| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2005-11-16 08:48:42 -0700 |
| Update Date |
2013-02-08 17:08:10 -0700 |
| HMDB ID |
HMDB00250 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
|---|
| Common Name |
Pyrophosphate |
| Description |
In chemistry, the anion, the salts, and the esters of pyrophosphoric acid are called pyrophosphates. The 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. |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- (4-)Diphosphoric acid ion
- (P2O74-)Diphosphate
- Diphosphate
- Diphosphoric acid
- PPi
- Pyrometaphosphate
- Pyrophosphate
- Pyrophosphate tetraanion
- Pyrophosphate(4-) ion
|
| Chemical Formula |
O7P2 |
| Average Molecular Weight |
173.9433 |
| Monoisotopic Molecular Weight |
173.911925378 |
| IUPAC Name |
(phosphonatooxy)phosphonate |
| Traditional IUPAC Name |
phosphonatooxyphosphonate |
| CAS Registry Number |
14000-31-8 |
| SMILES |
[O-]P([O-])(=O)OP([O-])([O-])=O |
| InChI Identifier |
InChI=1S/H4O7P2/c1-8(2,3)7-9(4,5)6/h(H2,1,2,3)(H2,4,5,6)/p-4 |
| InChI Key |
XPPKVPWEQAFLFU-UHFFFAOYSA-J |
| Chemical Taxonomy |
|---|
| Kingdom |
Inorganic Compounds |
| Super Class |
Homogeneous Non-metal Compounds |
| Class |
Non-metal Oxoanionic Compounds |
| Sub Class |
Non-metal Pyrophosphates |
| Other Descriptors |
- phosphorus oxoanion(ChEBI)
|
| Substituents |
|
| Direct Parent |
Non-metal Pyrophosphates |
| Ontology |
|---|
| Status |
Detected and Quantified |
| Origin |
|
| Biofunction |
- Component of Alanine and aspartate metabolism
- Component of Aminoacyl-tRNA biosynthesis
- Component of Aminophosphonate metabolism
- Component of Aminosugars metabolism
- Component of Arginine and proline metabolism
- Component of Biotin metabolism
- Component of Fatty acid metabolism
- Component of Folate biosynthesis
- Component of Fructose and mannose metabolism
- Component of Galactose metabolism
- Component of Glutamate metabolism
- Component of Glycerophospholipid metabolism
- Component of Glycine, serine and threonine metabolism
- Component of Histidine metabolism
- Component of Lysine biosynthesis
- Component of Methionine metabolism
- Component of Nicotinate and nicotinamide metabolism
- Component of Nitrogen metabolism
- Component of Nucleotide sugars metabolism
- Component of Phenylalanine, tyrosine and tryptophan biosynthesis
- Component of Porphyrin and chlorophyll metabolism
- Component of Propanoate metabolism
- Component of Purine metabolism
- Component of Pyrimidine metabolism
- Component of Pyruvate metabolism
- Component of Selenoamino acid metabolism
- Component of Starch and sucrose metabolism
- Component of Sulfur metabolism
- Component of Terpenoid biosynthesis
- Component of Tryptophan metabolism
- Component of Valine, leucine and isoleucine biosynthesis
|
| Application |
Not Available |
| Cellular locations |
- Cytoplasm
- Mitochondria
- Nucleus
- Endoplasmic reticulum
- Peroxisome
|
| Physical Properties |
|---|
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
61 °C |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
Not Available |
Not Available |
| LogP |
Not Available |
Not Available |
|
| Predicted Properties |
|
| Spectra |
|---|
|
|
| Biological Properties |
|---|
| Cellular Locations |
- Cytoplasm
- Mitochondria
- Nucleus
- Endoplasmic reticulum
- Peroxisome
|
| Biofluid Locations |
|
| Tissue Location |
- Skeletal Muscle
- Fibroblasts
- Intestine
- Neuron
- Testes
- Epidermis
- Prostate
- Platelet
|
| Pathways |
| Name |
SMPDB Link |
KEGG Link |
| Transcription/Translation |
SMP00019
|
Not Available
|
|
| Normal Concentrations |
|---|
|
| Blood |
Detected and Quantified |
|
1.8 (0.64-2.96) uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
2.56 +/- 1.22 umol/mmol creatinine |
Children (1-13 year old) |
Both |
Normal |
Not Available |
|
| Abnormal Concentrations |
|---|
|
Not Available |
| Associated Disorders and Diseases |
|---|
| Disease References |
None |
| Associated OMIM IDs |
None |
| External Links |
|---|
| DrugBank ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB021918 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
559142  |
| KEGG Compound ID |
C00013 |
| BioCyc ID |
PPI |
| BiGG ID |
33511 |
| Wikipedia Link |
Pyrophosphate |
| NuGOwiki Link |
HMDB00250 |
| Metagene Link |
HMDB00250 |
| METLIN ID |
3306 |
| PubChem Compound |
644102 |
| PDB ID |
DPO |
| ChEBI ID |
18361 |
| References |
|---|
| Synthesis Reference |
Dittmer, Donald C.; Silverstein, V. Opshelor. Production of pyrophosphate from S-n-butyl phosphorothioate. Journal of Organic Chemistry (1961), 26 4706-7. |
| Material Safety Data Sheet (MSDS) |
Download (PDF)
|
| General References |
- 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.
Pubmed: 6670282
- 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.
Pubmed: 15061376
- 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.
Pubmed: 12189014
- 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.
Pubmed: 7072418
- 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.
Pubmed: 12806625
- 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.
Pubmed: 11718694
- 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.
Pubmed: 3395157
- 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.
Pubmed: 15871634
- 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.
Pubmed: 2984240
- 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.
Pubmed: 15837884
- 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.
Pubmed: 6091528
- 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.
Pubmed: 16291239
- 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.
Pubmed: 8436160
- 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.
Pubmed: 8327563
- 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.
Pubmed: 10749145
- 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.
Pubmed: 9210656
- Hamagishi Y, Oki T, Tone H, Inui T: A radioimmunoassay for guanosine-5'-diphosphate-3'-diphosphate and adenosine-5'-triphosphate-3'-diphosphate. J Biochem (Tokyo). 1980 Dec;88(6):1785-92.
Pubmed: 6780546
- 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.
Pubmed: 15541077
- 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.
Pubmed: 2163407
- 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.
Pubmed: 19212411
|
| Enzymes |
|---|
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| Name: |
Squalene synthase
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| Reactions: |
- (1) (1a) 2 farnesyl diphosphate = diphosphate + presqualene diphosphate [RN:R00702]
- (2) (1b) presqualene diphosphate + NAD(P)H + H+ = squalene + diphosphate + NAD(P)+ [RN:R02872]
|
| Gene Name: |
FDFT1 |
| Uniprot ID: |
P37268 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Biotin--protein ligase
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| Reactions: |
- ATP + biotin + apo-[acetyl-CoA:carbon-dioxide ligase (ADP-forming)] = AMP + diphosphate + [acetyl-CoA:carbon-dioxide ligase (ADP-forming)] [RN:R04562]
|
| Gene Name: |
HLCS |
| Uniprot ID: |
P50747 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Glycyl-tRNA synthetase
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| Reactions: |
- ATP + glycine + tRNAGly = AMP + diphosphate + glycyl-tRNAGly [RN:R03654]
|
| Gene Name: |
GARS |
| Uniprot ID: |
P41250 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Asparagine synthetase [glutamine-hydrolyzing]
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| Reactions: |
- (1) ATP + L-aspartate + L-glutamine + H2O = AMP + diphosphate + L-asparagine + L-glutamate [RN:R00578]
- (2) (1a) L-glutamine + H2O = L-glutamate + NH3 [RN:R00256]
- (3) (1b) ATP + L-aspartate + NH3 = AMP + diphosphate + L-asparagine [RN:R00483]
|
| Gene Name: |
ASNS |
| Uniprot ID: |
P08243 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
DNA ligase 4
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| Reactions: |
- ATP + (deoxyribonucleotide)n + (deoxyribonucleotide)m = AMP + diphosphate + (deoxyribonucleotide)n+m [RN:R00381]
|
| Gene Name: |
LIG4 |
| Uniprot ID: |
P49917 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
DNA ligase 3
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| Reactions: |
- ATP + (deoxyribonucleotide)n + (deoxyribonucleotide)m = AMP + diphosphate + (deoxyribonucleotide)n+m [RN:R00381]
|
| Gene Name: |
LIG3 |
| Uniprot ID: |
P49916 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Lysyl-tRNA synthetase
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| Reactions: |
- ATP + L-lysine + tRNALys = AMP + diphosphate + L-lysyl-tRNALys [RN:R03658]
|
| Gene Name: |
KARS |
| Uniprot ID: |
Q15046 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Valyl-tRNA synthetase
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| Reactions: |
- ATP + L-valine + tRNAVal = AMP + diphosphate + L-valyl-tRNAVal [RN:R03665]
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| Gene Name: |
VARS |
| Uniprot ID: |
P26640 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Argininosuccinate synthase
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| Reactions: |
- ATP + L-citrulline + L-aspartate = AMP + diphosphate + 2-(Nomega-L-arginino)succinate [RN:R01954]
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| Gene Name: |
ASS1 |
| Uniprot ID: |
P00966 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
| Name: |
DNA ligase 1
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| Reactions: |
- ATP + (deoxyribonucleotide)n + (deoxyribonucleotide)m = AMP + diphosphate + (deoxyribonucleotide)n+m [RN:R00381]
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| Gene Name: |
LIG1 |
| Uniprot ID: |
P18858 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Farnesyl pyrophosphate synthase
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| Reactions: |
- geranyl diphosphate + isopentenyl diphosphate = diphosphate + trans,trans-farnesyl diphosphate [RN:R02003]
|
| Gene Name: |
FDPS |
| Uniprot ID: |
P14324 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
| Name: |
DNA polymerase beta
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| Reactions: |
- deoxynucleoside triphosphate + DNAn = diphosphate + DNAn+1 [RN:R00379]
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| Gene Name: |
POLB |
| Uniprot ID: |
P06746 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
DNA polymerase lambda
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| Reactions: |
- deoxynucleoside triphosphate + DNAn = diphosphate + DNAn+1 [RN:R00379]
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| Gene Name: |
POLL |
| Uniprot ID: |
Q9UGP5 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
DNA polymerase eta
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| Reactions: |
- deoxynucleoside triphosphate + DNAn = diphosphate + DNAn+1 [RN:R00379]
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| Gene Name: |
POLH |
| Uniprot ID: |
Q9Y253 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
DNA polymerase mu
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| Reactions: |
- deoxynucleoside triphosphate + DNAn = diphosphate + DNAn+1 [RN:R00379]
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| Gene Name: |
POLM |
| Uniprot ID: |
Q9NP87 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
DNA polymerase kappa
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| Reactions: |
- deoxynucleoside triphosphate + DNAn = diphosphate + DNAn+1 [RN:R00379]
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| Gene Name: |
POLK |
| Uniprot ID: |
Q9UBT6 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
DNA polymerase iota
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| Reactions: |
- deoxynucleoside triphosphate + DNAn = diphosphate + DNAn+1 [RN:R00379]
|
| Gene Name: |
POLI |
| Uniprot ID: |
Q9UNA4 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
mRNA-capping enzyme
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| Reactions: |
- a 5'-phosphopolynucleotide + H2O = a polynucleotide + phosphate [RN:R02249]
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| Gene Name: |
RNGTT |
| Uniprot ID: |
O60942 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Bile acyl-CoA synthetase
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| Reactions: |
- (1) ATP + cholate + CoA = AMP + diphosphate + choloyl-CoA [RN:R02794]
- (2) ATP + (25R)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-oate + CoA = AMP + diphosphate + (25R)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestanoyl-CoA [RN:R04580]
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| Gene Name: |
SLC27A5 |
| Uniprot ID: |
Q9Y2P5 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
FAD synthase
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| Reactions: |
- ATP + FMN = diphosphate + FAD [RN:R00161]
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| Gene Name: |
FLAD1 |
| Uniprot ID: |
Q8NFF5 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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