NAV

Gamma-Arsono-Beta, Gamma-Methyleneadenosine-5'-Diphosphate

Identification

Generic Name
Gamma-Arsono-Beta, Gamma-Methyleneadenosine-5'-Diphosphate
DrugBank Accession Number
DB02937
Background

Adenylic acid. Adenine nucleotide containing one phosphate group esterified to the sugar moiety in the 2'-, 3'-, or 5'-position. [PubChem]

Type
Small Molecule
Groups
Experimental
Structure
Similar Structures
Weight
Average: 549.156
Monoisotopic: 548.964315506
Chemical Formula
C11H18AsN5O12P2
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UNH(3)-dependent NAD(+) synthetaseNot AvailableEscherichia coli (strain K12)
UGlycerol kinaseNot 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
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
Pentose phosphates / Glycosylamines / 6-aminopurines / Monosaccharide phosphates / Aminopyrimidines and derivatives / Monoalkyl phosphates / Pentaorganoarsanes / Imidolactams / N-substituted imidazoles / Oxolanes
show 12 more
Substituents
1,2-diol / 6-aminopurine / Alcohol / Alkyl phosphate / Alkylarsine oxide / Amine / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Azole
show 37 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
KHQOAQLQNLUEQN-IOSLPCCCSA-N
InChI
InChI=1S/C11H18AsN5O12P2/c13-9-6-10(15-3-14-9)17(4-16-6)11-8(19)7(18)5(28-11)1-27-31(25,26)29-30(23,24)2-12(20,21)22/h3-5,7-8,11,18-19H,1-2H2,(H,23,24)(H,25,26)(H2,13,14,15)(H2,20,21,22)/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}({[(arsonomethyl)(hydroxy)phosphoryl]oxy})phosphinic acid
SMILES
[H][C@]1(COP(O)(=O)OP(O)(=O)C[As](O)(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
42626649
PubChem Substance
46505250
ChemSpider
26326201
PDBe Ligand
ATS
PDB Entries
1glj

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 Solubility3.62 mg/mLALOGPS
logP-1.5ALOGPS
logP-5.8Chemaxon
logS-2.2ALOGPS
pKa (Strongest Acidic)1.85Chemaxon
pKa (Strongest Basic)4.99Chemaxon
Physiological Charge-3Chemaxon
Hydrogen Acceptor Count14Chemaxon
Hydrogen Donor Count7Chemaxon
Polar Surface Area269.9 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity92.89 m3·mol-1Chemaxon
Polarizability41.31 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.9076
Blood Brain Barrier+0.8582
Caco-2 permeable-0.7094
P-glycoprotein substrateNon-substrate0.5876
P-glycoprotein inhibitor INon-inhibitor0.8823
P-glycoprotein inhibitor IINon-inhibitor0.9748
Renal organic cation transporterNon-inhibitor0.9602
CYP450 2C9 substrateNon-substrate0.8709
CYP450 2D6 substrateNon-substrate0.8286
CYP450 3A4 substrateNon-substrate0.5622
CYP450 1A2 substrateNon-inhibitor0.8427
CYP450 2C9 inhibitorNon-inhibitor0.9037
CYP450 2D6 inhibitorNon-inhibitor0.8652
CYP450 2C19 inhibitorNon-inhibitor0.8894
CYP450 3A4 inhibitorNon-inhibitor0.7651
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9573
Ames testNon AMES toxic0.7807
CarcinogenicityNon-carcinogens0.8761
BiodegradationNot ready biodegradable0.9593
Rat acute toxicity2.6011 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9661
hERG inhibition (predictor II)Non-inhibitor0.7869
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/MSsplash10-001i-0000090000-55b5b49c613c0051d995
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0000090000-3feb38ee623a758ca4ed
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-001j-0319140000-84873180350b5a9358a0
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-05di-2312590000-e20232745f9b95f20b5e
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-000f-0902200000-e4b3da7638beae3a6ae8
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0903580000-ef5adfc289daada408d4
Chromatographic Properties
Collision Cross Sections (CCS)
Not Available

Targets

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Details1. NH(3)-dependent NAD(+) synthetase
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Nad+ synthase activity
Specific Function
Catalyzes a key step in NAD biosynthesis, transforming deamido-NAD into NAD by a two-step reaction.
Gene Name
nadE
Uniprot ID
P18843
Uniprot Name
NH(3)-dependent NAD(+) synthetase
Molecular Weight
30636.56 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]
Details2. Glycerol kinase
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Key enzyme in the regulation of glycerol uptake and metabolism. Catalyzes the phosphorylation of glycerol to yield sn-glycerol 3-phosphate. It also catalyzes the phosphorylation of dihydroxyacetone...
Gene Name
glpK
Uniprot ID
P0A6F3
Uniprot Name
Glycerol kinase
Molecular Weight
56230.375 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