(5-CHLORO-2-{[(3-NITROBENZYL)AMINO]CARBONYL}PHENOXY)ACETIC ACID

Identification

Name
(5-CHLORO-2-{[(3-NITROBENZYL)AMINO]CARBONYL}PHENOXY)ACETIC ACID
Accession Number
DB07030
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: 364.737
Monoisotopic: 364.046213865
Chemical Formula
C16H13ClN2O6
InChI Key
VABIMMIJVWNHFI-UHFFFAOYSA-N
InChI
InChI=1S/C16H13ClN2O6/c17-11-4-5-13(14(7-11)25-9-15(20)21)16(22)18-8-10-2-1-3-12(6-10)19(23)24/h1-7H,8-9H2,(H,18,22)(H,20,21)
IUPAC Name
2-(5-chloro-2-{[(3-nitrophenyl)methyl]carbamoyl}phenoxy)acetic acid
SMILES
OC(=O)COC1=CC(Cl)=CC=C1C(=O)NCC1=CC(=CC=C1)[N+]([O-])=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UAldose reductaseNot AvailableHuman
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
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
16058630
PubChem Substance
99443501
ChemSpider
13438895
BindingDB
16239
ChEMBL
CHEMBL241577
HET
393
PDB Entries
2ikj / 2pdc / 2pdj / 2pdp / 2pdu / 2pzn / 3m64 / 3mc5

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 Solubility0.00755 mg/mLALOGPS
logP2.88ALOGPS
logP2.64ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)3ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area121.45 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity89.32 m3·mol-1ChemAxon
Polarizability34.28 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.5313
Blood Brain Barrier+0.7078
Caco-2 permeable-0.5699
P-glycoprotein substrateNon-substrate0.6473
P-glycoprotein inhibitor INon-inhibitor0.5592
P-glycoprotein inhibitor IINon-inhibitor0.5545
Renal organic cation transporterNon-inhibitor0.8982
CYP450 2C9 substrateNon-substrate0.7944
CYP450 2D6 substrateNon-substrate0.8388
CYP450 3A4 substrateNon-substrate0.5
CYP450 1A2 substrateInhibitor0.6254
CYP450 2C9 inhibitorInhibitor0.6212
CYP450 2D6 inhibitorNon-inhibitor0.7707
CYP450 2C19 inhibitorInhibitor0.6347
CYP450 3A4 inhibitorNon-inhibitor0.592
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8543
Ames testAMES toxic0.6897
CarcinogenicityNon-carcinogens0.5218
BiodegradationNot ready biodegradable0.9743
Rat acute toxicity2.4494 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9305
hERG inhibition (predictor II)Non-inhibitor0.6621
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 n-benzylbenzamides. These are compounds containing a benzamide moiety that is N-linked to a benzyl group.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzoic acids and derivatives
Direct Parent
N-benzylbenzamides
Alternative Parents
Chlorophenoxyacetates / 4-halobenzoic acids and derivatives / Nitrobenzenes / Phenoxy compounds / Phenol ethers / Benzoyl derivatives / Nitroaromatic compounds / Alkyl aryl ethers / Chlorobenzenes / Aryl chlorides
show 12 more
Substituents
N-benzylbenzamide / Chlorophenoxyacetate / Phenoxyacetate / 4-halobenzoic acid or derivatives / Halobenzoic acid or derivatives / Nitrobenzene / Nitroaromatic compound / Benzoyl / Phenoxy compound / Phenol ether
show 29 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Targets

Details
1. Aldose reductase
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Glyceraldehyde oxidoreductase activity
Specific Function
Catalyzes the NADPH-dependent reduction of a wide variety of carbonyl-containing compounds to their corresponding alcohols with a broad range of catalytic efficiencies.
Gene Name
AKR1B1
Uniprot ID
P15121
Uniprot Name
Aldose reductase
Molecular Weight
35853.125 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. [PubMed:10592235]

Drug created on September 15, 2010 15:18 / Updated on December 01, 2017 15:45