5-[Bis-2(Chloro-Ethyl)-Amino]-2,4-Dintro-Benzamide

Identification

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Name
5-[Bis-2(Chloro-Ethyl)-Amino]-2,4-Dintro-Benzamide
Accession Number
DB03228  (EXPT02926)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 351.143
Monoisotopic: 350.018474928
Chemical Formula
C11H12Cl2N4O5
InChI Key
DQMALWRRERBILB-UHFFFAOYSA-N
InChI
InChI=1S/C11H12Cl2N4O5/c12-1-3-15(4-2-13)9-5-7(11(14)18)8(16(19)20)6-10(9)17(21)22/h5-6H,1-4H2,(H2,14,18)
IUPAC Name
5-[bis(2-chloroethyl)amino]-2,4-dinitrobenzamide
SMILES
NC(=O)C1=C(C=C(C(=C1)N(CCCl)CCCl)[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
126690
PubChem Substance
46506889
ChemSpider
112539
BindingDB
50004694
ChEMBL
CHEMBL281812
ZINC
ZINC000003930679
PDBe Ligand
SN2
PDB Entries
1oo6

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 Solubility0.00931 mg/mLALOGPS
logP1.83ALOGPS
logP2.14ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)11.29ChemAxon
pKa (Strongest Basic)-2.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area137.97 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity82.9 m3·mol-1ChemAxon
Polarizability30.58 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9636
Blood Brain Barrier+0.9404
Caco-2 permeable-0.5648
P-glycoprotein substrateNon-substrate0.6054
P-glycoprotein inhibitor INon-inhibitor0.8776
P-glycoprotein inhibitor IINon-inhibitor0.9024
Renal organic cation transporterNon-inhibitor0.7486
CYP450 2C9 substrateNon-substrate0.8722
CYP450 2D6 substrateNon-substrate0.8163
CYP450 3A4 substrateNon-substrate0.5238
CYP450 1A2 substrateNon-inhibitor0.613
CYP450 2C9 inhibitorNon-inhibitor0.6424
CYP450 2D6 inhibitorNon-inhibitor0.8444
CYP450 2C19 inhibitorInhibitor0.6567
CYP450 3A4 inhibitorNon-inhibitor0.5509
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6539
Ames testAMES toxic0.9018
CarcinogenicityNon-carcinogens0.5339
BiodegradationNot ready biodegradable0.9366
Rat acute toxicity2.5190 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.5868
hERG inhibition (predictor II)Non-inhibitor0.6849
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 GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
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 / Primary carboxylic acid amides / Amino acids and derivatives / Propargyl-type 1,3-dipolar organic compounds
show 8 more
Substituents
Dinitroaniline / Aminobenzamide / Aminobenzoic acid or derivatives / Benzamide / Benzoic acid or derivatives / Nitrobenzene / Nitroaromatic compound / Benzoyl / Nitrogen mustard / Tertiary aliphatic/aromatic amine
show 26 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]
  3. 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. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on February 06, 2020 11:41