You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2006-08-12 19:53:36 UTC
Update Date2013-02-09 00:12:30 UTC
HMDB IDHMDB03379
Secondary Accession NumbersNone
Metabolite Identification
Common NameTriphosphate
DescriptionTriphosphate is a triphosphate is 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 and chlorophyll, the metabolism of Pyrimidine and the metabolism of Thiamine. It is a substrate for Transforming protein p21/H-Ras-1, Bis(5'-adenosyl)-triphosphatase, Ectonucleoside triphosphate diphosphohydrolase 5, Ectonucleoside triphosphate diphosphohydrolase 2, DNA polymerase gamma subunit 1, DNA nucleotidylexotransferase, Inosine triphosphate pyrophosphatase, Cob(I)yrinic acid a,c-diamide adenosyltransferase (mitochondrial), Ectonucleoside triphosphate diphosphohydrolase 1, Ectonucleoside triphosphate diphosphohydrolase 3, Hypothetical protein FLJ13970, Deoxyuridine 5'-triphosphate nucleotidohydrolase (mitochondrial), Thiamine-triphosphatase, DNA-directed RNA polymerase III 32 kDa polypeptide, Ectonucleoside triphosphate diphosphohydrolase 4, 6-pyruvoyl tetrahydrobiopterin synthase and Ectonucleoside triphosphate diphosphohydrolase 6.
Structure
Thumb
Synonyms
  1. Bis(tetraoxidophosphato)dioxidophosphate(5-)
  2. Catena-triphosphate
  3. Inorganic triphosphate
  4. Triphoshoric acid
  5. Triphosphate(5-)
  6. Tripolyphosphate
Chemical FormulaO10P3
Average Molecular Weight252.9153
Monoisotopic Molecular Weight252.870430756
IUPAC Name{[(phosphonatooxy)phosphinato]oxy}phosphonate
Traditional Name(phosphonatooxyphosphinato)oxyphosphonate
CAS Registry Number14127-68-5
SMILES
[O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O
InChI Identifier
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
InChI KeyUNXRWKVEANCORM-UHFFFAOYSA-I
Chemical Taxonomy
KingdomInorganic Compounds
Super ClassHomogeneous Non-metal Compounds
ClassNon-metal Oxoanionic Compounds
Sub ClassNon-metal Pyrophosphates
Other Descriptors
  • a polyphosphate(Cyc)
  • phosphorus oxoanion(ChEBI)
  • triphosphate ion(ChEBI)
Substituents
  • N/A
Direct ParentNon-metal Pyrophosphates
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Folate biosynthesis
  • Component of Porphyrin and chlorophyll metabolism
  • Component of Purine metabolism
  • Component of Pyrimidine metabolism
  • Component of Thiamine metabolism
  • RNA component
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.9ChemAxon
pKa (Strongest Acidic)0.89ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area184.97ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity30.79ChemAxon
Polarizability13.05ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Cerebrospinal Fluid (CSF)
Tissue Location
  • Fibroblasts
  • Kidney
  • Nerve Cells
  • Neuron
  • Pancreas
  • Placenta
  • Platelet
  • Skeletal Muscle
  • Spleen
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified7.88 +/- 0.44 uMAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023159
KNApSAcK IDNot Available
Chemspider ID2683694
KEGG Compound IDC00536
BioCyc IDNot Available
BiGG ID41547
Wikipedia LinkTriphosphoric_acid
NuGOwiki LinkHMDB03379
Metagene LinkHMDB03379
METLIN ID6913
PubChem Compound3440921
PDB IDNot Available
ChEBI ID18036
References
Synthesis ReferenceTsuhako, 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)
General References
  1. Gerasimovskaya EV, Ahmad S, White CW, Jones PL, Carpenter TC, Stenmark KR: Extracellular ATP is an autocrine/paracrine regulator of hypoxia-induced adventitial fibroblast growth. Signaling through extracellular signal-regulated kinase-1/2 and the Egr-1 transcription factor. J Biol Chem. 2002 Nov 22;277(47):44638-50. Epub 2002 Sep 18. Pubmed: 12244041
  2. Cseri J, Szappanos H, Szigeti GP, Csernatony Z, Kovacs L, Csernoch L: A purinergic signal transduction pathway in mammalian skeletal muscle cells in culture. Pflugers Arch. 2002 Mar;443(5-6):731-8. Epub 2001 Dec 4. Pubmed: 11889570
  3. Pelleg A, Schulman ES: Adenosine 5'-triphosphate axis in obstructive airway diseases. Am J Ther. 2002 Sep-Oct;9(5):454-64. Pubmed: 12237739
  4. Ding Z, Kim S, Dorsam RT, Jin J, Kunapuli SP: Inactivation of the human P2Y12 receptor by thiol reagents requires interaction with both extracellular cysteine residues, Cys17 and Cys270. Blood. 2003 May 15;101(10):3908-14. Epub 2003 Jan 30. Pubmed: 12560222
  5. Feng YH, Wang L, Wang Q, Li X, Zeng R, Gorodeski GI: ATP stimulates GRK-3 phosphorylation and beta-arrestin-2-dependent internalization of P2X7 receptor. Am J Physiol Cell Physiol. 2005 Jun;288(6):C1342-56. Epub 2005 Feb 23. Pubmed: 15728711
  6. Smits P, Bijlstra PJ, Russel FG, Lutterman JA, Thien T: Cardiovascular effects of sulphonylurea derivatives. Diabetes Res Clin Pract. 1996 Jul;31 Suppl:S55-9. Pubmed: 8864641
  7. Sawynok J, Liu XJ: Adenosine in the spinal cord and periphery: release and regulation of pain. Prog Neurobiol. 2003 Apr;69(5):313-40. Pubmed: 12787573
  8. Burnstock G: Noradrenaline and ATP: cotransmitters and neuromodulators. J Physiol Pharmacol. 1995 Dec;46(4):365-84. Pubmed: 8770783
  9. Podust VN, Korobeinicheva TO, Nevinskii GA, Rikhter VA, Abramova TI, Lavrik OI: [Template-primer-dependent inactivation of DNA polymerase alpha from human placenta by 2',3'-epoxyadenosine-5'-triphosphate] Bioorg Khim. 1990 Feb;16(2):226-35. Pubmed: 2344386
  10. Valdecantos P, Briones R, Moya P, Germain A, Huidobro-Toro JP: Pharmacological identification of P2X1, P2X4 and P2X7 nucleotide receptors in the smooth muscles of human umbilical cord and chorionic blood vessels. Placenta. 2003 Jan;24(1):17-26. Pubmed: 12495655
  11. Bijlstra PJ, Russel FG, Thien T, Lutterman JA, Smits P: Effects of tolbutamide on vascular ATP-sensitive potassium channels in humans. Comparison with literature data on glibenclamide and glimepiride. Horm Metab Res. 1996 Sep;28(9):512-6. Pubmed: 8911989
  12. Lavoie EG, Kukulski F, Levesque SA, Lecka J, Sevigny J: Cloning and characterization of mouse nucleoside triphosphate diphosphohydrolase-3. Biochem Pharmacol. 2004 May 15;67(10):1917-26. Pubmed: 15130768
  13. Banks FC, Knight GE, Calvert RC, Turmaine M, Thompson CS, Mikhailidis DP, Morgan RJ, Burnstock G: Smooth muscle and purinergic contraction of the human, rabbit, rat, and mouse testicular capsule. Biol Reprod. 2006 Mar;74(3):473-80. Epub 2005 Nov 9. Pubmed: 16280417

Enzymes

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
General function:
Involved in 6-pyruvoyltetrahydropterin synthase activity
Specific function:
Involved in the biosynthesis of tetrahydrobiopterin, an essential cofactor of aromatic amino acid hydroxylases. Catalyzes the transformation of 7,8-dihydroneopterin triphosphate into 6-pyruvoyl tetrahydropterin.
Gene Name:
PTS
Uniprot ID:
Q03393
Molecular weight:
16385.63
Reactions
Dihydroneopterin triphosphate → Dyspropterin + Triphosphatedetails
General function:
Involved in ATP binding
Specific function:
Not Available
Gene Name:
MMAB
Uniprot ID:
Q96EY8
Molecular weight:
27387.975
Reactions
Adenosine triphosphate + Cob(I)yrinate a,c diamide → Triphosphate + adenosylcob(III)yrinic acid a,c-diamidedetails
Adenosine triphosphate + Cobinamide → Triphosphate + Adenosyl cobinamidedetails