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Escherichia coli K-12 substr. MG1655 Compound: diphosphate

Synonyms: PPi, PP, pyrophosphate

Superclasses: an ionan anionan inorganic anionan inorganic phosphorus-containing ionan inorganic phosphatea polyphosphate
an ionan inorganic ionan inorganic anionan inorganic phosphorus-containing ionan inorganic phosphatea polyphosphate

Chemical Formula: HO7P2

Molecular Weight: 174.95 Daltons

Monoisotopic Molecular Weight: 177.9432255031 Daltons

diphosphate compound structure

SMILES: O=P(O)(OP([O-])([O-])=O)[O-]

InChI: InChI=1S/H4O7P2/c1-8(2,3)7-9(4,5)6/h(H2,1,2,3)(H2,4,5,6)/p-3


Unification Links: CAS:2466-09-3, ChEBI:29888, ChemSpider:996, DrugBank:DB04160, HMDB:HMDB00250, IAF1260:33511, KEGG:C00013, MetaboLights:MTBLC33019, PubChem:1023

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -480.93

Reactions known to consume the compound:

Not in pathways:
diphosphate + H2O → 2 phosphate + H+

Reactions known to produce the compound:

1,4-dihydroxy-2-naphthoate biosynthesis :
ATP + 2-succinylbenzoate + coenzyme A → AMP + 4-(2'-carboxyphenyl)-4-oxobutyryl-CoA + diphosphate

2-methylcitrate cycle I :
propanoate + ATP + coenzyme A → propanoyl-CoA + AMP + diphosphate

5-aminoimidazole ribonucleotide biosynthesis I , 5-aminoimidazole ribonucleotide biosynthesis II , superpathway of 5-aminoimidazole ribonucleotide biosynthesis :
5-phospho-β-D-ribosylamine + L-glutamate + diphosphate ← 5-phospho-α-D-ribose 1-diphosphate + L-glutamine + H2O

6-hydroxymethyl-dihydropterin diphosphate biosynthesis I :
7,8-dihydroneopterin 3'-triphosphate + H2O → 7,8-dihydroneopterin 3'-phosphate + diphosphate + H+

acetate conversion to acetyl-CoA :
acetate + ATP + coenzyme A → acetyl-CoA + AMP + diphosphate

adenine and adenosine salvage II :
AMP + diphosphate ← 5-phospho-α-D-ribose 1-diphosphate + adenine

adenine and adenosine salvage III :
IMP + diphosphate ← 5-phospho-α-D-ribose 1-diphosphate + hypoxanthine

adenosylcobalamin salvage from cobinamide I :
adenosyl-cobinamide phosphate + GTP + H+ → adenosylcobinamide-GDP + diphosphate

ADP-L-glycero-β-D-manno-heptose biosynthesis :
D-glycero-β-D-manno-heptose 1-phosphate + ATP + H+ → ADP-D-glycero-β-D-manno-heptose + diphosphate

anhydromuropeptides recycling , UDP-N-acetyl-D-glucosamine biosynthesis I :
N-acetyl-α-D-glucosamine 1-phosphate + UTP + H+ → UDP-N-acetyl-α-D-glucosamine + diphosphate

biotin-carboxyl carrier protein assembly :
a [biotin-carboxyl-carrier protein monomer] + biotin + ATP → AMP + a biotinylated [BCCP monomer] + diphosphate + H+

CDP-diacylglycerol biosynthesis I , CDP-diacylglycerol biosynthesis II :
CTP + a 1,2-diacyl-sn-glycerol 3-phosphate + H+ → a CDP-diacylglycerol + diphosphate

citrate lyase activation :
[a holo citrate lyase acyl-carrier protein] + acetate + ATP → an acetyl-[holo citrate lyase acyl-carrier protein] + AMP + diphosphate
2'-(5''-triphospho-α-D-ribosyl)-3'-dephospho-CoA + [a citrate-lyase acyl-carrier protein] → [a holo citrate lyase acyl-carrier protein] + diphosphate + H+

CMP-3-deoxy-D-manno-octulosonate biosynthesis :
3-deoxy-α-D-manno-octulosonate + CTP → CMP-3-deoxy-β-D-manno-octulosonate + diphosphate

coenzyme A biosynthesis I :
4'-phosphopantetheine + ATP + H+ → 3'-dephospho-CoA + diphosphate
(R)-4'-phosphopantothenate + L-cysteine + CTP → CMP + R-4'-phosphopantothenoyl-L-cysteine + diphosphate + H+

cytidylyl molybdenum cofactor biosynthesis :
CTP + MoO2-molybdopterin cofactor + H+ → cytidylyl molybdenum cofactor + diphosphate

demethylmenaquinol-8 biosynthesis I :
all-trans-octaprenyl diphosphate + 1,4-dihydroxy-2-naphthoate + H+ → CO2 + demethylmenaquinol-8 + diphosphate

di-trans,poly-cis-undecaprenyl phosphate biosynthesis :
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate → di-trans,octa-cis-undecaprenyl diphosphate + 8 diphosphate

enterobactin biosynthesis :
ATP + 2,3-dihydroxybenzoate + H+ → 2,3-dihydroxybenzoyl adenylate + diphosphate

fatty acid β-oxidation I :
a 2,3,4-saturated fatty acid + ATP + coenzyme A → a 2,3,4-saturated fatty acyl CoA + AMP + diphosphate

flavin biosynthesis I (bacteria and plants) :
GTP + 3 H2O → 2,5-diamino-6-(5-phospho-D-ribosylamino)pyrimidin-4(3H)-one + formate + diphosphate + 2 H+
ATP + FMN + H+ → FAD + diphosphate

galactose degradation I (Leloir pathway) , UDP-glucose biosynthesis :
α-D-glucopyranose 1-phosphate + UTP + H+ → UDP-α-D-glucose + diphosphate

Reactions known to both consume and produce the compound:

dTDP-L-rhamnose biosynthesis I , dTDP-N-acetylthomosamine biosynthesis :
α-D-glucopyranose 1-phosphate + dTTP + H+ ↔ dTDP-α-D-glucose + diphosphate

enterobactin biosynthesis :
L-serine + ATP + H+ ↔ L-seryl-adenylate + diphosphate

L-histidine biosynthesis :
1-(5-phospho-β-D-ribosyl)-ATP + diphosphate ↔ ATP + 5-phospho-α-D-ribose 1-diphosphate + H+

N6-L-threonylcarbamoyladenosine37-modified tRNA biosynthesis :
L-threonine + hydrogen carbonate + ATP ↔ L-threonylcarbamoyladenylate + diphosphate + H2O

UMP biosynthesis :
orotidine 5'-phosphate + diphosphate ↔ 5-phospho-α-D-ribose 1-diphosphate + orotate

Not in pathways:
GTP ↔ cyclic-GMP + diphosphate
heme b + (2E,6E)-farnesyl diphosphate + H2O ↔ heme o + diphosphate

In Reactions of unknown directionality:

Not in pathways:
ThiS protein + ATP = ThiS-COAMP + diphosphate
a deoxyribonucleoside triphosphate + (deoxynucleotides)(n) = (deoxynucleotides)(n+1) + diphosphate
ATP + an mRNA = an mRNA + diphosphate
ATP + ATP + H+ = 5',5'''-diadenosine tetraphosphate + diphosphate
a nucleoside triphosphate + RNA(n) = RNA(n+1) + diphosphate
protein chain elongation factor EF-P + (R)-β-lysine + ATP = protein chain elongation factor EF-P, β-lysyl-Lys34 + AMP + diphosphate
dimethylallyl diphosphate + an adenosine37 in tRNA = N6-dimethylallyladenosine37 in tRNA + diphosphate
carbamoyl phosphate + ATP + H2O = O-carbamoyladenylate + diphosphate + phosphate
2 GTP + bis(molybdenum cofactor) + 2 H+ = bis(guanylyl molybdopterin cofactor) + 2 diphosphate
a [lipoyl-carrier protein]-L-lysine + ATP + (R)-lipoate = a [lipoyl-carrier protein]-N6-lipoyl-L-lysine + AMP + diphosphate + H+

In Transport reactions:
an ion[periplasm]an ion[extracellular space]

Enzymes activated by diphosphate, sorted by the type of activation, are:

Activator (Mechanism unknown) of: glutaminase B [Prusiner76], polyphosphate kinase [Comment 1]

Enzymes inhibited by diphosphate, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: xanthosine-5'-phosphate:L-glutamine amido-ligase (AMP-forming) [Spector75, Patel77], pyruvate oxidase [Comment 2], xanthosine-5'-phosphate:ammonia ligase (AMP-forming) [Spector75], GTP cyclohydrolase [Foor75, Ritz01b], pyrophosphohydrolase [OHandley96, Comment 3], polyphosphate kinase [Comment 4], adenine phosphoribosyltransferase [HochstadtOzer71, Comment 5], methylglyoxal synthase [Hopper71, Hopper72, Comment 6] Inhibitor (Noncompetitive) of: arginyl-tRNA synthetase [Charlier79], methionine adenosyltransferase [Markham80], quinolinate phosphoribosyltransferase (decarboxylating) [Bhatia96], adenylate cyclase [Yang83a] Inhibitor (Mechanism unknown) of: acetyl-CoA synthetase (AMP-forming) [Barak04], thiamine phosphate synthase [Kayama73, Kawasaki79], glucose-1-phosphate adenylyltransferase [Preiss83], galactarate dehydratase [Blumenthal66, Blumenthal64], dTDP-glucose pyrophosphorylase [Zuccotti01, Comment 7], α-dehydro-β-deoxy-D-glucarate aldolase [Fish66], nucleoside diphosphate kinase [Roisin78], dihydroneopterin triphosphate pyrophosphohydrolase [Suzuki74, Comment 8], tRNA(i6A37) synthase [Rosenbaum72], glutamine synthetase deadenylase [Shapiro69], thiamine monophosphate kinase [Nishino72], glutamine synthetase adenylyltransferase [Ebner70a, Helmward89, Comment 9] Inhibitor (Other types) of: aspartate ammonia-lyase

This compound has been characterized as an alternative substrate of the following enzymes: alkaline phosphatase

In Growth Media: PMA phosphorus source test + diphosphate


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OHandley96: O'Handley SF, Frick DN, Bullions LC, Mildvan AS, Bessman MJ (1996). "Escherichia coli orf17 codes for a nucleoside triphosphate pyrophosphohydrolase member of the MutT family of proteins. Cloning, purification, and characterization of the enzyme." J Biol Chem 1996;271(40);24649-54. PMID: 8798731

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Suzuki74: Suzuki Y, Brown GM (1974). "The biosynthesis of folic acid. XII. Purification and properties of dihydroneopterin triphosphate pyrophosphohydrolase." J Biol Chem 1974;249(8);2405-10. PMID: 4362677

Tzeng00: Tzeng CM, Kornberg A (2000). "The multiple activities of polyphosphate kinase of Escherichia coli and their subunit structure determined by radiation target analysis." J Biol Chem 2000;275(6);3977-83. PMID: 10660553

Yang83a: Yang JK, Epstein W (1983). "Purification and characterization of adenylate cyclase from Escherichia coli K12." J Biol Chem 1983;258(6);3750-8. PMID: 6300054

Zuccotti01: Zuccotti S, Zanardi D, Rosano C, Sturla L, Tonetti M, Bolognesi M (2001). "Kinetic and crystallographic analyses support a sequential-ordered bi bi catalytic mechanism for Escherichia coli glucose-1-phosphate thymidylyltransferase." J Mol Biol 313(4);831-43. PMID: 11697907

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Please cite the following article in publications resulting from the use of EcoCyc: Nucleic Acids Research 41:D605-12 2013
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