5-[Bis(2-bromoethyl)amino]-N-(2,3-dioxopropyl)-2,4-dinitrobenzamide

Identification

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Name
5-[Bis(2-bromoethyl)amino]-N-(2,3-dioxopropyl)-2,4-dinitrobenzamide
Accession Number
DB04138  (EXPT00668)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • 2,4-Dinitro,5-[bis(2-bromoethyl)amino]-N-(2',3'-dioxopropyl)benzamide
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 510.092
Monoisotopic: 507.922924116
Chemical Formula
C14H14Br2N4O7
InChI Key
LECLJMCDJUEAKI-UHFFFAOYSA-N
InChI
InChI=1S/C14H14Br2N4O7/c15-1-3-18(4-2-16)12-5-10(14(23)17-7-9(22)8-21)11(19(24)25)6-13(12)20(26)27/h5-6,8H,1-4,7H2,(H,17,23)
IUPAC Name
5-[bis(2-bromoethyl)amino]-N-(2,3-dioxopropyl)-2,4-dinitrobenzamide
SMILES
[H]N(CC(=O)C=O)C(=O)C1=CC(N(CCBr)CCBr)=C(C=C1[N+]([O-])=O)[N+]([O-])=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UOxygen-insensitive NAD(P)H nitroreductaseNot 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
Toxicity
Not Available
Affected organisms
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

References

General References
Not Available
External Links
PubChem Compound
5287756
PubChem Substance
46505867
ChemSpider
4450059
ZINC
ZINC000053684326
HET
BEL
PDB Entries
1oon

Clinical Trials

Clinical Trials
Not Available

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 Solubility0.00319 mg/mLALOGPS
logP2.58ALOGPS
logP2.63ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)11.38ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area152.76 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity102.25 m3·mol-1ChemAxon
Polarizability38.9 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9537
Blood Brain Barrier+0.6803
Caco-2 permeable-0.6188
P-glycoprotein substrateNon-substrate0.5284
P-glycoprotein inhibitor INon-inhibitor0.5769
P-glycoprotein inhibitor IINon-inhibitor0.631
Renal organic cation transporterNon-inhibitor0.8266
CYP450 2C9 substrateNon-substrate0.8499
CYP450 2D6 substrateNon-substrate0.827
CYP450 3A4 substrateNon-substrate0.5637
CYP450 1A2 substrateNon-inhibitor0.71
CYP450 2C9 inhibitorNon-inhibitor0.6453
CYP450 2D6 inhibitorNon-inhibitor0.8575
CYP450 2C19 inhibitorInhibitor0.5293
CYP450 3A4 inhibitorInhibitor0.5337
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6121
Ames testAMES toxic0.8321
CarcinogenicityNon-carcinogens0.5265
BiodegradationNot ready biodegradable0.9925
Rat acute toxicity2.6340 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6497
hERG inhibition (predictor II)Inhibitor0.5
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/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as dinitroanilines. These are organic compounds containing an aniline moiety, which is substituted at 2 positions by a nitro group.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Aniline and substituted anilines
Direct Parent
Dinitroanilines
Alternative Parents
Aminobenzamides / Benzamides / Nitrobenzenes / Benzoyl derivatives / Dialkylarylamines / Nitroaromatic compounds / Nitrogen mustard compounds / Alpha ketoaldehydes / Secondary carboxylic acid amides / Amino acids and derivatives
show 9 more
Substituents
Dinitroaniline / Aminobenzamide / Aminobenzoic acid or derivatives / Nitrobenzene / Benzoic acid or derivatives / Benzamide / Nitrogen mustard / Tertiary aliphatic/aromatic amine / Benzoyl / Nitroaromatic compound
show 30 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Nad(p)h nitroreductase activity
Specific Function
Reduction of a variety of nitroaromatic compounds using NADH (and to lesser extent NADPH) as source of reducing equivalents; two electrons are transferred. Capable of reducing nitrofurazone, quinon...
Gene Name
nfsB
Uniprot ID
P38489
Uniprot Name
Oxygen-insensitive NAD(P)H nitroreductase
Molecular Weight
23904.99 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. [PubMed:17139284]
  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. [PubMed:17016423]

Drug created on June 13, 2005 07:24 / Updated on February 06, 2020 11:54