1-(5-phospho-D-ribosyl)-ATP

Identification

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Name
1-(5-phospho-D-ribosyl)-ATP
Accession Number
DB01661  (EXPT02665)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • Phosphoribosyl ATP
Categories
UNII
Not Available
CAS number
Not Available
Weight
Average: 719.2755
Monoisotopic: 719.004334313
Chemical Formula
C15H25N5O20P4
InChI Key
RKNHJBVBFHDXGR-MRUDJCSFSA-N
InChI
InChI=1S/C15H25N5O20P4/c16-12-7-13(18-4-19(12)14-10(23)8(21)5(37-14)1-35-41(25,26)27)20(3-17-7)15-11(24)9(22)6(38-15)2-36-43(31,32)40-44(33,34)39-42(28,29)30/h3-6,8-11,14-16,21-24H,1-2H2,(H,31,32)(H,33,34)(H2,25,26,27)(H2,28,29,30)/t5-,6-,8-,9-,10-,11-,14?,15-/m1/s1
IUPAC Name
({[({[(2R,3S,4R,5R)-5-{1-[(3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-6-imino-6,9-dihydro-1H-purin-9-yl}-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
SMILES
O[C@@H]1[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C1N=CN(C1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O)C2=N

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UATP phosphoribosyltransferaseNot 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
KEGG Compound
C02739
PubChem Compound
16019963
PubChem Substance
46507757
ChemSpider
21864848
ChEBI
18263
HET
PRT

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 Solubility9.92 mg/mLALOGPS
logP-0.35ALOGPS
logP-5ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)1.1ChemAxon
pKa (Strongest Basic)0.6ChemAxon
Physiological Charge-5ChemAxon
Hydrogen Acceptor Count20ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area383.23 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity144.29 m3·mol-1ChemAxon
Polarizability57.34 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9694
Blood Brain Barrier+0.8629
Caco-2 permeable-0.6992
P-glycoprotein substrateNon-substrate0.5892
P-glycoprotein inhibitor INon-inhibitor0.8937
P-glycoprotein inhibitor IINon-inhibitor0.8825
Renal organic cation transporterNon-inhibitor0.9119
CYP450 2C9 substrateNon-substrate0.8213
CYP450 2D6 substrateNon-substrate0.8266
CYP450 3A4 substrateNon-substrate0.5196
CYP450 1A2 substrateNon-inhibitor0.8721
CYP450 2C9 inhibitorNon-inhibitor0.9093
CYP450 2D6 inhibitorNon-inhibitor0.9016
CYP450 2C19 inhibitorNon-inhibitor0.9033
CYP450 3A4 inhibitorNon-inhibitor0.9001
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9672
Ames testNon AMES toxic0.7643
CarcinogenicityNon-carcinogens0.8919
BiodegradationNot ready biodegradable0.936
Rat acute toxicity2.3619 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9522
hERG inhibition (predictor II)Non-inhibitor0.7641
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 MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0kaj-1739633400-e27af1b8e9489fa7241c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-1926510000-b4ec6881b642250063e7
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-001j-1943110000-bd22f77b44db9e4baba5
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-06dj-1647052900-24358b9ba8a747a31ede
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004j-9642210000-37824fa0d290e00eeb6b
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9420000000-314ee1336720e84cd8fc

Taxonomy

Description
This compound belongs to the class of organic compounds known as purine ribonucleoside triphosphates. These are purine ribobucleotides with a triphosphate group linked to the ribose moiety.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Purine nucleotides
Sub Class
Purine ribonucleotides
Direct Parent
Purine ribonucleoside triphosphates
Alternative Parents
Purine ribonucleoside monophosphates / Pentose phosphates / Glycosylamines / Monosaccharide phosphates / Purines and purine derivatives / Monoalkyl phosphates / Imidolactams / Pyrimidines and pyrimidine derivatives / N-substituted imidazoles / Heteroaromatic compounds
show 8 more
Substituents
Purine ribonucleoside triphosphate / Purine ribonucleoside monophosphate / Pentose phosphate / Pentose-5-phosphate / Glycosyl compound / N-glycosyl compound / Monosaccharide phosphate / Imidazopyrimidine / Purine / Monoalkyl phosphate
show 24 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
5-phosphoribosyl-ATP (CHEBI:18263)

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Magnesium ion binding
Specific Function
Catalyzes the condensation of ATP and 5-phosphoribose 1-diphosphate to form N'-(5'-phosphoribosyl)-ATP (PR-ATP). Has a crucial role in the pathway because the rate of histidine biosynthesis seems t...
Gene Name
hisG
Uniprot ID
P60757
Uniprot Name
ATP phosphoribosyltransferase
Molecular Weight
33366.32 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 June 04, 2019 05:21