Carboxylic PRPP

Identification

Name
Carboxylic PRPP
Accession Number
DB03942  (EXPT02523)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • CPRPP
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 388.0968
Monoisotopic: 387.972550102
Chemical Formula
C6H15O13P3
InChI Key
OICBXEWBKALHHB-MOJAZDJTSA-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+/m1/s1
IUPAC Name
[({[(1S,2R,3R,4R)-2,3-dihydroxy-4-[(phosphonooxy)methyl]cyclopentyl]oxy}(hydroxy)phosphoryl)oxy]phosphonic acid
SMILES
[H][[email protected]]1(O)[[email protected]@]([H])(O)[[email protected]]([H])(C[[email protected]]1([H])COP(O)(O)=O)OP(O)(=O)OP(O)(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UPur operon repressorNot AvailableBacillus subtilis (strain 168)
UXanthine phosphoribosyltransferaseNot AvailableEscherichia coli (strain K12)
UAmidophosphoribosyltransferaseNot AvailableEscherichia coli (strain K12)
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
444189
PubChem Substance
46506729
ChemSpider
392181
HET
PCP
PDB Entries
1a95 / 1a96 / 1ecc / 1p4a / 1yte / 2i14

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not 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
Polarizability28.35 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organic oxoanionic compounds
Sub Class
Organic pyrophosphates
Direct Parent
Organic pyrophosphates
Alternative Parents
Monoalkyl phosphates / Cyclopentanols / Cyclitols and derivatives / 1,2-diols / Organic oxides / Hydrocarbon derivatives
Substituents
Organic pyrophosphate / Monoalkyl phosphate / Alkyl phosphate / Phosphoric acid ester / Organic phosphoric acid derivative / Cyclopentanol / Cyclitol or derivatives / Cyclic alcohol / Secondary alcohol / 1,2-diol
Molecular Framework
Aliphatic homomonocyclic compounds
External Descriptors
Not 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
Uniprot Name
Pur operon repressor
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
Uniprot Name
Xanthine phosphoribosyltransferase
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
Uniprot Name
Amidophosphoribosyltransferase
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]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 15:21