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Record Information
Version2.0
Creation Date2014-10-02 18:55:54 UTC
Update Date2018-03-21 17:46:20 UTC
Accession NumberT3D4959
Identification
Common NamePyrophosphate
ClassSmall Molecule
DescriptionThe anion, the salts, and the esters of pyrophosphoric acid are called pyrophosphates. The pyrophosphate anion is abbreviated PPi and is formed by the hydrolysis of ATP into AMP in cells. This hydrolysis is called pyrophosphorolysis. The pyrophosphate anion has the structure P2O74-, and is an acid anhydride of phosphate. It is unstable in aqueous solution and rapidly hydrolyzes into inorganic phosphate. Pyrophosphate is an osteotoxin (arrests bone development) and an arthritogen (promotes arthritis). It is also a metabotoxin (an endogenously produced metabolite that causes adverse health affects at chronically high levels). Chronically high levels of pyrophosphate are associated with hypophosphatasia. Hypophosphatasia (also called deficiency of alkaline phosphatase or phosphoethanolaminuria) is a rare, and sometimes fatal, metabolic bone disease. Hypophosphatasia is associated with a molecular defect in the gene encoding tissue non-specific alkaline phosphatase (TNSALP). TNSALP is an enzyme that is tethered to the outer surface of osteoblasts and chondrocytes. TNSALP hydrolyzes several substances, including inorganic pyrophosphate (PPi) and pyridoxal 5'-phosphate (PLP), a major form of vitamin B6. When TSNALP is low, inorganic pyrophosphate (PPi) accumulates outside of cells and inhibits the formation of hydroxyapatite, one of the main components of bone, causing rickets in infants and children and osteomalacia (soft bones) in adults. Vitamin B6 must be dephosphorylated by TNSALP before it can cross the cell membrane. Vitamin B6 deficiency in the brain impairs synthesis of neurotransmitters which can cause seizures. In some cases, a build-up of calcium pyrophosphate dihydrate crystals in the joints can cause pseudogout.
Compound Type
  • Animal Toxin
  • Metabolite
  • Natural Compound
Chemical Structure
Thumb
Synonyms
Synonym
(4-)Diphosphoric acid ion
(P2O74-)Diphosphate
Diphosphate
Diphosphoric acid
PPi
Pyrometaphosphate
Pyrophosphate tetraanion
Pyrophosphate(4-) ion
Pyrophosphic acid
Chemical FormulaO7P2
Average Molecular Mass173.946 g/mol
Monoisotopic Mass173.914 g/mol
CAS Registry Number14000-31-8
IUPAC Name(phosphonooxy)phosphonic acid
Traditional Namepyrophosphoric acid
SMILES[O-]P([O-])(=O)OP([O-])([O-])=O
InChI IdentifierInChI=1S/H4O7P2/c1-8(2,3)7-9(4,5)6/h(H2,1,2,3)(H2,4,5,6)/p-4
InChI KeyInChIKey=XPPKVPWEQAFLFU-UHFFFAOYSA-J
Chemical Taxonomy
Description belongs to the class of inorganic compounds known as non-metal pyrophosphates. These are inorganic non-metallic compounds containing a pyrophosphate as its largest oxoanion.
KingdomInorganic compounds
Super ClassHomogeneous non-metal compounds
ClassNon-metal oxoanionic compounds
Sub ClassNon-metal pyrophosphates
Direct ParentNon-metal pyrophosphates
Alternative Parents
Substituents
  • Non-metal pyrophosphate
  • Inorganic oxide
Molecular FrameworkNot Available
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Cytoplasm
  • Endoplasmic reticulum
  • Mitochondria
  • Nucleus
  • Peroxisome
Biofluid LocationsNot Available
Tissue Locations
  • Epidermis
  • Fibroblasts
  • Intestine
  • Neuron
  • Platelet
  • Prostate
  • Skeletal Muscle
  • Testes
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point61 °C
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
logP-1.4ChemAxon
pKa (Strongest Acidic)1.7ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area124.29 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity25.52 m³·mol⁻¹ChemAxon
Polarizability10.28 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0972000000-a80f120dd426991d6effJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0741900000-9c5b3c334561dd282116JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-03di-0920000000-a5ad76aa129d898d71f8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-03di-0910000000-531d3e19493dc29d6e5cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0udi-0320900000-0abbcb28a43d7e24fe81JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0udi-0320900000-0abbcb28a43d7e24fe81JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9200000000-47d5c2340766aaf36e95JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004j-5900000000-6633d5123eb37c266247JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0002-9000000000-1274b83242b279e9dac7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9000000000-69bc4c795fec87fef4b8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 1V, negativesplash10-0udi-0009000000-0d7e21d878a866bb58ceJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 2V, negativesplash10-0a4i-0009000000-886725ef1e6e856bba4eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 3V, negativesplash10-0udi-0009000000-6ea52df356fc0219aae7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 4V, negativesplash10-0udi-0009000000-bb05c17fd2d302e48d47JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 5V, negativesplash10-0udi-0109000000-884206603f4eb302c100JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 6V, negativesplash10-0udi-0109000000-f6479c3c70cf1da434a7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 7V, negativesplash10-0udi-0219000000-8c9d253d3347c2b2a7b1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 8V, negativesplash10-0ufr-0529000000-40db63b6f9bc6df64259JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 9V, negativesplash10-0a6r-0938000000-128abea42399dbbd6b73JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 10V, negativesplash10-004i-0923000000-bf96528807a30d13e941JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 11V, negativesplash10-004i-0922000000-7ba3aaba52e7bda31d59JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 12V, negativesplash10-004i-0911000000-729a221aabae27701a80JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 13V, negativesplash10-004i-0910000000-2fc64e199062885202b2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 14V, negativesplash10-004i-0910000000-0d1641e2522b985110a8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 15V, negativesplash10-004i-0910000000-fca1eea6589ac6828b32JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 16V, negativesplash10-004i-0900000000-6fae5d4a6887e1ace201JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-4900000000-fab623ebd43ab1452b9fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9400000000-b2565f0d436385569cffJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000t-9300000000-ac978f84efc222da7b43JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-21c64963e1ff18b360e1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9700000000-54e41043f009fe6db86cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-2a5f69c16aa671275a62JSpectraViewer
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsChronically high levels of pyrophosphate are associated with Hypophosphatasia.
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB00250
PubChem Compound ID644102
ChEMBL IDNot Available
ChemSpider ID559142
KEGG IDC00013
UniProt IDNot Available
OMIM ID
ChEBI ID18361
BioCyc IDPPI
CTD IDNot Available
Stitch IDNot Available
PDB IDDPO
ACToR IDNot Available
Wikipedia LinkPyrophosphate
References
Synthesis ReferenceNot Available
MSDST3D4959.pdf
General References
  1. Broll H: [Effect of chloroquine diphosphate on the superhelix structure of DNA and protein synthesis in synovial cells in chronic polyarthritis]. Wien Klin Wochenschr. 1983 Dec 23;95(24):877-80. [6670282 ]
  2. Golanski J, Pluta J, Baraniak J, Watala C: Limited usefulness of the PFA-100 for the monitoring of ADP receptor antagonists--in vitro experience. Clin Chem Lab Med. 2004 Jan;42(1):25-9. [15061376 ]
  3. Mateos-Trigos G, Evans RJ, Heath MF: Effects of P2Y(1) and P2Y(12) receptor antagonists on ADP-induced shape change of equine platelets: comparison with human platelets. Platelets. 2002 Aug-Sep;13(5-6):285-92. [12189014 ]
  4. Sirkis SI: [Serum and cerebrospinal fluid enzyme spectra in meningitis and their differential diagnostic value]. Zh Nevropatol Psikhiatr Im S S Korsakova. 1982;82(2):193-7. [7072418 ]
  5. Barbier O, Torra IP, Sirvent A, Claudel T, Blanquart C, Duran-Sandoval D, Kuipers F, Kosykh V, Fruchart JC, Staels B: FXR induces the UGT2B4 enzyme in hepatocytes: a potential mechanism of negative feedback control of FXR activity. Gastroenterology. 2003 Jun;124(7):1926-40. [12806625 ]
  6. March JG, Simonet BM, Grases F: Determination of pyrophosphate in renal calculi and urine by means of an enzymatic method. Clin Chim Acta. 2001 Dec;314(1-2):187-94. [11718694 ]
  7. Namiki M, Kitamura M, Nonomura N, Sugao H, Nakamura M, Okuyama A, Utsunomiya M, Itatani H, Matsumoto K, Sonoda T: Direct inhibitory effect of estrogen on the human testis in vitro. Arch Androl. 1988;20(2):131-5. [3395157 ]
  8. Kosoglou T, Statkevich P, Johnson-Levonas AO, Paolini JF, Bergman AJ, Alton KB: Ezetimibe: a review of its metabolism, pharmacokinetics and drug interactions. Clin Pharmacokinet. 2005;44(5):467-94. [15871634 ]
  9. Pickett DA, Welch DF: Recognition of Staphylococcus saprophyticus in urine cultures by screening colonies for production of phosphatase. J Clin Microbiol. 1985 Mar;21(3):310-3. [2984240 ]
  10. Hua HT, Albadawi H, Entabi F, Conrad M, Stoner MC, Meriam BT, Sroufe R, Houser S, Lamuraglia GM, Watkins MT: Polyadenosine diphosphate-ribose polymerase inhibition modulates skeletal muscle injury following ischemia reperfusion. Arch Surg. 2005 Apr;140(4):344-51; discussion 351-2. [15837884 ]
  11. Dahlmann N, Ueckermann C: Separation of deoxythymidine-5'-triphosphatase from unspecific hydrolases. A recommended micromethod in the diagnostic evaluation of human carcinoma. Anticancer Res. 1984 Jul-Oct;4(4-5):299-303. [6091528 ]
  12. Ebadi M, Sharma SK, Ghafourifar P, Brown-Borg H, El Refaey H: Peroxynitrite in the pathogenesis of Parkinson's disease and the neuroprotective role of metallothioneins. Methods Enzymol. 2005;396:276-98. [16291239 ]
  13. Tallaksen CM, Sande A, Bohmer T, Bell H, Karlsen J: Kinetics of thiamin and thiamin phosphate esters in human blood, plasma and urine after 50 mg intravenously or orally. Eur J Clin Pharmacol. 1993;44(1):73-8. [8436160 ]
  14. Zhong D, Meins J, Scheidel B, Blume H: [Development of an HPLC method for determination of chloroquine in plasma]. Pharmazie. 1993 May;48(5):349-52. [8327563 ]
  15. Recio JA, Paez JG, Maskeri B, Loveland M, Velasco JA, Notario V: Both normal and transforming PCPH proteins have guanosine diphosphatase activity but only the oncoprotein cooperates with Ras in activating extracellular signal-regulated kinase ERK1. Cancer Res. 2000 Mar 15;60(6):1720-8. [10749145 ]
  16. Puri RN, Colman RF, Colman RW: Modulation of platelet responses by 2-[3-(bromo-2-oxopropylthio)]adenosine-5'-diphosphate involves its binding to as well as covalent modification of an ADP-receptor, aggregin. Arch Biochem Biophys. 1997 Jul 1;343(1):140-5. [9210656 ]
  17. Hamagishi Y, Oki T, Tone H, Inui T: A radioimmunoassay for guanosine-5'-diphosphate-3'-diphosphate and adenosine-5'-triphosphate-3'-diphosphate. J Biochem. 1980 Dec;88(6):1785-92. [6780546 ]
  18. Lee AY, Youm YH, Kim NH, Yang H, Choi WI: Keratinocytes in the depigmented epidermis of vitiligo are more vulnerable to trauma (suction) than keratinocytes in the normally pigmented epidermis, resulting in their apoptosis. Br J Dermatol. 2004 Nov;151(5):995-1003. [15541077 ]
  19. Ito H, Yamamoto H, Kimura Y, Kambe H, Okochi T, Kishimoto S: Affinity chromatography of human plasma gelsolin with polyphosphate compounds on immobilized Cibacron Blue F3GA. J Chromatogr. 1990 Apr 6;526(2):397-406. [2163407 ]
  20. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [19212411 ]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available