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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:14:39 UTC

HMDB ID

HMDB0000250

Secondary Accession Numbers

HMDB00250

Metabolite Identification

Common Name

Pyrophosphate

Description

The 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.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View Stereo Labels

Synonyms

Value	Source
[(HO)2P(O)OP(O)(OH)2]	ChEBI
Acide diphosphorique	ChEBI
Diphosphorsaeure	ChEBI
H4P2O7	ChEBI
Pyrophosphoric acid	ChEBI
Pyrophosphorsaeure	ChEBI
Diphosphoric acid	Kegg
PPi	Kegg
Diphosphate	Generator
PYROphosphATE	ChEBI
Na4p2O7	MeSH, HMDB
PPi CPD	MeSH, HMDB

Chemical Formula

H₄O₇P₂

Average Molecular Weight

177.9751

Monoisotopic Molecular Weight

177.943225506

IUPAC Name

(phosphonooxy)phosphonic acid

Traditional Name

pyrophosphoric acid

CAS Registry Number

14000-31-8

SMILES

OP(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)

InChI Key

XPPKVPWEQAFLFU-UHFFFAOYSA-N

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.

Kingdom

Inorganic compounds

Super Class

Homogeneous non-metal compounds

Class

Non-metal oxoanionic compounds

Sub Class

Non-metal pyrophosphates

Direct Parent

Non-metal pyrophosphates

Alternative Parents

Inorganic oxides

Substituents

Non-metal pyrophosphate
Inorganic oxide

Molecular Framework

Not Available

External Descriptors

phosphorus oxoacid (CHEBI:29888 )
acyclic phosphorus acid anhydride (CHEBI:29888 )

Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-1.4	ChemAxon
pKa (Strongest Acidic)	1.7	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	124.29 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	25.52 m³·mol⁻¹	ChemAxon
Polarizability	10.28 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	137.213	31661259
DarkChem	[M-H]-	129.173	31661259
AllCCS	[M+H]+	140.441	32859911
AllCCS	[M-H]-	126.722	32859911
DeepCCS	[M+H]+	92.046	30932474
DeepCCS	[M-H]-	88.555	30932474
DeepCCS	[M-2H]-	125.859	30932474
DeepCCS	[M+Na]+	100.582	30932474
AllCCS	[M+H]+	140.4	32859911
AllCCS	[M+H-H2O]+	136.6	32859911
AllCCS	[M+NH4]+	144.0	32859911
AllCCS	[M+Na]+	145.0	32859911
AllCCS	[M-H]-	126.7	32859911
AllCCS	[M+Na-2H]-	129.6	32859911
AllCCS	[M+HCOO]-	132.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Pyrophosphate	OP(O)(=O)OP(O)(O)=O	2996.9	Standard polar	33892256
Pyrophosphate	OP(O)(=O)OP(O)(O)=O	1539.9	Standard non polar	33892256
Pyrophosphate	OP(O)(=O)OP(O)(O)=O	1576.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Pyrophosphate,1TMS,isomer #1	C[Si](C)(C)OP(=O)(O)OP(=O)(O)O	1707.5	Semi standard non polar	33892256
Pyrophosphate,1TMS,isomer #1	C[Si](C)(C)OP(=O)(O)OP(=O)(O)O	1619.8	Standard non polar	33892256
Pyrophosphate,1TMS,isomer #1	C[Si](C)(C)OP(=O)(O)OP(=O)(O)O	2406.6	Standard polar	33892256
Pyrophosphate,2TMS,isomer #1	C[Si](C)(C)OP(=O)(O[Si](C)(C)C)OP(=O)(O)O	1727.8	Semi standard non polar	33892256
Pyrophosphate,2TMS,isomer #1	C[Si](C)(C)OP(=O)(O[Si](C)(C)C)OP(=O)(O)O	1745.4	Standard non polar	33892256
Pyrophosphate,2TMS,isomer #1	C[Si](C)(C)OP(=O)(O[Si](C)(C)C)OP(=O)(O)O	2085.9	Standard polar	33892256
Pyrophosphate,2TMS,isomer #2	C[Si](C)(C)OP(=O)(O)OP(=O)(O)O[Si](C)(C)C	1707.6	Semi standard non polar	33892256
Pyrophosphate,2TMS,isomer #2	C[Si](C)(C)OP(=O)(O)OP(=O)(O)O[Si](C)(C)C	1695.4	Standard non polar	33892256
Pyrophosphate,2TMS,isomer #2	C[Si](C)(C)OP(=O)(O)OP(=O)(O)O[Si](C)(C)C	2101.0	Standard polar	33892256
Pyrophosphate,3TMS,isomer #1	C[Si](C)(C)OP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1712.4	Semi standard non polar	33892256
Pyrophosphate,3TMS,isomer #1	C[Si](C)(C)OP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1768.3	Standard non polar	33892256
Pyrophosphate,3TMS,isomer #1	C[Si](C)(C)OP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1946.9	Standard polar	33892256
Pyrophosphate,4TMS,isomer #1	C[Si](C)(C)OP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1771.1	Semi standard non polar	33892256
Pyrophosphate,4TMS,isomer #1	C[Si](C)(C)OP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1798.7	Standard non polar	33892256
Pyrophosphate,4TMS,isomer #1	C[Si](C)(C)OP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1814.7	Standard polar	33892256
Pyrophosphate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O)OP(=O)(O)O	1971.0	Semi standard non polar	33892256
Pyrophosphate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O)OP(=O)(O)O	1837.6	Standard non polar	33892256
Pyrophosphate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O)OP(=O)(O)O	2549.1	Standard polar	33892256
Pyrophosphate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O	2163.0	Semi standard non polar	33892256
Pyrophosphate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O	2117.0	Standard non polar	33892256
Pyrophosphate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O	2375.6	Standard polar	33892256
Pyrophosphate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C	2149.1	Semi standard non polar	33892256
Pyrophosphate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C	2140.2	Standard non polar	33892256
Pyrophosphate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C	2412.2	Standard polar	33892256
Pyrophosphate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2308.3	Semi standard non polar	33892256
Pyrophosphate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2302.0	Standard non polar	33892256
Pyrophosphate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2297.6	Standard polar	33892256
Pyrophosphate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2492.5	Semi standard non polar	33892256
Pyrophosphate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2419.1	Standard non polar	33892256
Pyrophosphate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2236.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Pyrophosphate GC-EI-TOF (Non-derivatized)	splash10-0002-0972000000-a80f120dd426991d6eff	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Pyrophosphate GC-EI-TOF (Non-derivatized)	splash10-0udi-0741900000-9c5b3c334561dd282116	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Pyrophosphate GC-EI-TOF (Non-derivatized)	splash10-03di-0920000000-a5ad76aa129d898d71f8	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Pyrophosphate GC-EI-TOF (Non-derivatized)	splash10-03di-0910000000-531d3e19493dc29d6e5c	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Pyrophosphate GC-MS (4 TMS)	splash10-0udi-0320900000-0abbcb28a43d7e24fe81	2018-05-17	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Pyrophosphate GC-MS (Non-derivatized)	splash10-0udi-0320900000-0abbcb28a43d7e24fe81	2018-05-17	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pyrophosphate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9200000000-47d5c2340766aaf36e95	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pyrophosphate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pyrophosphate Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-004j-5900000000-6633d5123eb37c266247	2018-05-17	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pyrophosphate Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0002-9000000000-1274b83242b279e9dac7	2018-05-17	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pyrophosphate Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-001i-9000000000-69bc4c795fec87fef4b8	2018-05-17	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pyrophosphate QqQ 1V, negative-QTOF	splash10-0udi-0009000000-0d7e21d878a866bb58ce	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pyrophosphate QqQ 2V, negative-QTOF	splash10-0a4i-0009000000-886725ef1e6e856bba4e	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pyrophosphate QqQ 3V, negative-QTOF	splash10-0udi-0009000000-6ea52df356fc0219aae7	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pyrophosphate QqQ 4V, negative-QTOF	splash10-0udi-0009000000-bb05c17fd2d302e48d47	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pyrophosphate QqQ 5V, negative-QTOF	splash10-0udi-0109000000-884206603f4eb302c100	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pyrophosphate QqQ 6V, negative-QTOF	splash10-0udi-0109000000-f6479c3c70cf1da434a7	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pyrophosphate QqQ 7V, negative-QTOF	splash10-0udi-0219000000-8c9d253d3347c2b2a7b1	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pyrophosphate QqQ 8V, negative-QTOF	splash10-0ufr-0529000000-40db63b6f9bc6df64259	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pyrophosphate QqQ 9V, negative-QTOF	splash10-0a6r-0938000000-128abea42399dbbd6b73	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pyrophosphate QqQ 10V, negative-QTOF	splash10-004i-0923000000-bf96528807a30d13e941	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pyrophosphate QqQ 11V, negative-QTOF	splash10-004i-0922000000-7ba3aaba52e7bda31d59	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pyrophosphate QqQ 12V, negative-QTOF	splash10-004i-0911000000-729a221aabae27701a80	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pyrophosphate QqQ 13V, negative-QTOF	splash10-004i-0910000000-2fc64e199062885202b2	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pyrophosphate QqQ 14V, negative-QTOF	splash10-004i-0910000000-0d1641e2522b985110a8	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pyrophosphate QqQ 15V, negative-QTOF	splash10-004i-0910000000-fca1eea6589ac6828b32	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pyrophosphate QqQ 16V, negative-QTOF	splash10-004i-0900000000-6fae5d4a6887e1ace201	2020-07-22	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyrophosphate 10V, Positive-QTOF	splash10-004j-4900000000-fab623ebd43ab1452b9f	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyrophosphate 20V, Positive-QTOF	splash10-0002-9400000000-b2565f0d436385569cff	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyrophosphate 40V, Positive-QTOF	splash10-000t-9300000000-ac978f84efc222da7b43	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyrophosphate 10V, Negative-QTOF	splash10-004i-0900000000-21c64963e1ff18b360e1	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyrophosphate 20V, Negative-QTOF	splash10-004i-9700000000-54e41043f009fe6db86c	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyrophosphate 40V, Negative-QTOF	splash10-004i-9000000000-2a5f69c16aa671275a62	2015-09-15	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Mitochondria
Nucleus
Endoplasmic reticulum
Peroxisome

Biospecimen Locations

Blood
Saliva
Urine

Tissue Locations

Epidermis
Fibroblasts
Intestine
Neuron
Platelet
Prostate
Skeletal Muscle
Testis

Pathways

Name	SMPDB/PathBank	KEGG
Transcription/Translation	SMP00019	Not Available
Alanine, aspartate and glutamate metabolism	Not Available
Primary Hyperoxaluria Type I		Not Available
Pyruvate Carboxylase Deficiency		Not Available
Lactic Acidemia		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	1.8 (0.64-2.96) uM	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Urine	Detected and Quantified	2.56 +/- 1.22 umol/mmol creatinine	Children (1-13 years old)	Both	Normal	Geigy Scientific ...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	28157703	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB04160

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00019561

Chemspider ID

Not Available

KEGG Compound ID

C00013

BioCyc ID

PPI

BiGG ID

Not Available

Wikipedia Link

Pyrophosphate

METLIN ID

Not Available

PubChem Compound

1023

PDB ID

Not Available

ChEBI ID

29888

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

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)

Not Available

General References

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 ]
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. [PubMed:19212411 ]
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 ]
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. 1980 Dec;88(6):1785-92. [PubMed:6780546 ]
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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 ]

Only showing the first 10 proteins. There are 351 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Acetyl-coenzyme A synthetase, cytoplasmic

General function:: Involved in acetate-CoA ligase activity
Specific function:: Activates acetate so that it can be used for lipid synthesis or for energy generation.
Gene Name:: ACSS2
Uniprot ID:: Q9NR19
Molecular weight:: 78579.11

Reactions

Adenosine triphosphate + Acetic acid + Coenzyme A → Adenosine monophosphate + Pyrophosphate + Acetyl-CoA	details
Adenosine triphosphate + Acetic acid → Pyrophosphate + Acetyl adenylate	details
Adenosine triphosphate + Propionic acid → Pyrophosphate + Propinol adenylate	details

Enzyme Details

2. Acetyl-coenzyme A synthetase 2-like, mitochondrial

General function:: Involved in acetate-CoA ligase activity
Specific function:: Important for maintaining normal body temperature during fasting and for energy homeostasis. Essential for energy expenditure under ketogenic conditions (By similarity). Converts acetate to acetyl-CoA so that it can be used for oxidation through the tricarboxylic cycle to produce ATP and CO(2).
Gene Name:: ACSS1
Uniprot ID:: Q9NUB1
Molecular weight:: 74625.88

Reactions

Adenosine triphosphate + Acetic acid + Coenzyme A → Adenosine monophosphate + Pyrophosphate + Acetyl-CoA	details
Adenosine triphosphate + Acetic acid → Pyrophosphate + Acetyl adenylate	details
Adenosine triphosphate + Propionic acid → Pyrophosphate + Propinol adenylate	details

Enzyme Details

3. Serum paraoxonase/lactonase 3

General function:: Involved in arylesterase activity
Specific function:: Has low activity towards the organophosphate paraxon and aromatic carboxylic acid esters. Rapidly hydrolyzes lactones such as statin prodrugs (e.g. lovastatin). Hydrolyzes aromatic lactones and 5- or 6-member ring lactones with aliphatic substituents but not simple lactones or those with polar substituents.
Gene Name:: PON3
Uniprot ID:: Q15166
Molecular weight:: 39607.185

Enzyme Details

4. Fucose-1-phosphate guanylyltransferase

General function:: Involved in fucose-1-phosphate guanylyltransferase acti
Specific function:: Catalyzes the formation of GDP-L-fucose from GTP and L-fucose-1-phosphate. Functions as a salvage pathway to reutilize L-fucose arising from the turnover of glycoproteins and glycolipids.
Gene Name:: FPGT
Uniprot ID:: O14772
Molecular weight:: 37630.405

Reactions

Guanosine triphosphate + Fucose 1-phosphate → Pyrophosphate + GDP-L-fucose	details

Enzyme Details

5. Squalene synthase

General function:: Involved in transferase activity
Specific function:: Not Available
Gene Name:: FDFT1
Uniprot ID:: P37268
Molecular weight:: 48114.87

Reactions

Farnesyl pyrophosphate + NAD(P)H → Squalene + Pyrophosphate + NAD(P)(+)	details
Farnesyl pyrophosphate → Pyrophosphate + Presqualene diphosphate	details
Presqualene diphosphate + NADPH + Hydrogen Ion → Pyrophosphate + Squalene + NADP	details
Farnesyl pyrophosphate + NADPH + Hydrogen Ion → Squalene + Pyrophosphate + NADP	details

Enzyme Details

6. Phenylalanine--tRNA ligase alpha subunit

General function:: Involved in nucleotide binding
Specific function:: Not Available
Gene Name:: FARSA
Uniprot ID:: Q9Y285
Molecular weight:: 57563.225

Reactions

Adenosine triphosphate + Phenylalanine + tRNA(Phe) → Adenosine monophosphate + Pyrophosphate + L-phenylalanyl-tRNA(Phe)	details
Adenosine triphosphate + Phenylalanine + tRNA(Phe) → Adenosine monophosphate + Pyrophosphate + L-Phenylalanyl-tRNA(Phe)	details

Enzyme Details

7. Phenylalanine--tRNA ligase, mitochondrial

General function:: Involved in nucleotide binding
Specific function:: Catalyzes direct attachment of p-Tyr (Tyr) to tRNAPhe. Permits also, with a lower efficiency, the attachment of m-Tyr to tRNAPhe, thereby opening the way for delivery of the misacylated tRNA to the ribosome and incorporation of ROS-damaged amino acid into proteins.
Gene Name:: FARS2
Uniprot ID:: O95363
Molecular weight:: 52356.21

Reactions

Adenosine triphosphate + Phenylalanine + tRNA(Phe) → Adenosine monophosphate + Pyrophosphate + L-phenylalanyl-tRNA(Phe)	details
Adenosine triphosphate + Phenylalanine + tRNA(Phe) → Adenosine monophosphate + Pyrophosphate + L-Phenylalanyl-tRNA(Phe)	details

Enzyme Details

8. Alpha-aminoadipic semialdehyde dehydrogenase

General function:: Involved in oxidoreductase activity
Specific function:: Multifunctional enzyme mediating important protective effects. Metabolizes betaine aldehyde to betaine, an important cellular osmolyte and methyl donor. Protects cells from oxidative stress by metabolizing a number of lipid peroxidation-derived aldehydes. Involved in lysine catabolism.
Gene Name:: ALDH7A1
Uniprot ID:: P49419
Molecular weight:: 58486.74

Reactions

Aminoadipic acid + Adenosine triphosphate → L-2-Aminoadipate adenylate + Pyrophosphate	details

Enzyme Details

9. Amidophosphoribosyltransferase

General function:: Involved in amidophosphoribosyltransferase activity
Specific function:: Not Available
Gene Name:: PPAT
Uniprot ID:: Q06203
Molecular weight:: 57398.52

Reactions

5-Phosphoribosylamine + Pyrophosphate + Glutamic acid → Glutamine + Phosphoribosyl pyrophosphate + Water	details

Enzyme Details

10. Nicotinamide mononucleotide adenylyltransferase 1

General function:: Involved in nucleotidyltransferase activity
Specific function:: Catalyzes the formation of NAD(+) from nicotinamide mononucleotide (NMN) and ATP. Can also use the deamidated form; nicotinic acid mononucleotide (NaMN) as substrate with the same efficiency. Can use triazofurin monophosphate (TrMP) as substrate. Also catalyzes the reverse reaction, i.e. the pyrophosphorolytic cleavage of NAD(+). For the pyrophosphorolytic activity, prefers NAD(+) and NAAD as substrates and degrades NADH, nicotinic acid adenine dinucleotide phosphate (NHD) and nicotinamide guanine dinucleotide (NGD) less effectively. Fails to cleave phosphorylated dinucleotides NADP(+), NADPH and NAADP(+). Protects against axonal degeneration following mechanical or toxic insults.
Gene Name:: NMNAT1
Uniprot ID:: Q9HAN9
Molecular weight:: 31932.22

Reactions

Adenosine triphosphate + Nicotinamide ribotide → Pyrophosphate + NAD	details
Adenosine triphosphate + beta-nicotinate-D-ribonucleotide → Pyrophosphate + Nicotinic acid adenine dinucleotide	details
Adenosine triphosphate + Nicotinic acid mononucleotide → Pyrophosphate + Nicotinic acid adenine dinucleotide	details

Only showing the first 10 proteins. There are 351 proteins in total.

Show all enzymes and transporters

Showing metabocard for Pyrophosphate (HMDB0000250)

MOL for HMDB0000250 (Pyrophosphate)

3D MOL for HMDB0000250 (Pyrophosphate)

3D SDF for HMDB0000250 (Pyrophosphate)

3D-SDF for HMDB0000250 (Pyrophosphate)

PDB for HMDB0000250 (Pyrophosphate)

3D PDB for HMDB0000250 (Pyrophosphate)

SMILES for HMDB0000250 (Pyrophosphate)

INCHI for HMDB0000250 (Pyrophosphate)

Structure for HMDB0000250 (Pyrophosphate)

3D Structure for HMDB0000250 (Pyrophosphate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra

Enzymes

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