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(2S)-2-{3-[({[2-fluoro-4-(trifluoromethyl)phenyl]carbonyl}amino)methyl]-4-methoxybenzyl}butanoic acid

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Identification

Generic Name
(2S)-2-{3-[({[2-fluoro-4-(trifluoromethyl)phenyl]carbonyl}amino)methyl]-4-methoxybenzyl}butanoic acid
DrugBank Accession Number
DB07070
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 427.3894
Monoisotopic: 427.140670985
Chemical Formula
C21H21F4NO4
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UPeroxisome proliferator-activated receptor deltaNot AvailableHumans
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-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
Phenylpropanoic acids / 2-halobenzoic acids and derivatives / Trifluoromethylbenzenes / Anisoles / Benzoyl derivatives / Methoxybenzenes / Phenoxy compounds / Fluorobenzenes / Alkyl aryl ethers / Aryl fluorides
show 11 more
Substituents
2-halobenzoic acid or derivatives / 3-phenylpropanoic-acid / Alkyl aryl ether / Alkyl fluoride / Alkyl halide / Anisole / Aromatic homomonocyclic compound / Aryl fluoride / Aryl halide / Benzoyl
show 25 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
BDLLIPYDNFENMY-ZDUSSCGKSA-N
InChI
InChI=1S/C21H21F4NO4/c1-3-13(20(28)29)8-12-4-7-18(30-2)14(9-12)11-26-19(27)16-6-5-15(10-17(16)22)21(23,24)25/h4-7,9-10,13H,3,8,11H2,1-2H3,(H,26,27)(H,28,29)/t13-/m0/s1
IUPAC Name
(2S)-2-{[3-({[2-fluoro-4-(trifluoromethyl)phenyl]formamido}methyl)-4-methoxyphenyl]methyl}butanoic acid
SMILES
[H][C@](CC)(CC1=CC(CNC(=O)C2=C(F)C=C(C=C2)C(F)(F)F)=C(OC)C=C1)C(O)=O

References

General References
Not Available
PubChem Compound
11711595
PubChem Substance
99443541
ChemSpider
9886317
BindingDB
50176608
ChEMBL
CHEMBL202609
ZINC
ZINC000028569243
PDBe Ligand
401
PDB Entries
2znq

Clinical Trials

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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 Solubility0.00213 mg/mLALOGPS
logP3.93ALOGPS
logP4.7Chemaxon
logS-5.3ALOGPS
pKa (Strongest Acidic)4.08Chemaxon
pKa (Strongest Basic)-1.8Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area75.63 Å2Chemaxon
Rotatable Bond Count9Chemaxon
Refractivity102.38 m3·mol-1Chemaxon
Polarizability39.94 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9707
Blood Brain Barrier+0.8398
Caco-2 permeable-0.5352
P-glycoprotein substrateNon-substrate0.5106
P-glycoprotein inhibitor INon-inhibitor0.7862
P-glycoprotein inhibitor IINon-inhibitor0.6719
Renal organic cation transporterNon-inhibitor0.865
CYP450 2C9 substrateNon-substrate0.8533
CYP450 2D6 substrateNon-substrate0.7565
CYP450 3A4 substrateSubstrate0.5056
CYP450 1A2 substrateNon-inhibitor0.5356
CYP450 2C9 inhibitorNon-inhibitor0.6606
CYP450 2D6 inhibitorNon-inhibitor0.776
CYP450 2C19 inhibitorNon-inhibitor0.5338
CYP450 3A4 inhibitorNon-inhibitor0.659
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6381
Ames testNon AMES toxic0.677
CarcinogenicityNon-carcinogens0.8413
BiodegradationNot ready biodegradable0.9906
Rat acute toxicity2.5906 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9867
hERG inhibition (predictor II)Inhibitor0.5444
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/MSsplash10-004i-0119700000-45d265fe762a2e75177e
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03fr-0439300000-4cd485288ad9e138e886
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0036-0609100000-94da11bd51d30f2d67c1
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-1709200000-5d5f4edbe5a9eed601cf
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0096-0913100000-70c4f39f6db126b7dc58
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-05r4-4938200000-8a413fd906ac328961a7
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]-196.16228
predicted
DeepCCS 1.0 (2019)
[M+H]+198.52031
predicted
DeepCCS 1.0 (2019)
[M+Na]+205.62712
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Peroxisome proliferator-activated receptor delta
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Ligand-activated transcription factor key mediator of energy metabolism in adipose tissues (PubMed:35675826). Receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Has a preference for poly-unsaturated fatty acids, such as gamma-linoleic acid and eicosapentanoic acid. Once activated by a ligand, the receptor binds to promoter elements of target genes. Regulates the peroxisomal beta-oxidation pathway of fatty acids. Functions as transcription activator for the acyl-CoA oxidase gene. Decreases expression of NPC1L1 once activated by a ligand
Specific Function
DNA binding
Gene Name
PPARD
Uniprot ID
Q03181
Uniprot Name
Peroxisome proliferator-activated receptor delta
Molecular Weight
49902.99 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 21:18 / Updated at June 12, 2020 16:52