Record Information
Version1.0
Creation date2011-09-21 00:05:22 UTC
Update date2024-11-29 22:26:08 UTC
Primary IDFDB021928
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePhosphoribosyl pyrophosphate
DescriptionPhosphoribosyl pyrophosphate, also known as PRPP or prib-PP, 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. Phosphoribosyl pyrophosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). Phosphoribosyl pyrophosphate exists in all living species, ranging from bacteria to humans. Within humans, phosphoribosyl pyrophosphate participates in a number of enzymatic reactions. In particular, guanine and phosphoribosyl pyrophosphate can be biosynthesized from guanosine monophosphate; which is catalyzed by the enzyme adenine phosphoribosyltransferase. In addition, guanine and phosphoribosyl pyrophosphate can be biosynthesized from guanosine monophosphate through its interaction with the enzyme hypoxanthine-guanine phosphoribosyltransferase. In humans, phosphoribosyl pyrophosphate is involved in the metabolic disorder called the gout or kelley-seegmiller syndrome pathway. A derivative of alpha-D-ribose having a phosphate group at the 5-position and a diphosphate at the 1-position.
CAS Number7540-64-9
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility11.6 g/LALOGPS
logP-0.74ALOGPS
logP-3ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)1.09ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area229.74 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity62.58 m³·mol⁻¹ChemAxon
Polarizability27.46 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC5H13O14P3
IUPAC name[({[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]oxy}(hydroxy)phosphoryl)oxy]phosphonic acid
InChI IdentifierInChI=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
InChI KeyPQGCEDQWHSBAJP-TXICZTDVSA-N
Isomeric SMILESO[C@H]1[C@@H](O)[C@@H](O[P@](O)(=O)OP(O)(O)=O)O[C@@H]1COP(O)(O)=O
Average Molecular Weight390.0696
Monoisotopic Molecular Weight389.95181466
Classification
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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPentose 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 FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSPhosphoribosyl pyrophosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004j-7902000000-513a0a03122b76d768d9Spectrum
Predicted GC-MSPhosphoribosyl pyrophosphate, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004i-6952010000-eac4b7259ac1081ff665Spectrum
Predicted GC-MSPhosphoribosyl pyrophosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPhosphoribosyl pyrophosphate, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPhosphoribosyl pyrophosphate, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPhosphoribosyl pyrophosphate, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPhosphoribosyl pyrophosphate, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPhosphoribosyl pyrophosphate, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPhosphoribosyl pyrophosphate, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPhosphoribosyl pyrophosphate, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPhosphoribosyl pyrophosphate, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPhosphoribosyl pyrophosphate, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPhosphoribosyl pyrophosphate, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPhosphoribosyl pyrophosphate, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPhosphoribosyl pyrophosphate, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPhosphoribosyl pyrophosphate, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPhosphoribosyl pyrophosphate, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPhosphoribosyl pyrophosphate, TMS_2_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPhosphoribosyl pyrophosphate, TMS_2_11, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPhosphoribosyl pyrophosphate, TMS_2_12, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPhosphoribosyl pyrophosphate, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPhosphoribosyl pyrophosphate, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPhosphoribosyl pyrophosphate, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPhosphoribosyl pyrophosphate, TBDMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPhosphoribosyl pyrophosphate, TBDMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, negativesplash10-000i-0009000000-4d49c2b254fa550d7fc42020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 8V, negativesplash10-000i-0129000000-1d706d02a4abbeb42ed52020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 11V, negativesplash10-004u-0987000000-ea0ae1567abd90f103992020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 14V, negativesplash10-004l-0961000000-703b20987f54fa234a792020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 19V, negativesplash10-004i-1930000000-0b45299b5f0eae24d3722020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 24V, negativesplash10-004i-2910000000-9ce95a1b1c6b6ca5768d2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 28V, negativesplash10-004i-6900000000-98e568c985ce119eab972020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 32V, negativesplash10-004i-9600000000-4d4d3c26cf4221488cb82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 38V, negativesplash10-004i-9300000000-ae7ce84c85a837e482572020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 45V, negativesplash10-004i-9100000000-535b36bb64043a2b5e662020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 54V, negativesplash10-004i-9000000000-b83900fdd755592d555a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 27V, negativesplash10-0006-0190000000-535b5f43d315fbc182ad2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 27V, negativesplash10-004i-9000000000-46d4cee1b5ac630ba9b82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 27V, negativesplash10-0a4i-0900000000-8f51c8c38a697fb3a6f02020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 27V, negativesplash10-006x-0930000000-6eebf2cc9471f692be902020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 27V, negativesplash10-01t9-7900000000-a94c6a883f36818a08552020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 27V, positivesplash10-00di-0089000000-73b944f3bcd8c2e5fa582020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 27V, positivesplash10-0udi-0079300000-a94093288821d386ab6a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-0a4i-0001900000-04d2c9666f93d8bb3ec02020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01tc-2934000000-e0fcfd13254fd37814392015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dm-6593000000-b295e74d43b0dc625e472015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01r2-7920000000-a021603f22f19c0835112015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0509000000-54231bd8f000ab2dd4a02015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9301000000-447b996f7510c6ae354b2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-54f70df2270a3e4f67d22015-09-15View Spectrum
NMRNot Available
ChemSpider ID7062
ChEMBL IDNot Available
KEGG Compound IDC00119
Pubchem Compound ID7339
Pubchem Substance IDNot Available
ChEBI ID17111
Phenol-Explorer IDNot Available
DrugBank IDDB01632
HMDB IDHMDB00280
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID33926
KNApSAcK IDNot Available
HET IDPRP
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDPhosphoribosyl pyrophosphate
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
Pathways
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference