NAV

1-(2-DEOXY-5-O-PHOSPHONO-BETA-D-ERYTHRO-PENTOFURANOSYL)-5-NITRO-1H-INDOLE

Identification

Generic Name
1-(2-DEOXY-5-O-PHOSPHONO-BETA-D-ERYTHRO-PENTOFURANOSYL)-5-NITRO-1H-INDOLE
DrugBank Accession Number
DB08245
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 358.2406
Monoisotopic: 358.056601978
Chemical Formula
C13H15N2O8P
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
UDNA polymeraseNot AvailableEnterobacteria phage RB69
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 n-alkylindoles. These are compounds containing an indole moiety that carries an alkyl chain at the 1-position.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Indoles and derivatives
Sub Class
N-alkylindoles
Direct Parent
N-alkylindoles
Alternative Parents
Indoles / Nitroaromatic compounds / Monoalkyl phosphates / Substituted pyrroles / Benzenoids / Tetrahydrofurans / Heteroaromatic compounds / Secondary alcohols / Azacyclic compounds / Propargyl-type 1,3-dipolar organic compounds
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Substituents
Alcohol / Alkyl phosphate / Allyl-type 1,3-dipolar organic compound / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / C-nitro compound / Heteroaromatic compound / Hydrocarbon derivative / Indole
show 20 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
FQCJFJRLZCIFHB-YNEHKIRRSA-N
InChI
InChI=1S/C13H15N2O8P/c16-11-6-13(23-12(11)7-22-24(19,20)21)14-4-3-8-5-9(15(17)18)1-2-10(8)14/h1-5,11-13,16H,6-7H2,(H2,19,20,21)/t11-,12+,13+/m0/s1
IUPAC Name
{[(2R,3S,5R)-3-hydroxy-5-(5-nitro-1H-indol-1-yl)oxolan-2-yl]methoxy}phosphonic acid
SMILES
[H][C@]1(O)C[C@@]([H])(O[C@]1([H])COP(O)(O)=O)N1C=CC2=CC(=CC=C12)[N+]([O-])=O

References

General References
Not Available
PubChem Compound
46937135
PubChem Substance
99444716
ChemSpider
25059115
ZINC
ZINC000053683036
PDBe Ligand
N5I
PDB Entries
2oyq

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 Solubility1.04 mg/mLALOGPS
logP0.41ALOGPS
logP1.23Chemaxon
logS-2.5ALOGPS
pKa (Strongest Acidic)1.23Chemaxon
pKa (Strongest Basic)-3.2Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area144.29 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity79.42 m3·mol-1Chemaxon
Polarizability31.85 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.8361
Blood Brain Barrier+0.9258
Caco-2 permeable-0.6273
P-glycoprotein substrateNon-substrate0.7129
P-glycoprotein inhibitor INon-inhibitor0.7602
P-glycoprotein inhibitor IINon-inhibitor0.7487
Renal organic cation transporterNon-inhibitor0.9093
CYP450 2C9 substrateNon-substrate0.872
CYP450 2D6 substrateNon-substrate0.818
CYP450 3A4 substrateSubstrate0.5684
CYP450 1A2 substrateNon-inhibitor0.6827
CYP450 2C9 inhibitorNon-inhibitor0.7554
CYP450 2D6 inhibitorNon-inhibitor0.8922
CYP450 2C19 inhibitorNon-inhibitor0.6823
CYP450 3A4 inhibitorNon-inhibitor0.7922
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7508
Ames testAMES toxic0.6342
CarcinogenicityNon-carcinogens0.7507
BiodegradationNot ready biodegradable0.9528
Rat acute toxicity2.5369 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8672
hERG inhibition (predictor II)Non-inhibitor0.7793
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 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-158.62752
predicted
DeepCCS 1.0 (2019)
[M+H]+161.02307
predicted
DeepCCS 1.0 (2019)
[M+Na]+166.93561
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. DNA polymerase
Kind
Protein
Organism
Enterobacteria phage RB69
Pharmacological action
Unknown
General Function
Nucleotide binding
Specific Function
Replicates the viral genomic DNA. This polymerase possesses two enzymatic activities: DNA synthesis (polymerase) and an exonucleolytic activity that degrades single-stranded DNA in the 3'- to 5'-di...
Gene Name
43
Uniprot ID
Q38087
Uniprot Name
DNA polymerase
Molecular Weight
104612.37 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at September 15, 2010 21:30 / Updated at June 12, 2020 16:52