You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
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
SynonymLanguageCode
5-Phospho-alpha-D-ribose 1-diphosphateNot AvailableNot Available
5-Phosphoribosyl 1-pyrophosphateNot AvailableNot Available
5-PHOSPHORYLRIBOSE-1-PYROPHOSPHATENot AvailableNot Available
PhosphoribosylpyrophosphateNot AvailableNot Available
Ribofuranose, 5-phosphate 1-pyrophosphateNot AvailableNot Available
SaltsNot Available
Brand names
NameCompany
5-Phosphoribosyl diphosphateNot Available
Phosphoribosyl pyrophosphateNot Available
PRPNot Available
PRPPNot Available
Brand mixturesNot Available
CategoriesNot 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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassOrganooxygen Compounds
ClassCarbohydrates and Carbohydrate Conjugates
SubclassMonosaccharides
Direct parentPentose Phosphates
Alternative parentsOrganic Pyrophosphates; Monosaccharide Phosphates; Organic Phosphoric Acids; Organophosphate Esters; Tetrahydrofurans; Oxolanes; Secondary Alcohols; 1,2-Diols; Ethers; Polyamines
Substituentsorganic pyrophosphate; monosaccharide phosphate; phosphoric acid ester; organic phosphate; tetrahydrofuran; oxolane; 1,2-diol; secondary alcohol; polyamine; ether; alcohol
Classification descriptionThis compound belongs to the pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption - 0.9864
Blood Brain Barrier + 0.924
Caco-2 permeable - 0.7323
P-glycoprotein substrate Non-substrate 0.7206
P-glycoprotein inhibitor I Non-inhibitor 0.8258
P-glycoprotein inhibitor II Non-inhibitor 0.9919
Renal organic cation transporter Non-inhibitor 0.9101
CYP450 2C9 substrate Non-substrate 0.8024
CYP450 2D6 substrate Non-substrate 0.8346
CYP450 3A4 substrate Non-substrate 0.5843
CYP450 1A2 substrate Non-inhibitor 0.8892
CYP450 2C9 substrate Non-inhibitor 0.886
CYP450 2D6 substrate Non-inhibitor 0.9188
CYP450 2C19 substrate Non-inhibitor 0.8792
CYP450 3A4 substrate Non-inhibitor 0.9727
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9715
Ames test Non AMES toxic 0.7781
Carcinogenicity Non-carcinogens 0.9024
Biodegradation Ready biodegradable 0.7128
Rat acute toxicity 2.0708 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.923
hERG inhibition (predictor II) Non-inhibitor 0.8905
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
water solubility1.16e+01 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 area229.74ChemAxon
rotatable bond count7ChemAxon
refractivity62.58ChemAxon
polarizability27.45ChemAxon
number of rings1ChemAxon
bioavailability0ChemAxon
rule of fiveNoChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
PubChem Compound7339
PubChem Substance46506467
ChemSpider1012
BindingDB25315
ChEBI17111
ChEMBL
HETPRP
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Hypoxanthine-guanine phosphoribosyltransferase

Kind: protein

Organism: Trypanosoma cruzi

Pharmacological action: unknown

Components

Name UniProt ID Details
Hypoxanthine-guanine phosphoribosyltransferase Q27796 Details

2. Adenine phosphoribosyltransferase

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Adenine phosphoribosyltransferase P07741 Details

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

3. Anthranilate phosphoribosyltransferase

Kind: protein

Organism: Erwinia carotovora

Pharmacological action: unknown

Components

Name UniProt ID Details
Anthranilate phosphoribosyltransferase Q8VP84 Details

4. Hypoxanthine-guanine phosphoribosyltransferase

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Hypoxanthine-guanine phosphoribosyltransferase P00492 Details

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
  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
  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

5. Orotate phosphoribosyltransferase

Kind: protein

Organism: Salmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)

Pharmacological action: unknown

Components

Name UniProt ID Details
Orotate phosphoribosyltransferase P08870 Details

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
  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

6. Uridine-cytidine kinase-like 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Uridine-cytidine kinase-like 1 Q9NWZ5 Details

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
  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
  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

Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:15