You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameCarboxylic PRPP
Accession NumberDB03942  (EXPT02523)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
Synonyms
CPRPP
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
UNIINot Available
CAS numberNot Available
WeightAverage: 388.0968
Monoisotopic: 387.972550102
Chemical FormulaC6H15O13P3
InChI KeyInChIKey=OICBXEWBKALHHB-FSIIMWSLSA-N
InChI
InChI=1S/C6H15O13P3/c7-5-3(2-17-20(9,10)11)1-4(6(5)8)18-22(15,16)19-21(12,13)14/h3-8H,1-2H2,(H,15,16)(H2,9,10,11)(H2,12,13,14)/t3-,4+,5-,6-/m0/s1
IUPAC Name
[({[(1R,2R,3S,4S)-2,3-dihydroxy-4-[(phosphonooxy)methyl]cyclopentyl]oxy}(hydroxy)phosphoryl)oxy]phosphonic acid
SMILES
O[C@@H]1[C@@H](O)[C@@H](C[[email protected]]1COP(O)(O)=O)O[P@](O)(=O)OP(O)(O)=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as organic pyrophosphates. These are organic compounds containing the pyrophosphate oxoanion, with the structure OP([O-])(=O)OP(O)([O-])=O.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassOrganic oxoanionic compounds
Sub ClassOrganic pyrophosphates
Direct ParentOrganic pyrophosphates
Alternative Parents
Substituents
  • Organic pyrophosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Cyclopentanol
  • Cyclic alcohol
  • Secondary alcohol
  • 1,2-diol
  • Hydrocarbon derivative
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9406
Blood Brain Barrier+0.9145
Caco-2 permeable-0.7289
P-glycoprotein substrateNon-substrate0.7376
P-glycoprotein inhibitor INon-inhibitor0.8101
P-glycoprotein inhibitor IINon-inhibitor0.9922
Renal organic cation transporterNon-inhibitor0.9131
CYP450 2C9 substrateNon-substrate0.8343
CYP450 2D6 substrateNon-substrate0.8387
CYP450 3A4 substrateNon-substrate0.566
CYP450 1A2 substrateNon-inhibitor0.8909
CYP450 2C9 inhibitorNon-inhibitor0.8869
CYP450 2D6 inhibitorNon-inhibitor0.9163
CYP450 2C19 inhibitorNon-inhibitor0.891
CYP450 3A4 inhibitorNon-inhibitor0.9742
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9801
Ames testNon AMES toxic0.7788
CarcinogenicityNon-carcinogens0.8422
BiodegradationReady biodegradable0.5231
Rat acute toxicity2.0804 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9257
hERG inhibition (predictor II)Non-inhibitor0.8884
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility13.1 mg/mLALOGPS
logP-0.83ALOGPS
logP-3ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)1.45ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area220.51 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity66.32 m3·mol-1ChemAxon
Polarizability28.55 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 ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Bacillus subtilis (strain 168)
Pharmacological action
unknown
General Function:
Dna binding
Specific Function:
Controls the transcription of the pur operon for purine biosynthetic genes, binds to the control region of the operon. DNA binding is inhibited by 5-phosphoribosyl 1-pyrophosphate.
Gene Name:
purR
Uniprot ID:
P37551
Molecular Weight:
31228.72 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
Escherichia coli (strain K12)
Pharmacological action
unknown
General Function:
Xanthine phosphoribosyltransferase activity
Specific Function:
Acts on guanine, xanthine and to a lesser extent hypoxanthine.
Gene Name:
gpt
Uniprot ID:
P0A9M5
Molecular Weight:
16970.455 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
Escherichia coli (strain K12)
Pharmacological action
unknown
General Function:
Transferase activity, transferring glycosyl groups
Specific Function:
Catalyzes the formation of phosphoribosylamine from phosphoribosylpyrophosphate (PRPP) and glutamine. Can also use NH(3) in place of glutamine.
Gene Name:
purF
Uniprot ID:
P0AG16
Molecular Weight:
56487.49 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 ]
Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23