NAV

Alpha-Methylene Adenosine Monophosphate

Identification

Generic Name
Alpha-Methylene Adenosine Monophosphate
DrugBank Accession Number
DB02798
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 345.2484
Monoisotopic: 345.083819781
Chemical Formula
C11H16N5O6P
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
URibose-phosphate pyrophosphokinaseNot AvailableBacillus subtilis (strain 168)
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 / Pentoses / 6-aminopurines / Aminopyrimidines and derivatives / Phosphonic acid esters / N-substituted imidazoles / Imidolactams / Tetrahydrofurans / Organic phosphonic acids / Heteroaromatic compounds
show 9 more
Substituents
1,2-diol / 6-aminopurine / Alcohol / Amine / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Azole / Glycosyl compound / Heteroaromatic compound
show 26 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
PXSSQXBLDTZHLF-IOSLPCCCSA-N
InChI
InChI=1S/C11H16N5O6P/c1-23(19,20)21-2-5-7(17)8(18)11(22-5)16-4-15-6-9(12)13-3-14-10(6)16/h3-5,7-8,11,17-18H,2H2,1H3,(H,19,20)(H2,12,13,14)/t5-,7-,8-,11-/m1/s1
IUPAC Name
{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(methyl)phosphinic acid
SMILES
[H][C@]1(COP(C)(O)=O)O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])O

References

General References
Not Available
PubChem Compound
445093
PubChem Substance
46505912
ChemSpider
392835
ZINC
ZINC000003914599
PDBe Ligand
ABM
PDB Entries
1dku / 1ibs / 4y27 / 6ild

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 Solubility3.16 mg/mLALOGPS
logP-2.9ALOGPS
logP-4.8Chemaxon
logS-2ALOGPS
pKa (Strongest Acidic)1.41Chemaxon
pKa (Strongest Basic)3.94Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count9Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area165.84 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity76.59 m3·mol-1Chemaxon
Polarizability30.84 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.5641
Blood Brain Barrier+0.7904
Caco-2 permeable-0.711
P-glycoprotein substrateNon-substrate0.5729
P-glycoprotein inhibitor INon-inhibitor0.8878
P-glycoprotein inhibitor IINon-inhibitor0.9885
Renal organic cation transporterNon-inhibitor0.9458
CYP450 2C9 substrateNon-substrate0.8326
CYP450 2D6 substrateNon-substrate0.8325
CYP450 3A4 substrateSubstrate0.5159
CYP450 1A2 substrateNon-inhibitor0.8731
CYP450 2C9 inhibitorNon-inhibitor0.9223
CYP450 2D6 inhibitorNon-inhibitor0.901
CYP450 2C19 inhibitorNon-inhibitor0.9107
CYP450 3A4 inhibitorNon-inhibitor0.9391
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9614
Ames testNon AMES toxic0.8043
CarcinogenicityNon-carcinogens0.935
BiodegradationNot ready biodegradable0.9876
Rat acute toxicity2.1974 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9695
hERG inhibition (predictor II)Non-inhibitor0.8482
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/MSsplash10-0002-0029000000-c99cf48dd960d67b120e
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-002f-7009000000-d433884d0983a22595cf
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0940000000-a85b20a3d88f2c2bb46d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9001000000-2b52a3956fe7f19341c9
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-5900000000-7e28858945255797b669
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-06vi-9500000000-a6346e0c7696e21321d0
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-164.66042
predicted
DeepCCS 1.0 (2019)
[M+H]+167.05598
predicted
DeepCCS 1.0 (2019)
[M+Na]+172.9685
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Ribose-phosphate pyrophosphokinase
Kind
Protein
Organism
Bacillus subtilis (strain 168)
Pharmacological action
Unknown
General Function
Ribose phosphate diphosphokinase activity
Specific Function
Involved in the biosynthesis of ribose 1,5-bisphosphate. Catalyzes the transfer of pyrophosphoryl group from ATP to ribose-5-phosphate to yield phosphoribosyl diphosphate (PRPP) and AMP.
Gene Name
prs
Uniprot ID
P14193
Uniprot Name
Ribose-phosphate pyrophosphokinase
Molecular Weight
34867.88 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]

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