Identification
NameAlpha-Phosphoribosylpyrophosphoric Acid
Accession NumberDB01632  (EXPT02663)
TypeSmall Molecule
GroupsExperimental
Description

The key substance in the biosynthesis of histidine, tryptophan, and purine and pyrimidine nucleotides.

Structure
Thumb
Synonyms
5-Phospho-alpha-D-ribose 1-diphosphate
5-Phosphoribosyl 1-pyrophosphate
5-PHOSPHORYLRIBOSE-1-PYROPHOSPHATE
Phosphoribosylpyrophosphate
Ribofuranose, 5-phosphate 1-pyrophosphate
External IDs Not Available
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
5-Phosphoribosyl diphosphateNot Available
Phosphoribosyl pyrophosphateNot Available
PRPNot Available
PRPPNot Available
Brand mixturesNot Available
CategoriesNot Available
UNIINot Available
CAS number13270-65-0
WeightAverage: 390.0696
Monoisotopic: 389.95181466
Chemical FormulaC5H13O14P3
InChI KeyPQGCEDQWHSBAJP-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
IUPAC Name
[({[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]oxy}(hydroxy)phosphoryl)oxy]phosphonic acid
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
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Hypoxanthine-guanine phosphoribosyltransferaseProteinunknownNot AvailableHumanP00492 details
Orotate phosphoribosyltransferaseProteinunknownNot AvailableSalmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)P08870 details
Uridine-cytidine kinase-like 1ProteinunknownNot AvailableHumanQ9NWZ5 details
Hypoxanthine-guanine phosphoribosyltransferaseProteinunknownNot AvailableTrypanosoma cruziQ27796 details
Adenine phosphoribosyltransferaseProteinunknownNot AvailableHumanP07741 details
Anthranilate phosphoribosyltransferaseProteinunknownNot AvailableErwinia carotovoraQ8VP84 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
Pathways
PathwayCategorySMPDB ID
Lesch-Nyhan Syndrome (LNS)DiseaseSMP00364
Myoadenylate deaminase deficiencyDiseaseSMP00537
Thioguanine Metabolism PathwayDrug metabolismSMP00647
Pyrimidine MetabolismMetabolicSMP00046
Adenylosuccinate Lyase DeficiencyDiseaseSMP00167
Molybdenum Cofactor DeficiencyDiseaseSMP00203
Purine Nucleoside Phosphorylase DeficiencyDiseaseSMP00210
Adenine phosphoribosyltransferase deficiency (APRT)DiseaseSMP00535
Mitochondrial DNA depletion syndromeDiseaseSMP00536
Pentose Phosphate PathwayMetabolicSMP00031
Gout or Kelley-Seegmiller SyndromeDiseaseSMP00365
Azathioprine Action PathwayDrug actionSMP00427
Xanthinuria type IIDiseaseSMP00513
Transaldolase deficiencyDiseaseSMP00520
Succinic semialdehyde dehydrogenase deficiencyDiseaseSMP00567
Mercaptopurine Metabolism PathwayDrug metabolismSMP00609
Purine MetabolismMetabolicSMP00050
Glutamate MetabolismMetabolicSMP00072
Adenosine Deaminase DeficiencyDiseaseSMP00144
Beta Ureidopropionase DeficiencyDiseaseSMP00172
Dihydropyrimidinase DeficiencyDiseaseSMP00178
UMP Synthase Deiciency (Orotic Aciduria)DiseaseSMP00219
Xanthine Dehydrogenase Deficiency (Xanthinuria)DiseaseSMP00220
HomocarnosinosisDiseaseSMP00385
Nicotinate and Nicotinamide MetabolismMetabolicSMP00048
2-Hydroxyglutric Aciduria (D And L Form)DiseaseSMP00136
AICA-RibosiduriaDiseaseSMP00168
MNGIE (Mitochondrial Neurogastrointestinal Encephalopathy)DiseaseSMP00202
4-Hydroxybutyric Aciduria/Succinic Semialdehyde Dehydrogenase DeficiencyDiseaseSMP00243
Hyperinsulinism-Hyperammonemia SyndromeDiseaseSMP00339
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
0Enrolling by InvitationTreatmentKnee Pain Chronic / Pes Anserinus Bursitis / Status-Post Total Knee Arthroplasty1
1Active Not RecruitingTreatmentBone Resorption1
1CompletedSupportive CareChronic Ulcer1
1CompletedTreatmentRotator Cuff Syndrome / Rotator Cuff Tendinitis / Shoulder Pain / Spinal Cord Injuries (SCI)1
1CompletedTreatmentTraumatic Bone Cyst1
1CompletedTreatmentSynovitis of osteoarthritis1
1Not Yet RecruitingTreatmentInterstitial Cystitis1
1TerminatedTreatmentRotator Cuff Syndrome1
1, 2CompletedTreatmentChronic Ulcer1
1, 2RecruitingTreatmentChronic Obstructive Pulmonary Disease (COPD)1
1, 2RecruitingTreatmentPrevious Incision / Scar; Previous Cesarean Section1
1, 2Unknown StatusTreatmentOsteoarthritis of the Knees1
2Active Not RecruitingTreatmentLateral Epicondylitis1
2Active Not RecruitingTreatmentOsteoarthritis of the Knees1
2CompletedPreventionHaemophilus Infections / Haemophilus Influenzae Type B / Meningococcal Infections / Neisseria Meningitidis1
2CompletedSupportive CareWound Healing, Adipose Tissue Extract, Plateelt Rich Plasma, Skin Graft Donor Site1
2CompletedTreatmentAcute Hamstring Muscle Strain Injury1
2Not Yet RecruitingSupportive CareUnilateral Cleft Lip1
2RecruitingTreatmentAsherman's Syndrome / Infertilities1
2RecruitingTreatmentEndometrial Disorder / Endometrial Thickness Not Growing Under Estrogen Stimulation / Thin Endometrium1
2RecruitingTreatmentOsteoarthritis of the Knees2
2RecruitingTreatmentSynovitis of osteoarthritis2
2, 3RecruitingPreventionPelvic Floor Disorders1
3Active Not RecruitingTreatmentUlcers1
3CompletedTreatmentArthroplasty, Replacement1
3CompletedTreatmentMuscle Injuries1
3CompletedTreatmentOsteoarthritis of the Knees1
3CompletedTreatmentSynovitis of osteoarthritis1
3RecruitingPreventionEndoscopic Mucosal Resection / Endoscopic Submucosal Dissection / Platelet-rich Plasma1
3RecruitingTreatmentOsteoarthritis, Hip1
3Unknown StatusTreatmentEye Dryness / Sjogren's Syndrome1
4Active Not RecruitingTreatmentPost Operative Pain1
4CompletedTreatmentKnee Chondropathy / Osteoarthritis of the Knees1
4RecruitingTreatmentBupivacaine / Chronic Low Back Pain (CLBP) / Injection Site / Lidocaine / Platelet / Platelet Rich Plasma / Sacroiliac; Backache / Sacroiliitis / Treatments / Ultrasound Therapy; Complications1
4RecruitingTreatmentFemoroacetabular Impingement1
4RecruitingTreatmentHip Pain / Tendinopathy1
4RecruitingTreatmentOsteoarthritis of the Knees1
4RecruitingTreatmentShoulder Pain / Synovitis of osteoarthritis1
4RecruitingTreatmentSynovitis of osteoarthritis1
4WithdrawnTreatmentRectal Fistulas1
Not AvailableActive Not RecruitingTreatmentKnee Chondropathy / Knee Early Osteoarthritis1
Not AvailableCompletedPreventionBlood Loss / Pain1
Not AvailableCompletedPreventionElective Foot and Ankle Surgery1
Not AvailableCompletedTreatmentAtrophic Scar1
Not AvailableCompletedTreatmentLateral Epicondylitis1
Not AvailableCompletedTreatmentOsteoarthritis of the Knees1
Not AvailableCompletedTreatmentPain1
Not AvailableCompletedTreatmentPeriorbital Hyperpigmentation1
Not AvailableCompletedTreatmentTendinopathy1
Not AvailableEnrolling by InvitationTreatmentChondral Lesions / Femoroacetabular Impingement1
Not AvailableEnrolling by InvitationTreatmentOsteoarthritis, Hip1
Not AvailableNot Yet RecruitingTreatmentCarious Teeth1
Not AvailableNot Yet RecruitingTreatmentOsteoarthritis Thumb1
Not AvailableNot Yet RecruitingTreatmentVitiligo1
Not AvailableRecruitingTreatmentDiabetic Peripheral Neuropathy (DPN)1
Not AvailableRecruitingTreatmentFracture Bone1
Not AvailableRecruitingTreatmentLichen Sclerosus of Vulva1
Not AvailableRecruitingTreatmentOsteoarthritis, Hip1
Not AvailableRecruitingTreatmentOsteochondritis Dissecans1
Not AvailableRecruitingTreatmentPatellar Tendinopathy1
Not AvailableRecruitingTreatmentPlantar fascial fibromatosis1
Not AvailableTerminatedTreatmentShoulder Impingement Syndrome1
Not AvailableUnknown StatusTreatmentAndrogenetic Alopecia1
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility11.6 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity62.58 m3·mol-1ChemAxon
Polarizability27.45 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9864
Blood Brain Barrier+0.924
Caco-2 permeable-0.7323
P-glycoprotein substrateNon-substrate0.7206
P-glycoprotein inhibitor INon-inhibitor0.8258
P-glycoprotein inhibitor IINon-inhibitor0.9919
Renal organic cation transporterNon-inhibitor0.9101
CYP450 2C9 substrateNon-substrate0.8024
CYP450 2D6 substrateNon-substrate0.8346
CYP450 3A4 substrateNon-substrate0.5843
CYP450 1A2 substrateNon-inhibitor0.8892
CYP450 2C9 inhibitorNon-inhibitor0.886
CYP450 2D6 inhibitorNon-inhibitor0.9188
CYP450 2C19 inhibitorNon-inhibitor0.8792
CYP450 3A4 inhibitorNon-inhibitor0.9727
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9715
Ames testNon AMES toxic0.7781
CarcinogenicityNon-carcinogens0.9024
BiodegradationReady biodegradable0.7128
Rat acute toxicity2.0708 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.923
hERG inhibition (predictor II)Non-inhibitor0.8905
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01tc-2934000000-e0fcfd13254fd3781439View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dm-6593000000-b295e74d43b0dc625e47View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01r2-7920000000-a021603f22f19c083511View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0509000000-54231bd8f000ab2dd4a0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9301000000-447b996f7510c6ae354bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-54f70df2270a3e4f67d2View in MoNA
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
Direct ParentPentose phosphates
Alternative ParentsOrganic pyrophosphates / Monosaccharide phosphates / Monoalkyl phosphates / Oxolanes / Secondary alcohols / 1,2-diols / Oxacyclic compounds / Organic oxides / Hydrocarbon derivatives
SubstituentsPentose phosphate / Pentose-5-phosphate / Monosaccharide phosphate / Organic pyrophosphate / Monoalkyl phosphate / Alkyl phosphate / Phosphoric acid ester / Organic phosphoric acid derivative / Oxolane / Secondary alcohol
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors5-O-phosphono-D-ribofuranosyl diphosphate (CHEBI:17111 )

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Protein homodimerization 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
Uniprot Name:
Hypoxanthine-guanine phosphoribosyltransferase
Molecular Weight:
24579.155 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Salmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)
Pharmacological action
unknown
General Function:
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:
P08870
Uniprot Name:
Orotate phosphoribosyltransferase
Molecular Weight:
23561.74 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Uridine kinase activity
Specific Function:
May contribute to UTP accumulation needed for blast transformation and proliferation.
Gene Name:
UCKL1
Uniprot ID:
Q9NWZ5
Uniprot Name:
Uridine-cytidine kinase-like 1
Molecular Weight:
61140.395 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Trypanosoma cruzi
Pharmacological action
unknown
General Function:
Hypoxanthine phosphoribosyltransferase activity
Specific Function:
Not Available
Gene Name:
HGPRTase
Uniprot ID:
Q27796
Uniprot Name:
Hypoxanthine-guanine phosphoribosyltransferase
Molecular Weight:
25529.02 Da
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Amp binding
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
Uniprot Name:
Adenine phosphoribosyltransferase
Molecular Weight:
19607.535 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Erwinia carotovora
Pharmacological action
unknown
General Function:
Magnesium ion binding
Specific Function:
Catalyzes the transfer of the phosphoribosyl group of 5-phosphorylribose-1-pyrophosphate (PRPP) to anthranilate to yield N-(5'-phosphoribosyl)-anthranilate (PRA).
Gene Name:
trpD
Uniprot ID:
Q8VP84
Uniprot Name:
Anthranilate phosphoribosyltransferase
Molecular Weight:
37017.84 Da
Drug created on June 13, 2005 07:24 / Updated on September 01, 2017 10:42