AMPCPR

Identification

Generic Name
AMPCPR
DrugBank Accession Number
DB01975
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 557.3429
Monoisotopic: 557.092408935
Chemical Formula
C16H25N5O13P2
Synonyms
  • alpha-beta methylene ADP-ribose

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UADP-ribose pyrophosphataseNot AvailableShigella flexneri
UMutT/nudix family proteinNot AvailableMycobacterium tuberculosis
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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Purine nucleotides
Sub Class
Purine ribonucleotides
Direct Parent
Purine ribonucleoside monophosphates
Alternative Parents
Glycosylamines / 6-aminopurines / Bisphosphonates / Aminopyrimidines and derivatives / Phosphonic acid esters / Imidolactams / Monosaccharides / N-substituted imidazoles / Tetrahydrofurans / Heteroaromatic compounds
show 11 more
Substituents
6-aminopurine / Alcohol / Amine / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Azole / Bisphosphonate / Glycosyl compound / Hemiacetal
show 27 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
ZPZRETFSCSWNDT-DBXCYWGHSA-N
InChI
InChI=1S/C16H25N5O13P2/c17-13-8-14(19-3-18-13)21(4-20-8)15-11(24)9(22)6(33-15)1-31-35(27,28)5-36(29,30)32-2-7-10(23)12(25)16(26)34-7/h3-4,6-7,9-12,15-16,22-26H,1-2,5H2,(H,27,28)(H,29,30)(H2,17,18,19)/t6-,7-,9-,10-,11-,12-,15-,16+/m1/s1
IUPAC Name
[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)methyl]({[(2R,3S,4R,5S)-3,4,5-trihydroxyoxolan-2-yl]methoxy})phosphinic acid
SMILES
[H][C@]1(O)O[C@]([H])(COP(O)(=O)CP(O)(=O)OC[C@@]2([H])O[C@@]([H])(N3C=NC4=C(N)N=CN=C34)[C@]([H])(O)[C@]2([H])O)[C@@]([H])(O)[C@@]1([H])O

References

General References
Not Available
PubChem Compound
446724
PubChem Substance
46508105
ChemSpider
394008
ZINC
ZINC000015636817
PDBe Ligand
ADV
PDB Entries
1khz / 1mqw / 3bm4 / 4zbp

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility4.24 mg/mLALOGPS
logP-2ALOGPS
logP-7.6Chemaxon
logS-2.1ALOGPS
pKa (Strongest Acidic)0.6Chemaxon
pKa (Strongest Basic)4.92Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count15Chemaxon
Hydrogen Donor Count8Chemaxon
Polar Surface Area282.29 Å2Chemaxon
Rotatable Bond Count9Chemaxon
Refractivity113.48 m3·mol-1Chemaxon
Polarizability47.57 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.9376
Blood Brain Barrier+0.7573
Caco-2 permeable-0.7349
P-glycoprotein substrateNon-substrate0.5893
P-glycoprotein inhibitor INon-inhibitor0.878
P-glycoprotein inhibitor IINon-inhibitor0.9832
Renal organic cation transporterNon-inhibitor0.9693
CYP450 2C9 substrateNon-substrate0.9028
CYP450 2D6 substrateNon-substrate0.8338
CYP450 3A4 substrateNon-substrate0.5556
CYP450 1A2 substrateNon-inhibitor0.8584
CYP450 2C9 inhibitorNon-inhibitor0.9078
CYP450 2D6 inhibitorNon-inhibitor0.8722
CYP450 2C19 inhibitorNon-inhibitor0.887
CYP450 3A4 inhibitorNon-inhibitor0.7461
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9468
Ames testNon AMES toxic0.782
CarcinogenicityNon-carcinogens0.8895
BiodegradationNot ready biodegradable0.9564
Rat acute toxicity2.6179 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9562
hERG inhibition (predictor II)Non-inhibitor0.7535
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/MSsplash10-0a4i-0000190000-762ec7616c4d26672643
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0000090000-8ae7535603d52d90adb7
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4r-1230590000-627e69bb809f02f3be2c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a6r-0212930000-3aab2d2c583136fc7e75
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-052r-1926310000-e0cf1bebe582359dc08a
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0536-4965640000-4aed9a3e83034c8fd702
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-187.29773
predicted
DeepCCS 1.0 (2019)
[M+H]+189.55974
predicted
DeepCCS 1.0 (2019)
[M+Na]+195.47221
predicted
DeepCCS 1.0 (2019)

Targets

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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. [Article]
  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. [Article]
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

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52