NAV

4'-[(1R)-1-amino-2-(2,5-difluorophenyl)ethyl]biphenyl-3-carboxamide

Identification

Generic Name
4'-[(1R)-1-amino-2-(2,5-difluorophenyl)ethyl]biphenyl-3-carboxamide
DrugBank Accession Number
DB07181
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 352.3772
Monoisotopic: 352.138719618
Chemical Formula
C21H18F2N2O
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UDipeptidyl peptidase 4Not 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 stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Stilbenes
Sub Class
Not Available
Direct Parent
Stilbenes
Alternative Parents
Biphenyls and derivatives / Amphetamines and derivatives / Benzamides / Benzoyl derivatives / Fluorobenzenes / Aralkylamines / Aryl fluorides / Primary carboxylic acid amides / Amino acids and derivatives / Organopnictogen compounds
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Substituents
Amine / Amino acid or derivatives / Amphetamine or derivatives / Aralkylamine / Aromatic homomonocyclic compound / Aryl fluoride / Aryl halide / Benzamide / Benzenoid / Benzoic acid or derivatives
show 20 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
JYKFWUXBFJJDTP-HXUWFJFHSA-N
InChI
InChI=1S/C21H18F2N2O/c22-18-8-9-19(23)17(11-18)12-20(24)14-6-4-13(5-7-14)15-2-1-3-16(10-15)21(25)26/h1-11,20H,12,24H2,(H2,25,26)/t20-/m1/s1
IUPAC Name
4'-[(1R)-1-amino-2-(2,5-difluorophenyl)ethyl]-[1,1'-biphenyl]-3-carboxamide
SMILES
[H][C@@](N)(CC1=CC(F)=CC=C1F)C1=CC=C(C=C1)C1=CC=CC(=C1)C(N)=O

References

General References
Not Available
PubChem Compound
24832041
PubChem Substance
99443652
ChemSpider
23329644
BindingDB
50244011
ChEMBL
CHEMBL452289
ZINC
ZINC000024981641
PDBe Ligand
605
PDB Entries
3d4l

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 Solubility0.00117 mg/mLALOGPS
logP3.42ALOGPS
logP3.96Chemaxon
logS-5.5ALOGPS
pKa (Strongest Acidic)14.64Chemaxon
pKa (Strongest Basic)9.3Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area69.11 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity98.22 m3·mol-1Chemaxon
Polarizability35.67 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9945
Blood Brain Barrier+0.9956
Caco-2 permeable+0.6644
P-glycoprotein substrateNon-substrate0.6989
P-glycoprotein inhibitor INon-inhibitor0.6226
P-glycoprotein inhibitor IINon-inhibitor0.9635
Renal organic cation transporterNon-inhibitor0.8429
CYP450 2C9 substrateNon-substrate0.8519
CYP450 2D6 substrateNon-substrate0.8017
CYP450 3A4 substrateNon-substrate0.6562
CYP450 1A2 substrateInhibitor0.8158
CYP450 2C9 inhibitorInhibitor0.6471
CYP450 2D6 inhibitorNon-inhibitor0.7839
CYP450 2C19 inhibitorNon-inhibitor0.5067
CYP450 3A4 inhibitorNon-inhibitor0.7988
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8014
Ames testNon AMES toxic0.6644
CarcinogenicityNon-carcinogens0.5659
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.7032 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9964
hERG inhibition (predictor II)Non-inhibitor0.6357
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-MSsplash10-00c0-2792000000-5d65a73d5c1d1f58bbae
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0209000000-b2562d20994cd3b3f713
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001l-3039000000-d3a4c11f843f08bcc7e8
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014r-0019000000-2a95856f2fedd1e45af3
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9020000000-d5e532cb7bdb04159090
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-014l-0769000000-d758e1f589e2392f3ded
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9210000000-09e3e2e9c161c41d916e
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]-178.02728
predicted
DeepCCS 1.0 (2019)
[M+H]+180.38528
predicted
DeepCCS 1.0 (2019)
[M+Na]+187.30159
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Dipeptidyl peptidase 4
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Virus receptor activity
Specific Function
Cell surface glycoprotein receptor involved in the costimulatory signal essential for T-cell receptor (TCR)-mediated T-cell activation. Acts as a positive regulator of T-cell coactivation, by bindi...
Gene Name
DPP4
Uniprot ID
P27487
Uniprot Name
Dipeptidyl peptidase 4
Molecular Weight
88277.935 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 21:19 / Updated at June 12, 2020 16:52