Record Information
Version1.0
Created at2020-04-17 18:41:47 UTC
Updated at2020-11-18 16:38:49 UTC
CannabisDB IDCDB004836
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common 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. Phosphoribosyl pyrophosphate is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
Synonyms
ValueSource
5-Phospho-alpha-D-ribose 1-diphosphateChEBI
5-Phosphoribosyl 1-pyrophosphateChEBI
5-Phosphoribosyl diphosphateChEBI
alpha-D-Ribofuranose 5-(dihydrogen phosphate) 1-(trihydrogen diphosphate)ChEBI
alpha-Phosphoribosylpyrophosphoric acidChEBI
PhosphoribosylpyrophosphateChEBI
PRib-PPChEBI
PRPPChEBI
5-Phospho-a-D-ribose 1-diphosphateGenerator
5-Phospho-a-D-ribose 1-diphosphoric acidGenerator
5-Phospho-alpha-D-ribose 1-diphosphoric acidGenerator
5-Phospho-α-D-ribose 1-diphosphateGenerator
5-Phospho-α-D-ribose 1-diphosphoric acidGenerator
Phosphoribosyl pyrophosphoric acidGenerator
5-Phosphoribosyl 1-pyrophosphoric acidGenerator
5-Phosphoribosyl diphosphoric acidGenerator
a-D-Ribofuranose 5-(dihydrogen phosphate) 1-(trihydrogen diphosphate)Generator
a-D-Ribofuranose 5-(dihydrogen phosphoric acid) 1-(trihydrogen diphosphoric acid)Generator
alpha-D-Ribofuranose 5-(dihydrogen phosphoric acid) 1-(trihydrogen diphosphoric acid)Generator
α-D-Ribofuranose 5-(dihydrogen phosphate) 1-(trihydrogen diphosphate)Generator
α-D-Ribofuranose 5-(dihydrogen phosphoric acid) 1-(trihydrogen diphosphoric acid)Generator
a-PhosphoribosylpyrophosphateGenerator
a-Phosphoribosylpyrophosphoric acidGenerator
alpha-PhosphoribosylpyrophosphateGenerator
α-PhosphoribosylpyrophosphateGenerator
α-Phosphoribosylpyrophosphoric acidGenerator
Phosphoribosylpyrophosphoric acidGenerator
5-Phospho-a-D-ribose-1-diphosphateHMDB
5-Phospho-a-D-ribosyl pyrophosphateHMDB
5-Phospho-alpha-D-ribose-1-diphosphateHMDB
5-Phospho-alpha-D-ribosyl pyrophosphateHMDB
5-Phosphoribose 1-pyrophosphateHMDB
5-Phosphoribosyl 1-diphosphateHMDB
5-Phosphoribosyl a-1-pyrophosphateHMDB
5-Phosphoribosyl-1-pyrophosphateHMDB
5-Phosphorylribose 1-a-diphosphateHMDB
5-Phosphorylribose 1-alpha-diphosphateHMDB
5-Phosphorylribose 1-pyrophosphateHMDB
5-Phosphorylribosyl 1-pyrophosphateHMDB
a-D-5-(Dihydrogen phosphate) 1-(trihydrogen pyrophosphate) ribofuranoseHMDB
a-D-5-Phosphoribosyl 1-pyrophosphateHMDB
a-D-Ribofuranose 5-phosphate 1-pyrophosphateHMDB
a-D-Ribofuranose, 5-(dihydrogen phosphate) 1-(trihydrogen diphosphate)HMDB
alpha-D-5-(Dihydrogen phosphate) 1-(trihydrogen pyrophosphate) ribofuranoseHMDB
alpha-D-5-Phosphoribosyl 1-pyrophosphateHMDB
alpha-D-Ribofuranose 5-phosphate 1-pyrophosphateHMDB
alpha-D-Ribofuranose, 5-(dihydrogen phosphate) 1-(trihydrogen diphosphate)HMDB
Phosphoribosyl-1-pyrophosphateHMDB
Phosphoribosyl-pyrophosphateHMDB
PhosphoribosylpyrophosphorateHMDB
PP-Ribose-PHMDB
Pyrophosphate, phosphoribosylMeSH, HMDB
5-Phospho-α-D-ribose-1-diphosphateHMDB
5-Phospho-α-D-ribosyl pyrophosphateHMDB
5-Phosphoribosyl alpha-1-pyrophosphateHMDB
5-Phosphoribosyl pyrophosphateHMDB
5-Phosphoribosyl α-1-pyrophosphateHMDB
5-Phosphorylribose 1-α-diphosphateHMDB
Phosphoribosyl pyrophosphateHMDB
α-D-5-Phosphoribosyl 1-pyrophosphateHMDB
Chemical FormulaC5H13O14P3
Average Molecular Weight390.07
Monoisotopic Molecular Weight389.9518
IUPAC Name[({[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]oxy}(hydroxy)phosphoryl)oxy]phosphonic acid
Traditional Namephosphoribosylpyrophosphate
CAS Registry Number7540-64-9
SMILES
O[C@H]1[C@@H](O)[C@@H](OP(O)(=O)OP(O)(O)=O)O[C@@H]1COP(O)(O)=O
InChI Identifier
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
InChI KeyPQGCEDQWHSBAJP-TXICZTDVSA-N
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.
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:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
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
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, negativesplash10-000i-0009000000-4d49c2b254fa550d7fc4Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 8V, negativesplash10-000i-0129000000-1d706d02a4abbeb42ed5Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 11V, negativesplash10-004u-0987000000-ea0ae1567abd90f10399Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 14V, negativesplash10-004l-0961000000-703b20987f54fa234a79Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 19V, negativesplash10-004i-1930000000-0b45299b5f0eae24d372Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 24V, negativesplash10-004i-2910000000-9ce95a1b1c6b6ca5768dSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 28V, negativesplash10-004i-6900000000-98e568c985ce119eab97Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 32V, negativesplash10-004i-9600000000-4d4d3c26cf4221488cb8Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 38V, negativesplash10-004i-9300000000-ae7ce84c85a837e48257Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 45V, negativesplash10-004i-9100000000-535b36bb64043a2b5e66Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 54V, negativesplash10-004i-9000000000-b83900fdd755592d555aSpectrum
MS/MSLC-MS/MS Spectrum - n/a 27V, negativesplash10-0006-0190000000-535b5f43d315fbc182adSpectrum
MS/MSLC-MS/MS Spectrum - n/a 27V, negativesplash10-004i-9000000000-46d4cee1b5ac630ba9b8Spectrum
MS/MSLC-MS/MS Spectrum - n/a 27V, negativesplash10-0a4i-0900000000-8f51c8c38a697fb3a6f0Spectrum
MS/MSLC-MS/MS Spectrum - n/a 27V, negativesplash10-006x-0930000000-6eebf2cc9471f692be90Spectrum
MS/MSLC-MS/MS Spectrum - n/a 27V, negativesplash10-01t9-7900000000-a94c6a883f36818a0855Spectrum
MS/MSLC-MS/MS Spectrum - n/a 27V, positivesplash10-00di-0089000000-73b944f3bcd8c2e5fa58Spectrum
MS/MSLC-MS/MS Spectrum - n/a 27V, positivesplash10-0udi-0079300000-a94093288821d386ab6aSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-0a4i-0001900000-04d2c9666f93d8bb3ec0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01tc-2934000000-e0fcfd13254fd3781439Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dm-6593000000-b295e74d43b0dc625e47Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01r2-7920000000-a021603f22f19c083511Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0509000000-54231bd8f000ab2dd4a0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9301000000-447b996f7510c6ae354bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-54f70df2270a3e4f67d2Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
AmidophosphoribosyltransferasePPAT4q12Q06203 details
Nicotinate-nucleotide pyrophosphorylase [carboxylating]QPRT16p11.2Q15274 details
Adenine phosphoribosyltransferaseAPRT16q24P07741 details
Hypoxanthine-guanine phosphoribosyltransferaseHPRT1Xq26.1P00492 details
Ribose-phosphate pyrophosphokinase 3PRPS1L17p21.1P21108 details
Ribose-phosphate pyrophosphokinase 1PRPS1Xq21.32-q24P60891 details
Ribose-phosphate pyrophosphokinase 2PRPS2Xp22.2P11908 details
Uridine 5'-monophosphate synthaseUMPS3q13P11172 details
Nicotinamide phosphoribosyltransferaseNAMPT7q22.3P43490 details
Nicotinate phosphoribosyltransferaseNAPRT18q24.3Q6XQN6 details
Uracil phosphoribosyltransferase homologUPRTQ96BW1 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
AmidophosphoribosyltransferasePPAT4q12Q06203 details
Ribose-phosphate pyrophosphokinase 3PRPS1L17p21.1P21108 details
Ribose-phosphate pyrophosphokinase 1PRPS1Xq21.32-q24P60891 details
Ribose-phosphate pyrophosphokinase 2PRPS2Xp22.2P11908 details
ReceptorsNot Available
Transcriptional Factors
Protein NameGene NameLocusUniprot IDDetails
Nicotinamide phosphoribosyltransferaseNAMPT7q22.3P43490 details
Concentrations Data
Not Available
HMDB IDHMDB0000280
DrugBank IDDB01632
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021928
KNApSAcK IDC00007296
Chemspider ID7062
KEGG Compound IDC00119
BioCyc IDPRPP
BiGG ID33926
Wikipedia LinkPhosphoribosyl pyrophosphate
METLIN ID5274
PubChem Compound7339
PDB IDNot Available
ChEBI ID17111
References
General ReferencesNot Available

Only showing the first 10 proteins. There are 16 proteins in total.

Enzymes

General function:
Involved in amidophosphoribosyltransferase activity
Specific function:
Not Available
Gene Name:
PPAT
Uniprot ID:
Q06203
Molecular weight:
57398.52
General function:
Involved in catalytic activity
Specific function:
Involved in the catabolism of quinolinic acid (QA).
Gene Name:
QPRT
Uniprot ID:
Q15274
Molecular weight:
30815.28
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:
APRT
Uniprot ID:
P07741
Molecular weight:
19607.535
General function:
Involved in hypoxanthine phosphoribosyltransferase activity
Specific function:
Converts guanine to guanosine monophosphate, and hypoxanthine to inosine monophosphate. Transfers the 5-phosphoribosyl group from 5-phosphoribosylpyrophosphate onto the purine. Plays a central role in the generation of purine nucleotides through the purine salvage pathway.
Gene Name:
HPRT1
Uniprot ID:
P00492
Molecular weight:
24579.155
General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the synthesis of phosphoribosylpyrophosphate (PRPP) that is essential for nucleotide synthesis.
Gene Name:
PRPS1L1
Uniprot ID:
P21108
Molecular weight:
34838.915
General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the synthesis of phosphoribosylpyrophosphate (PRPP) that is essential for nucleotide synthesis.
Gene Name:
PRPS1
Uniprot ID:
P60891
Molecular weight:
12324.195
General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the synthesis of phosphoribosylpyrophosphate (PRPP) that is essential for nucleotide synthesis.
Gene Name:
PRPS2
Uniprot ID:
P11908
Molecular weight:
35054.06
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
UMPS
Uniprot ID:
P11172
Molecular weight:
52221.075
General function:
Involved in nicotinate phosphoribosyltransferase activity
Specific function:
Catalyzes the condensation of nicotinamide with 5-phosphoribosyl-1-pyrophosphate to yield nicotinamide mononucleotide, an intermediate in the biosynthesis of NAD. It is the rate limiting component in the mammalian NAD biosynthesis pathway (By similarity).
Gene Name:
NAMPT
Uniprot ID:
P43490
Molecular weight:
55520.8
General function:
Involved in nicotinate phosphoribosyltransferase activity
Specific function:
Catalyzes the conversion of nicotinic acid (NA) to NA mononucleotide (NaMN). Essential for NA to increase cellular NAD levels and prevent oxidative stress of the cells.
Gene Name:
NAPRT1
Uniprot ID:
Q6XQN6
Molecular weight:
57577.575

Only showing the first 10 proteins. There are 16 proteins in total.