ECMDB: Phosphoribosyl pyrophosphate (ECMDB00280) (M2MDB000115)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (12)XML

Proteins (4611)

Record Information

Version

2.0

Creation Date

2012-05-31 10:25:26 -0600

Update Date

2015-06-03 15:53:26 -0600

Secondary Accession Numbers

ECMDB00280

Identification

Name:

Phosphoribosyl pyrophosphate

Description

Phosphoribosyl pyrophosphate (PRPP) is a pentosephosphate. The key substance in the biosynthesis of histidine, tryptophan, and purine and pyrimidine nucleotides. It is formed from ribose 5-phosphate by the enzyme ribose-phosphate diphosphokinase. It plays a role in transferring phosphate groups in several reactions. (Wikipedia)

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms:

α-D-5-P-RibosylPP
α-D-5-phosphoribosylPP
5-phospho-a-D-Ribose 1-diphosphate
5-phospho-a-D-Ribose 1-diphosphoric acid
5-Phospho-a-D-ribose-1-diphosphate
5-phospho-a-D-Ribose-1-diphosphoric acid
5-Phospho-a-D-ribosyl pyrophosphate
5-phospho-a-D-Ribosyl pyrophosphoric acid
5-phospho-a-D-Riobse 1-diphosphate
5-phospho-a-D-Riobse 1-diphosphoric acid
5-phospho-a-delta-Ribose 1-diphosphate
5-phospho-a-delta-Ribose 1-diphosphoric acid
5-phospho-a-delta-Ribose-1-diphosphate
5-phospho-a-delta-Ribose-1-diphosphoric acid
5-phospho-a-delta-Ribosyl pyrophosphate
5-phospho-a-delta-Ribosyl pyrophosphoric acid
5-phospho-a-δ-Ribose 1-diphosphate
5-phospho-a-δ-Ribose 1-diphosphoric acid
5-phospho-a-δ-Ribose-1-diphosphate
5-phospho-a-δ-Ribose-1-diphosphoric acid
5-phospho-a-δ-Ribosyl pyrophosphate
5-phospho-a-δ-Ribosyl pyrophosphoric acid
5-Phospho-alpha-D-ribose 1-diphosphate
5-phospho-alpha-D-Ribose 1-diphosphoric acid
5-Phospho-alpha-D-ribose-1-diphosphate
5-phospho-alpha-D-Ribose-1-diphosphoric acid
5-Phospho-alpha-D-ribosyl pyrophosphate
5-phospho-alpha-D-Ribosyl pyrophosphoric acid
5-Phospho-alpha-D-riobse 1-diphosphate
5-phospho-alpha-D-Riobse 1-diphosphoric acid
5-Phospho-alpha-delta-ribose 1-diphosphate
5-phospho-alpha-delta-Ribose 1-diphosphoric acid
5-Phospho-alpha-delta-ribose-1-diphosphate
5-phospho-alpha-delta-Ribose-1-diphosphoric acid
5-Phospho-alpha-delta-ribosyl pyrophosphate
5-phospho-alpha-delta-Ribosyl pyrophosphoric acid
5-Phospho-ribosyl-pyrophosphate
5-phospho-Ribosyl-pyrophosphoric acid
5-phospho-α-D-Ribose 1-diphosphate
5-phospho-α-D-Ribose 1-diphosphoric acid
5-phospho-α-D-Ribose-1-diphosphate
5-phospho-α-D-Ribose-1-diphosphoric acid
5-phospho-α-D-Ribosyl pyrophosphate
5-phospho-α-D-Ribosyl pyrophosphoric acid
5-phospho-α-D-Riobse 1-diphosphate
5-phospho-α-D-Riobse 1-diphosphoric acid
5-phospho-α-δ-Ribose 1-diphosphate
5-phospho-α-δ-Ribose 1-diphosphoric acid
5-phospho-α-δ-Ribose-1-diphosphate
5-phospho-α-δ-Ribose-1-diphosphoric acid
5-phospho-α-δ-Ribosyl pyrophosphate
5-phospho-α-δ-Ribosyl pyrophosphoric acid
5-Phosphoribose 1-pyrophosphate
5-Phosphoribose 1-pyrophosphoric acid
5-Phosphoribosyl 1-diphosphate
5-Phosphoribosyl 1-diphosphoric acid
5-Phosphoribosyl 1-pyrophosphate
5-Phosphoribosyl 1-pyrophosphoric acid
5-Phosphoribosyl a-1-pyrophosphate
5-Phosphoribosyl a-1-pyrophosphoric acid
5-Phosphoribosyl diphosphate
5-Phosphoribosyl diphosphoric acid
5-Phosphoribosyl-1-PP
5-Phosphoribosyl-1-pyrophosphate
5-Phosphoribosyl-1-pyrophosphoric acid
5-Phosphoribosyl-PP
5-Phosphoribosylpyrophosphate
5-Phosphoribosylpyrophosphoric acid
5-Phosphorylribose 1-a-diphosphate
5-Phosphorylribose 1-a-diphosphoric acid
5-Phosphorylribose 1-alpha-diphosphate
5-Phosphorylribose 1-alpha-diphosphoric acid
5-Phosphorylribose 1-pyrophosphate
5-Phosphorylribose 1-pyrophosphoric acid
5-Phosphorylribose 1-α-diphosphate
5-Phosphorylribose 1-α-diphosphoric acid
5-Phosphorylribosyl 1-pyrophosphate
5-Phosphorylribosyl 1-pyrophosphoric acid
A-D-5-(Dihydrogen phosphate) 1-(trihydrogen pyrophosphate) Ribofuranose
a-D-5-(Dihydrogen phosphoric acid) 1-(trihydrogen pyrophosphoric acid) ribofuranose
a-D-5-P-RibosylPP
A-D-5-Phosphoribosyl 1-pyrophosphate
a-D-5-Phosphoribosyl 1-pyrophosphoric acid
a-D-5-PhosphoribosylPP
A-D-Ribofuranose 5-phosphate 1-pyrophosphate
a-D-Ribofuranose 5-phosphoric acid 1-pyrophosphoric acid
A-D-Ribofuranose, 5-(dihydrogen phosphate) 1-(trihydrogen diphosphate)
a-D-Ribofuranose, 5-(dihydrogen phosphoric acid) 1-(trihydrogen diphosphoric acid)
a-delta-5-(Dihydrogen phosphate) 1-(trihydrogen pyrophosphate) ribofuranose
a-delta-5-(Dihydrogen phosphoric acid) 1-(trihydrogen pyrophosphoric acid) ribofuranose
a-delta-5-Phosphoribosyl 1-pyrophosphate
a-delta-5-Phosphoribosyl 1-pyrophosphoric acid
a-delta-Ribofuranose 5-phosphate 1-pyrophosphate
a-delta-Ribofuranose 5-phosphoric acid 1-pyrophosphoric acid
a-δ-5-(Dihydrogen phosphate) 1-(trihydrogen pyrophosphate) ribofuranose
a-δ-5-(Dihydrogen phosphoric acid) 1-(trihydrogen pyrophosphoric acid) ribofuranose
a-δ-5-Phosphoribosyl 1-pyrophosphate
a-δ-5-Phosphoribosyl 1-pyrophosphoric acid
a-δ-Ribofuranose 5-phosphate 1-pyrophosphate
a-δ-Ribofuranose 5-phosphoric acid 1-pyrophosphoric acid
Alpha-D-5-(Dihydrogen phosphate) 1-(trihydrogen pyrophosphate) Ribofuranose
alpha-D-5-(Dihydrogen phosphoric acid) 1-(trihydrogen pyrophosphoric acid) ribofuranose
Alpha-D-5-P-RibosylPP
Alpha-D-5-Phosphoribosyl 1-pyrophosphate
alpha-D-5-Phosphoribosyl 1-pyrophosphoric acid
Alpha-D-5-PhosphoribosylPP
Alpha-D-Ribofuranose 5-phosphate 1-pyrophosphate
alpha-D-Ribofuranose 5-phosphoric acid 1-pyrophosphoric acid
Alpha-D-Ribofuranose, 5-(dihydrogen phosphate) 1-(trihydrogen diphosphate)
alpha-D-Ribofuranose, 5-(dihydrogen phosphoric acid) 1-(trihydrogen diphosphoric acid)
Alpha-delta-5-(Dihydrogen phosphate) 1-(trihydrogen pyrophosphate) Ribofuranose
alpha-delta-5-(Dihydrogen phosphoric acid) 1-(trihydrogen pyrophosphoric acid) ribofuranose
Alpha-delta-5-Phosphoribosyl 1-pyrophosphate
alpha-delta-5-Phosphoribosyl 1-pyrophosphoric acid
Alpha-delta-Ribofuranose 5-phosphate 1-pyrophosphate
alpha-delta-Ribofuranose 5-phosphoric acid 1-pyrophosphoric acid
Phosphoribosyl pyrophosphate
Phosphoribosyl pyrophosphoric acid
Phosphoribosyl-1-pyrophosphate
Phosphoribosyl-1-pyrophosphoric acid
Phosphoribosyl-pyrophosphate
Phosphoribosyl-pyrophosphoric acid
Phosphoribosylpyrophosphate
Phosphoribosylpyrophosphorate
Phosphoribosylpyrophosphoric acid
PP-Ribose-P
PRib-PP
PRPP
α-D-5-(Dihydrogen phosphate) 1-(trihydrogen pyrophosphate) ribofuranose
α-D-5-(Dihydrogen phosphoric acid) 1-(trihydrogen pyrophosphoric acid) ribofuranose
α-D-5-P-RibosylPP
α-D-5-Phosphoribosyl 1-pyrophosphate
α-D-5-Phosphoribosyl 1-pyrophosphoric acid
α-D-5-PhosphoribosylPP
α-D-Ribofuranose 5-phosphate 1-pyrophosphate
α-D-Ribofuranose 5-phosphoric acid 1-pyrophosphoric acid
α-D-Ribofuranose, 5-(dihydrogen phosphate) 1-(trihydrogen diphosphate)
α-D-Ribofuranose, 5-(dihydrogen phosphoric acid) 1-(trihydrogen diphosphoric acid)
α-δ-5-(Dihydrogen phosphate) 1-(trihydrogen pyrophosphate) ribofuranose
α-δ-5-(Dihydrogen phosphoric acid) 1-(trihydrogen pyrophosphoric acid) ribofuranose
α-δ-5-Phosphoribosyl 1-pyrophosphate
α-δ-5-Phosphoribosyl 1-pyrophosphoric acid
α-δ-Ribofuranose 5-phosphate 1-pyrophosphate
α-δ-Ribofuranose 5-phosphoric acid 1-pyrophosphoric acid

Chemical Formula:

C₅H₁₃O₁₄P₃

Weight:

Average: 390.0696
Monoisotopic: 389.95181466

InChI Key:

PQGCEDQWHSBAJP-TXICZTDVSA-N

InChI:

InChI=1S/C5H13O14P3/c6-3-2(1-16-20(8,9)10)17-5(4(3)7)18-22(14,15)19-21(11,12)13/h2-7H,1H2,(H,14,15)(H2,8,9,10)(H2,11,12,13)/t2-,3-,4-,5-/m1/s1

CAS number:

7540-64-9

IUPAC Name:

[({[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]oxy}(hydroxy)phosphoryl)oxy]phosphonic acid

Traditional IUPAC Name:

phosphoribosylpyrophosphate

SMILES:

O[C@H]1[C@@H](O)[C@@H](O[P@](O)(=O)OP(O)(O)=O)O[C@@H]1COP(O)(O)=O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Pentose phosphates

Alternative Parents

Substituents

Pentose phosphate
Pentose-5-phosphate
Monosaccharide phosphate
Organic pyrophosphate
Monoalkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Tetrahydrofuran
1,2-diol
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Alcohol
Hydrocarbon derivative
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

5-O-phosphono-D-ribofuranosyl diphosphate (CHEBI:17111 )

Physical Properties

State:

Solid

Charge:

-4

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	11.6 g/L	ALOGPS
logP	-0.74	ALOGPS
logP	-3	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	1.09	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	229.74 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	62.58 m³·mol⁻¹	ChemAxon
Polarizability	27.46 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

More...

SMPDB Pathways:

NAD biosynthesis	PW000829
NAD salvage	PW000830
PRPP Biosynthesis	PW000909
Pyrimidine metabolism	PW000942
Secondary Metabolites: Histidine biosynthesis	PW000984
Thiamin diphosphate biosynthesis	PW002028
Tryptophan metabolism	PW000815
adenine and adenosine salvage I	PW002069
adenine and adenosine salvage III	PW002072
guanine and guanosine salvage	PW002074
histidine biosynthesis	PW000810
purine nucleotides de novo biosynthesis	PW000910
purine nucleotides de novo biosynthesis 1435709748	PW000960
purine nucleotides de novo biosynthesis 2	PW002033
purine ribonucleosides degradation	PW002076
tryptophan metabolism II	PW001916

KEGG Pathways:

Alanine, aspartate and glutamate metabolism ec00250
Drug metabolism - other enzymes ec00983
Histidine metabolism ec00340
Metabolic pathways eco01100
Microbial metabolism in diverse environments ec01120
Nicotinate and nicotinamide metabolism ec00760
Pentose phosphate pathway ec00030
Phenylalanine, tyrosine and tryptophan biosynthesis ec00400
Purine metabolism ec00230
Pyrimidine metabolism ec00240
Tryptophan metabolism ec00380

EcoCyc Pathways:

5-aminoimidazole ribonucleotide biosynthesis I PWY-6121
5-aminoimidazole ribonucleotide biosynthesis II PWY-6122
NAD biosynthesis I (from aspartate) PYRIDNUCSYN-PWY
NAD salvage pathway I PYRIDNUCSAL-PWY
PRPP biosynthesis I PWY0-662
PRPP biosynthesis II PWY0-661
adenine and adenosine salvage II PWY-6605
adenine and adenosine salvage III PWY-6609
guanine and guanosine salvage I PWY-6620
histidine biosynthesis HISTSYN-PWY
salvage pathways of pyrimidine ribonucleotides PWY0-163
superpathway of 5-aminoimidazole ribonucleotide biosynthesis PWY-6277
tryptophan biosynthesis TRPSYN-PWY
uridine-5'-phosphate biosynthesis PWY-5686
xanthine and xanthosine salvage SALVPURINE2-PWY

Concentrations

Concentration	Strain	Media	Growth Status	Growth System	Temperature	Details
258± 0 uM	K12 NCM3722	Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucose	Mid-Log Phase	Shake flask and filter culture	37 oC	PMID: 19561621
153± 0 uM	K12 NCM3722	Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glycerol	Mid-Log Phase	Shake flask and filter culture	37 oC	PMID: 19561621
94± 0 uM	K12 NCM3722	Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L acetate	Mid-Log Phase	Shake flask and filter culture	37 oC	PMID: 19561621

Find out more about how we convert literature concentrations.

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-004j-7902000000-513a0a03122b76d768d9	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-004i-6952010000-eac4b7259ac1081ff665	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_5) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, negative	splash10-000i-0009000000-4d49c2b254fa550d7fc4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 8V, negative	splash10-000i-0129000000-1d706d02a4abbeb42ed5	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 11V, negative	splash10-004u-0987000000-ea0ae1567abd90f10399	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 14V, negative	splash10-004l-0961000000-703b20987f54fa234a79	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 19V, negative	splash10-004i-1930000000-0b45299b5f0eae24d372	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 24V, negative	splash10-004i-2910000000-9ce95a1b1c6b6ca5768d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 28V, negative	splash10-004i-6900000000-98e568c985ce119eab97	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 32V, negative	splash10-004i-9600000000-4d4d3c26cf4221488cb8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 38V, negative	splash10-004i-9300000000-ae7ce84c85a837e48257	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 45V, negative	splash10-004i-9100000000-535b36bb64043a2b5e66	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 54V, negative	splash10-004i-9000000000-b83900fdd755592d555a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 27V, negative	splash10-0006-0190000000-535b5f43d315fbc182ad	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 27V, negative	splash10-004i-9000000000-46d4cee1b5ac630ba9b8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 27V, negative	splash10-0a4i-0900000000-8f51c8c38a697fb3a6f0	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 27V, negative	splash10-006x-0930000000-6eebf2cc9471f692be90	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 27V, negative	splash10-01t9-7900000000-a94c6a883f36818a0855	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 27V, positive	splash10-00di-0089000000-73b944f3bcd8c2e5fa58	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 27V, positive	splash10-0udi-0079300000-a94093288821d386ab6a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, positive	splash10-0a4i-0001900000-04d2c9666f93d8bb3ec0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01tc-2934000000-e0fcfd13254fd3781439	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03dm-6593000000-b295e74d43b0dc625e47	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01r2-7920000000-a021603f22f19c083511	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0509000000-54231bd8f000ab2dd4a0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9301000000-447b996f7510c6ae354b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-54f70df2270a3e4f67d2	View in MoNA
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Becker MA, Losman MJ, Itkin P, Simkin PA: Gout with superactive phosphoribosylpyrophosphate synthetase due to increased enzyme catalytic rate. J Lab Clin Med. 1982 Apr;99(4):495-511. Pubmed: 6174658
Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
Blinov MN, Kamyshentsev MV, Luganova IS, Filanovskaia LI, Filippova VN: [Phosphoribosyl pyrophosphate and its metabolic enzymes in the erythrocytes in certain forms of anemia] Vopr Med Khim. 1976 Jul-Aug;22(4):456-62. Pubmed: 194412
Emmerson BT, Gordon RB, Thompson L: Adenine phosphoribosyltransferase deficiency: its inheritance and occurrence in a female with gout and renal disease. Aust N Z J Med. 1975 Oct;5(5):440-6. Pubmed: 1061547
Ghitis J, Schreiber C, Waxman S: Phosphate-induced phosphoribosylpyrophosphate elevations to assess deranged folate and purine nucleotide metabolism. Proc Soc Exp Biol Med. 1987 Oct;186(1):90-5. Pubmed: 2442765
Gorbach ZV: [Determination of phosphoribosyl pyrophosphate in the erythrocytes] Lab Delo. 1977;(12):724-5. Pubmed: 75318
Gordon RB, Keough DT, Emmerson BT: HPRT-deficiency associated with normal PRPP concentration and APRT activity. J Inherit Metab Dis. 1987;10(1):82-8. Pubmed: 2437388
Kane MA, Roth E, Raptis G, Schreiber C, Waxman S: Effect of intracellular folate concentration on the modulation of 5-fluorouracil cytotoxicity by the elevation of phosphoribosylpyrophosphate in cultured human KB cells. Cancer Res. 1987 Dec 15;47(24 Pt 1):6444-50. Pubmed: 2445472
Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Lachant NA, Zerez CR, Tanaka KR: Pyrimidine nucleotides impair phosphoribosylpyrophosphate (PRPP) synthetase subunit aggregation by sequestering magnesium. A mechanism for the decreased PRPP synthetase activity in hereditary erythrocyte pyrimidine 5'-nucleotidase deficiency. Biochim Biophys Acta. 1989 Jan 19;994(1):81-8. Pubmed: 2535789
MacDermot KD, Allsop J, Watts RW: The rate of purine synthesis de nova in blood mononuclear cells in vitro from patients with familial hyperuricaemic nephropathy. Clin Sci (Lond). 1984 Aug;67(2):249-58. Pubmed: 6744792
Marcolongo R, Pompucci G, Micheli V: Familial distribution of increased erythrocyte PP-ribose-P levels. Adv Exp Med Biol. 1977;76A:280-6. Pubmed: 193371
Micheli V, Taddeo A: [Spectrophotometric assay of 5-phosphoribosyl-1-pyrophosphate synthetase (PRPP) in erythrocyte lysate (author's transl)] Quad Sclavo Diagn. 1981 Jun;17(2):209-15. Pubmed: 6267652
Nishida Y, Akaoka I, Nishizawa T, Maruki M, Maruki K: Synthesis and concentration of 5-phosphoribosyl-1-pyrophosphate in erythrocytes from patients with Down's syndrome. Ann Rheum Dis. 1977 Jun;36(3):261-3. Pubmed: 141914
Rylance HJ, Wallace RC, Nuki G: A method for the determination of 5-phosphoribosyl 1-pyrophosphate concentrations in erythrocytes using high-performance liquid chromatography. Anal Biochem. 1987 Feb 1;160(2):337-41. Pubmed: 2437821
Sakuma R, Nishina T, Yamanaka H, Kamatani N, Nishioka K, Maeda M, Tsuji A: Phosphoribosylpyrophosphate synthetase in human erythrocytes: assay and kinetic studies using high-performance liquid chromatography. Clin Chim Acta. 1991 Dec 16;203(2-3):143-52. Pubmed: 1663846
Snyder FF, Dyer C, Seegmiller JE, Goldblum RM, Mills GC, Schmalstieg FC: Substrate inhibition of adenosine phosphorylation in adenosine deaminase deficiency and adenosine-mediated inhibition of PP-ribose-P dependent nucleotide synthesis in hypoxanthine phosphoribosyltransferase deficient erythrocytes. J Inherit Metab Dis. 1988;11(2):174-83. Pubmed: 2459496
Sperling O, Boer P, Brosh S, Elazar E, Szeinberg A, de Vries A: Normal activity of metabolic pathways involved in the formation and utilization of phosphoribosylpyrophosphate in erythrocytes of patients with primary metabolic gout. Nutr Metab. 1975;18(4):217-23. Pubmed: 172821
Tax WJ, Veerkamp JH: A simple and sensitive method for estimating the concentration and synthesis of 5-phosphoribosyl 1-pyrophosphate in red blood cells. Clin Chim Acta. 1977 Jul 15;78(2):209-16. Pubmed: 195752
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Yamaoka T, Yano M, Kondo M, Sasaki H, Hino S, Katashima R, Moritani M, Itakura M: Feedback inhibition of amidophosphoribosyltransferase regulates the rate of cell growth via purine nucleotide, DNA, and protein syntheses. J Biol Chem. 2001 Jun 15;276(24):21285-91. Epub 2001 Apr 4. Pubmed: 11290738
Zerez CR, Lachant NA, Tanaka KR: Decreased erythrocyte phosphoribosylpyrophosphate synthetase activity and impaired formation in thalassemia minor: a mechanism for decreased adenine nucleotide content. J Lab Clin Med. 1989 Jul;114(1):43-50. Pubmed: 2544652
Zoref-Shani E, Feinstein S, Frishberg Y, Bromberg Y, Sperling O: Kelley-Seegmiller syndrome due to a unique variant of hypoxanthine-guanine phosphoribosyltransferase: reduced affinity for 5-phosphoribosyl-1-pyrophosphate manifested only at low, physiological substrate concentrations. Biochim Biophys Acta. 2000 Feb 21;1500(2):197-203. Pubmed: 10657589

Synthesis Reference:

Gross, Akiva; Abril, Obsidiana; Lewis, Jerome M.; Geresh, Shimona; Whitesides, George M. Practical synthesis of 5-phospho-D-ribosyl a-1-pyrophosphate (PRPP): enzymatic routes from ribose 5-phosphate or ribose. Journal of the American Chemical Society (

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	17111
HMDB ID	HMDB00280
Pubchem Compound ID	7339
Kegg ID	C00119
ChemSpider ID	7062
Wikipedia	Phosphoribosyl pyrophosphate
BioCyc ID	PRPP
EcoCyc ID	PRPP
Ligand Expo	PRP

Enzymes

Protein Details

1. Anthranilate synthase component II

General function:: Involved in anthranilate phosphoribosyltransferase activity
Specific function:: Chorismate + L-glutamine = anthranilate + pyruvate + L-glutamate
Gene Name:: trpD
Uniprot ID:: P00904
Molecular weight:: 56869

Reactions

Chorismate + L-glutamine = anthranilate + pyruvate + L-glutamate.
N-(5-phospho-D-ribosyl)-anthranilate + diphosphate = anthranilate + 5-phospho-alpha-D-ribose 1-diphosphate.

Protein Details

2. Ribose-phosphate pyrophosphokinase

General function:: Involved in magnesium ion binding
Specific function:: ATP + D-ribose 5-phosphate = AMP + 5-phospho- alpha-D-ribose 1-diphosphate
Gene Name:: prs
Uniprot ID:: P0A717
Molecular weight:: 34218

Reactions

ATP + D-ribose 5-phosphate = AMP + 5-phospho-alpha-D-ribose 1-diphosphate.

Protein Details

3. Orotate phosphoribosyltransferase

General function:: Involved in orotate phosphoribosyltransferase activity
Specific function:: Catalyzes the transfer of a ribosyl phosphate group from 5-phosphoribose 1-diphosphate to orotate, leading to the formation of orotidine monophosphate (OMP)
Gene Name:: pyrE
Uniprot ID:: P0A7E3
Molecular weight:: 23567

Reactions

Orotidine 5'-phosphate + diphosphate = orotate + 5-phospho-alpha-D-ribose 1-diphosphate.

Protein Details

4. Uracil phosphoribosyltransferase

General function:: Involved in nucleoside metabolic process
Specific function:: Catalyzes the conversion of uracil and 5-phospho-alpha- D-ribose 1-diphosphate (PRPP) to UMP and diphosphate
Gene Name:: upp
Uniprot ID:: P0A8F0
Molecular weight:: 22533

Reactions

UMP + diphosphate = uracil + 5-phospho-alpha-D-ribose 1-diphosphate.

Protein Details

5. Hypoxanthine phosphoribosyltransferase

General function:: Involved in hypoxanthine phosphoribosyltransferase activity
Specific function:: This enzyme acts exclusively on hypoxanthine; it does not act on guanine
Gene Name:: hpt
Uniprot ID:: P0A9M2
Molecular weight:: 20115

Reactions

IMP + diphosphate = hypoxanthine + 5-phospho-alpha-D-ribose 1-diphosphate.

Protein Details

6. Xanthine phosphoribosyltransferase

General function:: Involved in nucleoside metabolic process
Specific function:: Acts on guanine, xanthine and to a lesser extent hypoxanthine
Gene Name:: gpt
Uniprot ID:: P0A9M5
Molecular weight:: 16971

Reactions

XMP + diphosphate = 5-phospho-alpha-D-ribose 1-diphosphate + xanthine.

Protein Details

7. Amidophosphoribosyltransferase

General function:: Involved in amidophosphoribosyltransferase activity
Specific function:: 5-phospho-beta-D-ribosylamine + diphosphate + L-glutamate = L-glutamine + 5-phospho-alpha-D-ribose 1-diphosphate + H(2)O
Gene Name:: purF
Uniprot ID:: P0AG16
Molecular weight:: 56488

Reactions

5-phospho-beta-D-ribosylamine + diphosphate + L-glutamate = L-glutamine + 5-phospho-alpha-D-ribose 1-diphosphate + H(2)O.

Protein Details

8. ATP-binding protein phnN

General function:: Involved in protein binding
Specific function:: Belongs to an operon involved in alkylphosphonate uptake and C-P lyase. Exact function not known
Gene Name:: phnN
Uniprot ID:: P16690
Molecular weight:: 20729

Reactions

ATP + ribose 1,5-bisphosphate = ADP + 5-phospho-alpha-D-ribose 1-diphosphate.

Protein Details

9. Nicotinate phosphoribosyltransferase

General function:: Involved in nicotinate phosphoribosyltransferase activity
Specific function:: Nicotinate D-ribonucleotide + diphosphate = nicotinate + 5-phospho-alpha-D-ribose 1-diphosphate
Gene Name:: pncB
Uniprot ID:: P18133
Molecular weight:: 45897

Reactions

Beta-nicotinate D-ribonucleotide + diphosphate = nicotinate + 5-phospho-alpha-D-ribose 1-diphosphate.

Protein Details

10. Nicotinate-nucleotide pyrophosphorylase [carboxylating]

General function:: Involved in catalytic activity
Specific function:: Involved in the catabolism of quinolinic acid (QA)
Gene Name:: nadC
Uniprot ID:: P30011
Molecular weight:: 32762

Reactions

Beta-nicotinate D-ribonucleotide + diphosphate + CO(2) = pyridine-2,3-dicarboxylate + 5-phospho-alpha-D-ribose 1-diphosphate.

Protein Details

11. ATP phosphoribosyltransferase

General function:: Involved in ATP phosphoribosyltransferase activity
Specific function:: Catalyzes the condensation of ATP and 5-phosphoribose 1- diphosphate to form N'-(5'-phosphoribosyl)-ATP (PR-ATP). Has a crucial role in the pathway because the rate of histidine biosynthesis seems to be controlled primarily by regulation of hisG enzymatic activity
Gene Name:: hisG
Uniprot ID:: P60757
Molecular weight:: 33366

Reactions

1-(5-phospho-D-ribosyl)-ATP + diphosphate = ATP + 5-phospho-alpha-D-ribose 1-diphosphate.

Protein Details

12. Adenine phosphoribosyltransferase

General function:: Involved in adenine phosphoribosyltransferase activity
Specific function:: Catalyzes a salvage reaction resulting in the formation of AMP, that is energically less costly than de novo synthesis
Gene Name:: apt
Uniprot ID:: P69503
Molecular weight:: 19859

Reactions

AMP + diphosphate = adenine + 5-phospho-alpha-D-ribose 1-diphosphate.

Phosphoribosyl pyrophosphate (ECMDB00280) (M2MDB000115)

Structure for #<Compound:0xa98df938>

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions