosphate
dGTP + Water <> Deoxyguanosine + Triphosphate

SMPDB Pathways:
Folate biosynthesisPW000908 ThumbThumb?image type=greyscaleThumb?image type=simple
Oxidative phosphorylationPW000919 ThumbThumb?image type=greyscaleThumb?image type=simple
adenosylcobalamin salvage from cobinamidePW001884 ThumbThumb?image type=greyscaleThumb?image type=simple
preQ0 metabolismPW001893 ThumbThumb?image type=greyscaleThumb?image type=simple
purine nucleotides de novo biosynthesisPW000910 ThumbThumb?image type=greyscaleThumb?image type=simple
purine nucleotides de novo biosynthesis 2PW002033 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9520000000-e90a8c73374acf7bc122View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-2690000000-673654046903650b7152View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03fs-5930000000-5eb4974ca8fed7558024View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01qa-9500000000-b2404c5ea6e713839384View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-7ab59c02dffe21b7a604View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-9270000000-61dc72f8bf5e400f3882View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-6a7c993cb33cf4d5feddView in MoNA
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
Synthesis Reference:Tsuhako, Mitsutomo; Sueyoshi, Chiyoko; Miyajima, Tohru; Ohashi, Shigeru; Nariai, Hiroyuki; Motooka, Itaru. The reaction of cyclo-triphosphate with ethanolamines. Bulletin of the Chemical Society of Japan (1986), 59(10), 3091-5.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID18036
HMDB IDHMDB03379
Pubchem Compound ID3440921
Kegg IDC00536
ChemSpider ID2683694
WikipediaTriphosphoric_acid
BioCyc IDP3I
EcoCyc IDP3I
Ligand Expo3PO

Enzymes

General function:
Involved in catalytic activity
Specific function:
Catalyzes the reversible transfer of the terminal phosphate of ATP to form a long-chain polyphosphate (polyP). Can form linear polymers of orthophosphate with chain lengths up to 1000 or more. Can also act in the reverse direction to form ATP in the presence of excess ADP. Can also use GTP instead of ATP; but the efficiency of GTP is 5% that of ATP
Gene Name:
ppk
Uniprot ID:
P0A7B1
Molecular weight:
80431
Reactions
ATP + (phosphate)(n) = ADP + (phosphate)(n+1).
General function:
Involved in methionine adenosyltransferase activity
Specific function:
Catalyzes the formation of S-adenosylmethionine from methionine and ATP. The overall synthetic reaction is composed of two sequential steps, AdoMet formation and the subsequent tripolyphosphate hydrolysis which occurs prior to release of AdoMet from the enzyme. Is essential for growth
Gene Name:
metK
Uniprot ID:
P0A817
Molecular weight:
41951
Reactions
ATP + L-methionine + H(2)O = phosphate + diphosphate + S-adenosyl-L-methionine.
General function:
Involved in hydrolase activity
Specific function:
Nucleotidase with a broad substrate specificity as it can dephosphorylate various ribo- and deoxyribonucleoside 5'- monophosphates and ribonucleoside 3'-monophosphates with highest affinity to 3'-AMP. Also hydrolyzes polyphosphate (exopolyphosphatase activity) with the preference for short-chain- length substrates (P20-25). Might be involved in the regulation of dNTP and NTP pools, and in the turnover of 3'-mononucleotides produced by numerous intracellular RNases (T1, T2, and F) during the degradation of various RNAs. Also plays a significant physiological role in stress-response and is required for the survival of E.coli in stationary growth phase
Gene Name:
surE
Uniprot ID:
P0A840
Molecular weight:
26900
Reactions
A 5'-ribonucleotide + H(2)O = a ribonucleoside + phosphate.
A 3'-ribonucleotide + H(2)O = a ribonucleoside + phosphate.
(Polyphosphate)(n) + H(2)O = (polyphosphate)(n-1) + phosphate.
General function:
Involved in ATP binding
Specific function:
Required for both de novo synthesis of the corrin ring for the assimilation of exogenous corrinoids. Participates in the adenosylation of a variety of incomplete and complete corrinoids
Gene Name:
btuR
Uniprot ID:
P0A9H5
Molecular weight:
21999
Reactions
ATP + cob(I)yrinic acid a,c-diamide = triphosphate + adenosylcob(III)yrinic acid a,c-diamide.
ATP + cobinamide = triphosphate + adenosylcobinamide.
General function:
Involved in magnesium ion binding
Specific function:
Degradation of inorganic polyphosphates. Orthophosphate is released progressively from the ends of polyphosphate of circa 500 residues long, while chains of circa 15 residues compete poorly with polyphosphate as substrate
Gene Name:
ppx
Uniprot ID:
P0AFL6
Molecular weight:
58136
Reactions
(Polyphosphate)(n) + H(2)O = (polyphosphate)(n-1) + phosphate.
General function:
Involved in magnesium ion binding
Specific function:
dGTPase preferentially hydrolyzes dGTP over the other canonical NTPs
Gene Name:
dgt
Uniprot ID:
P15723
Molecular weight:
59382
Reactions
dGTP + H(2)O = deoxyguanosine + triphosphate.
General function:
Involved in ATP binding
Specific function:
Converts CNB12 to ADOB12
Gene Name:
eutT
Uniprot ID:
P65643
Molecular weight:
30171
Reactions
ATP + cob(I)yrinic acid a,c-diamide = triphosphate + adenosylcob(III)yrinic acid a,c-diamide.
ATP + cobinamide = triphosphate + adenosylcobinamide.
General function:
Coenzyme transport and metabolism
Specific function:
Catalyzes the conversion of 7,8-dihydroneopterin triphosphate (H2NTP) to 6-carboxy-5,6,7,8-tetrahydropterin (CPH4) and acetaldehyde. Can also convert 6-pyruvoyltetrahydropterin (PPH4) and sepiapterin to CPH4; these 2 compounds are probably intermediates in the reaction from H2NTP
Gene Name:
queD
Uniprot ID:
P65870
Molecular weight:
13773
Reactions
7,8-dihydroneopterin 3'-triphosphate + H(2)O = 6-carboxy-5,6,7,8-tetrahydropterin + acetaldehyde + triphosphate.