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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
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
5-Phosphoribosyl diphosphateNot Available
Phosphoribosyl pyrophosphateNot Available
PRPNot Available
PRPPNot Available
Brand mixturesNot Available
SaltsNot 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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassMonosaccharides
Direct ParentMonosaccharide phosphates
Alternative Parents
Substituents
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Oxolane
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrateNon-inhibitor0.886
CYP450 2D6 substrateNon-inhibitor0.9188
CYP450 2C19 substrateNon-inhibitor0.8792
CYP450 3A4 substrateNon-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
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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
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: 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

2. 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

3. 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

4. Hypoxanthine-guanine phosphoribosyltransferase

Kind: protein

Organism: Trypanosoma cruzi

Pharmacological action: unknown

Components

Name UniProt ID Details
Hypoxanthine-guanine phosphoribosyltransferase Q27796 Details

5. 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

6. Anthranilate phosphoribosyltransferase

Kind: protein

Organism: Erwinia carotovora

Pharmacological action: unknown

Components

Name UniProt ID Details
Anthranilate phosphoribosyltransferase Q8VP84 Details
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:15