Adenosine-5-Diphosphoribose

Identification

Name
Adenosine-5-Diphosphoribose
Accession Number
DB02059  (EXPT00544)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • ADPR
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 559.3157
Monoisotopic: 559.071673493
Chemical Formula
C15H23N5O14P2
InChI Key
SRNWOUGRCWSEMX-ZQSHOCFMSA-N
InChI
InChI=1S/C15H23N5O14P2/c16-12-7-13(18-3-17-12)20(4-19-7)14-10(23)8(21)5(32-14)1-30-35(26,27)34-36(28,29)31-2-6-9(22)11(24)15(25)33-6/h3-6,8-11,14-15,21-25H,1-2H2,(H,26,27)(H,28,29)(H2,16,17,18)/t5-,6-,8-,9-,10-,11-,14-,15+/m1/s1
IUPAC Name
{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[hydroxy({[(2R,3S,4R,5S)-3,4,5-trihydroxyoxolan-2-yl]methoxy})phosphoryl]oxy})phosphinic acid
SMILES

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UNAD-dependent protein deacylase sirtuin-5, mitochondrialNot AvailableHuman
Up-hydroxybenzoate hydroxylaseNot AvailablePseudomonas fluorescens
UADP-ribose pyrophosphataseNot AvailableShigella flexneri
UCDP-glucose 4,6-dehydrataseNot AvailableSalmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)
UElongation factor 2Not AvailableHuman
UGlyceraldehyde-3-phosphate dehydrogenaseNot AvailableHuman
ULactaldehyde reductaseNot AvailableEscherichia coli (strain K12)
UMutT/nudix family proteinNot AvailableMycobacterium tuberculosis
UADP compounds hydrolase NudENot AvailableEscherichia coli (strain K12)
UADP-ribose pyrophosphataseNot AvailableThermus thermophilus
UNAD-dependent protein deacetylase sirtuin-3, mitochondrialNot AvailableHuman
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
447048
PubChem Substance
46508870
ChemSpider
394252
HET
AR6
PDB Entries
2bfq / 2woe / 3pki / 3q71 / 3sig / 3v2b / 3vfq / 3x0k / 3x0l / 3x0m
show 30 more

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 Solubility3.61 mg/mLALOGPS
logP-1.8ALOGPS
logP-6.7ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area291.52 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity111.12 m3·mol-1ChemAxon
Polarizability46.29 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.941
Blood Brain Barrier+0.7803
Caco-2 permeable-0.753
P-glycoprotein substrateNon-substrate0.6857
P-glycoprotein inhibitor INon-inhibitor0.9107
P-glycoprotein inhibitor IINon-inhibitor0.9858
Renal organic cation transporterNon-inhibitor0.9597
CYP450 2C9 substrateNon-substrate0.8788
CYP450 2D6 substrateNon-substrate0.8378
CYP450 3A4 substrateNon-substrate0.572
CYP450 1A2 substrateNon-inhibitor0.8948
CYP450 2C9 inhibitorNon-inhibitor0.9263
CYP450 2D6 inhibitorNon-inhibitor0.8856
CYP450 2C19 inhibitorNon-inhibitor0.9138
CYP450 3A4 inhibitorNon-inhibitor0.8623
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9442
Ames testNon AMES toxic0.869
CarcinogenicityNon-carcinogens0.9273
BiodegradationNot ready biodegradable0.9606
Rat acute toxicity2.7259 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9633
hERG inhibition (predictor II)Non-inhibitor0.7767
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/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 purine nucleotide sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Purine nucleotides
Sub Class
Purine nucleotide sugars
Direct Parent
Purine nucleotide sugars
Alternative Parents
Purine ribonucleoside diphosphates / Purine ribonucleoside monophosphates / Pentose phosphates / Glycosylamines / 6-aminopurines / Organic pyrophosphates / Monosaccharide phosphates / Aminopyrimidines and derivatives / Monoalkyl phosphates / N-substituted imidazoles
show 12 more
Substituents
Purine nucleotide sugar / Purine ribonucleoside diphosphate / Purine ribonucleoside monophosphate / Pentose phosphate / Pentose-5-phosphate / Glycosyl compound / N-glycosyl compound / 6-aminopurine / Monosaccharide phosphate / Organic pyrophosphate
show 32 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
NAD-dependent lysine demalonylase, desuccinylase and deglutarylase that specifically removes malonyl, succinyl and glutaryl groups on target proteins (PubMed:21908771, PubMed:22076378, PubMed:24703...
Gene Name
SIRT5
Uniprot ID
Q9NXA8
Uniprot Name
NAD-dependent protein deacylase sirtuin-5, mitochondrial
Molecular Weight
33880.605 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]
  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:10592235]
Kind
Protein
Organism
Pseudomonas fluorescens
Pharmacological action
Unknown
General Function
Fad binding
Specific Function
Not Available
Gene Name
pobA
Uniprot ID
P00438
Uniprot Name
p-hydroxybenzoate hydroxylase
Molecular Weight
44321.205 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
Shigella flexneri
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Acts on ADP-mannose and ADP-glucose as well as ADP-ribose. Prevents glycogen biosynthesis. The reaction catalyzed by this enzyme is a limiting step of the gluconeogenic process (By similarity).
Gene Name
nudF
Uniprot ID
P83844
Uniprot Name
ADP-ribose pyrophosphatase
Molecular Weight
23666.61 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
Salmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)
Pharmacological action
Unknown
General Function
Cdp-glucose 4,6-dehydratase activity
Specific Function
Not Available
Gene Name
rfbG
Uniprot ID
P26397
Uniprot Name
CDP-glucose 4,6-dehydratase
Molecular Weight
41021.34 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
Human
Pharmacological action
Unknown
General Function
Translation elongation factor activity
Specific Function
Catalyzes the GTP-dependent ribosomal translocation step during translation elongation. During this step, the ribosome changes from the pre-translocational (PRE) to the post-translocational (POST) ...
Gene Name
EEF2
Uniprot ID
P13639
Uniprot Name
Elongation factor 2
Molecular Weight
95337.385 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]
  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:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Peptidyl-cysteine s-nitrosylase activity
Specific Function
Has both glyceraldehyde-3-phosphate dehydrogenase and nitrosylase activities, thereby playing a role in glycolysis and nuclear functions, respectively. Participates in nuclear events including tran...
Gene Name
GAPDH
Uniprot ID
P04406
Uniprot Name
Glyceraldehyde-3-phosphate dehydrogenase
Molecular Weight
36053.0 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]
  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:10592235]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Lactaldehyde reductase activity
Specific Function
Not Available
Gene Name
fucO
Uniprot ID
P0A9S1
Uniprot Name
Lactaldehyde reductase
Molecular Weight
40513.025 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
Mycobacterium tuberculosis
Pharmacological action
Unknown
General Function
Manganese ion binding
Specific Function
Not Available
Gene Name
Not Available
Uniprot ID
O33199
Uniprot Name
MutT/nudix family protein
Molecular Weight
22892.68 Da
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Magnesium ion binding
Specific Function
Active on adenosine(5')triphospho(5')adenosine (Ap3A), ADP-ribose, NADH, adenosine(5')diphospho(5')adenosine (Ap2A).
Gene Name
nudE
Uniprot ID
P45799
Uniprot Name
ADP compounds hydrolase NudE
Molecular Weight
21152.975 Da
Kind
Protein
Organism
Thermus thermophilus
Pharmacological action
Unknown
General Function
Nucleotide binding
Specific Function
Not Available
Gene Name
ndx4
Uniprot ID
Q84CU3
Uniprot Name
ADP-ribose pyrophosphatase
Molecular Weight
19263.785 Da
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
NAD-dependent protein deacetylase. Activates or deactivates mitochondrial target proteins by deacetylating key lysine residues. Known targets include ACSS1, IDH, GDH, SOD2, PDHA1, LCAD, SDHA and th...
Gene Name
SIRT3
Uniprot ID
Q9NTG7
Uniprot Name
NAD-dependent protein deacetylase sirtuin-3, mitochondrial
Molecular Weight
43572.71 Da
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:10592235]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 14:52