NAV

Adenosine 5'-methylenediphosphate

Identification

Generic Name
Adenosine 5'-methylenediphosphate
DrugBank Accession Number
DB03148
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 425.2283
Monoisotopic: 425.050150191
Chemical Formula
C11H17N5O9P2
Synonyms
  • Adenosine 5'-(hydrogen (phosphonomethyl)phosphonate)
  • Adenosine, 5'-(trihydrogen methylenebis(phosphonate))
  • Phosphomethylphosphonic acid adenosyl ester
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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
UDNANot AvailableHumans
URibose-phosphate pyrophosphokinaseNot AvailableBacillus subtilis (strain 168)
UMutT/nudix family proteinNot AvailableMycobacterium tuberculosis
UProtein UshANot 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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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
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 / Pentoses / Bisphosphonates / Aminopyrimidines and derivatives / Phosphonic acid esters / Imidolactams / N-substituted imidazoles / Organic phosphonic acids / Heteroaromatic compounds
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Substituents
1,2-diol / 6-aminopurine / Alcohol / Amine / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Azole / Bisphosphonate / Glycosyl compound
show 27 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
nucleoside diphosphate analogue (CHEBI:40730)
Affected organisms
Not Available

Chemical Identifiers

UNII
0T2A5439OE
CAS number
3768-14-7
InChI Key
OLCWZBFDIYXLAA-IOSLPCCCSA-N
InChI
InChI=1S/C11H17N5O9P2/c12-9-6-10(14-2-13-9)16(3-15-6)11-8(18)7(17)5(25-11)1-24-27(22,23)4-26(19,20)21/h2-3,5,7-8,11,17-18H,1,4H2,(H,22,23)(H2,12,13,14)(H2,19,20,21)/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}(hydroxy)phosphoryl)methyl]phosphonic acid
SMILES
NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)CP(O)(O)=O)[C@@H](O)[C@H]1O

References

General References
Not Available
PubChem Compound
92199
PubChem Substance
46508257
ChemSpider
83239
BindingDB
18136
ChEBI
40730
ChEMBL
CHEMBL583969
ZINC
ZINC000013527614
PDBe Ligand
AP2
PDB Entries
1av5 / 1dku / 1hpu / 1mr2 / 2vqd / 3dgr / 3fd5 / 3vth / 3zu0 / 4h2i …
show 11 more

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
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 Solubility3.36 mg/mLALOGPS
logP-1.9ALOGPS
logP-6Chemaxon
logS-2.1ALOGPS
pKa (Strongest Acidic)0.89Chemaxon
pKa (Strongest Basic)4.92Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count12Chemaxon
Hydrogen Donor Count6Chemaxon
Polar Surface Area223.37 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity87.3 m3·mol-1Chemaxon
Polarizability35.56 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.8991
Blood Brain Barrier+0.8723
Caco-2 permeable-0.725
P-glycoprotein substrateNon-substrate0.5208
P-glycoprotein inhibitor INon-inhibitor0.8699
P-glycoprotein inhibitor IINon-inhibitor0.9788
Renal organic cation transporterNon-inhibitor0.9623
CYP450 2C9 substrateNon-substrate0.8741
CYP450 2D6 substrateNon-substrate0.8309
CYP450 3A4 substrateNon-substrate0.5558
CYP450 1A2 substrateNon-inhibitor0.8474
CYP450 2C9 inhibitorNon-inhibitor0.9129
CYP450 2D6 inhibitorNon-inhibitor0.8768
CYP450 2C19 inhibitorNon-inhibitor0.8962
CYP450 3A4 inhibitorNon-inhibitor0.8252
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9691
Ames testNon AMES toxic0.7767
CarcinogenicityNon-carcinogens0.8649
BiodegradationNot ready biodegradable0.972
Rat acute toxicity2.5669 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9551
hERG inhibition (predictor II)Non-inhibitor0.7477
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/MSsplash10-004i-0001900000-08bdbc14992bec2884e4
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0000900000-e86eaea6c40fd20ef3b2
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0fc9-0539300000-08772382fcb16eb82600
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-05di-8401900000-da1b47649d6b97597023
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0910000000-92fbfe3bb9dbaef5084d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-003r-7903000000-4dd1a057fcdb48f07497
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]-170.9234
predicted
DeepCCS 1.0 (2019)
[M+H]+173.31897
predicted
DeepCCS 1.0 (2019)
[M+Na]+179.23149
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. DNA
Kind
Nucleotide
Organism
Humans
Pharmacological action
Unknown
DNA is the molecule of heredity, as it is responsible for the genetic propagation of most inherited traits. It is a polynucleic acid that carries genetic information on cell growth, division, and function. DNA consists of two long strands of nucleotides twisted into a double helix and held together by hydrogen bonds. The sequence of nucleotides determines hereditary characteristics. Each strand serves as the template for subsequent DNA replication and as a template for mRNA production, leading to protein synthesis via ribosomes.
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]
Details2. 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]
Details3. MutT/nudix family protein
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
Details4. Protein UshA
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Udp-sugar diphosphatase activity
Specific Function
Degradation of external UDP-glucose to uridine monophosphate and glucose-1-phosphate, which can then be used by the cell.
Gene Name
ushA
Uniprot ID
P07024
Uniprot Name
Protein UshA
Molecular Weight
60823.625 Da

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