NAV

2',3'-O-{4-[Hydroxy(oxido)-λ5-azanylidene]-2,6-dinitro-2,5-cyclohexadiene-1,1-diyl}adenosine 5'-(tetrahydrogen triphosphate)

Identification

Generic Name
2',3'-O-{4-[Hydroxy(oxido)-λ5-azanylidene]-2,6-dinitro-2,5-cyclohexadiene-1,1-diyl}adenosine 5'-(tetrahydrogen triphosphate)
DrugBank Accession Number
DB02524
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 718.27
Monoisotopic: 717.982281353
Chemical Formula
C16H17N8O19P3
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
UChemotaxis protein CheANot AvailableThermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
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 triphosphates. These are purine ribobucleotides with a triphosphate group linked to the ribose moiety.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Purine nucleotides
Sub Class
Purine ribonucleotides
Direct Parent
Purine ribonucleoside triphosphates
Alternative Parents
Purine ribonucleoside monophosphates / Pentose phosphates / 6-aminopurines / Monosaccharide phosphates / Aminopyrimidines and derivatives / Ketals / Monoalkyl phosphates / Imidolactams / N-substituted imidazoles / Tetrahydrofurans
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Substituents
6-aminopurine / Acetal / Alkyl phosphate / Allyl-type 1,3-dipolar organic compound / Amine / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Azole / C-nitro compound
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Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
XFMMHXLUHKBKQE-UHEGPQQHSA-N
InChI
InChI=1S/C16H17N8O19P3/c17-13-10-14(19-4-18-13)21(5-20-10)15-12-11(7(39-15)3-38-45(34,35)43-46(36,37)42-44(31,32)33)40-16(41-12)8(23(27)28)1-6(22(25)26)2-9(16)24(29)30/h1-2,4-5,7,11-12,15H,3H2,(H,25,26)(H,34,35)(H,36,37)(H2,17,18,19)(H2,31,32,33)/t7-,11-,12-,15-/m1/s1
IUPAC Name
[(3'aR,4'R,6'R,6'aR)-4'-(6-amino-9H-purin-9-yl)-6'-({[hydroxy({[hydroxy(phosphonooxy)phosphoryl]oxy})phosphoryl]oxy}methyl)-2,6-dinitro-3'a,4',6',6'a-tetrahydrospiro[cyclohexane-1,2'-furo[3,4-d][1,3]dioxole]-2,5-dien-4-ylidene]azinic acid
SMILES
[H]N([H])C1=C2N=CN([C@@H]3O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@]4([H])OC5(O[C@@]34[H])C(=CC(C=C5[N+]([O-])=O)=[N+](O)[O-])[N+]([O-])=O)C2=NC=N1

References

General References
Not Available
PubChem Compound
644358
PubChem Substance
46507848
ChemSpider
559362
ZINC
ZINC000096900390
PDBe Ligand
128
PDB Entries
1i5d / 2gvd / 2pmk / 3ar7 / 5a3s / 5ncq / 5svq / 5xw6 / 6yaa / 6yso

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 Solubility2.15 mg/mLALOGPS
logP0.5ALOGPS
logP-7.6Chemaxon
logS-2.5ALOGPS
pKa (Strongest Acidic)-0.5Chemaxon
pKa (Strongest Basic)4.93Chemaxon
Physiological Charge-4Chemaxon
Hydrogen Acceptor Count20Chemaxon
Hydrogen Donor Count6Chemaxon
Polar Surface Area389.71 Å2Chemaxon
Rotatable Bond Count10Chemaxon
Refractivity148.17 m3·mol-1Chemaxon
Polarizability53.85 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.7285
Blood Brain Barrier+0.7214
Caco-2 permeable-0.6199
P-glycoprotein substrateNon-substrate0.5391
P-glycoprotein inhibitor INon-inhibitor0.804
P-glycoprotein inhibitor IINon-inhibitor0.7682
Renal organic cation transporterNon-inhibitor0.9192
CYP450 2C9 substrateNon-substrate0.8395
CYP450 2D6 substrateNon-substrate0.8161
CYP450 3A4 substrateNon-substrate0.5276
CYP450 1A2 substrateNon-inhibitor0.6212
CYP450 2C9 inhibitorNon-inhibitor0.704
CYP450 2D6 inhibitorNon-inhibitor0.8538
CYP450 2C19 inhibitorNon-inhibitor0.6231
CYP450 3A4 inhibitorInhibitor0.5699
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5249
Ames testAMES toxic0.5607
CarcinogenicityNon-carcinogens0.824
BiodegradationNot ready biodegradable0.9813
Rat acute toxicity2.6379 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9484
hERG inhibition (predictor II)Non-inhibitor0.7651
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-203.29762
predicted
DeepCCS 1.0 (2019)
[M+H]+205.50966
predicted
DeepCCS 1.0 (2019)
[M+Na]+211.4222
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Chemotaxis protein CheA
Kind
Protein
Organism
Thermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
Pharmacological action
Unknown
General Function
Phosphorelay sensor kinase activity
Specific Function
Involved in the transmission of sensory signals from the chemoreceptors to the flagellar motors. CheA is autophosphorylated; it can transfer its phosphate group to either CheB or CheY (By similarity).
Gene Name
cheA
Uniprot ID
Q56310
Uniprot Name
Chemotaxis protein CheA
Molecular Weight
75555.3 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 July 02, 2020 13:18