NAV

(S)-2-[(R)-3-amino-4-(2-fluorophenyl)butyryl]-1,2,3,4-tetrahydroisoquinoline-3-carboxamide

Identification

Generic Name
(S)-2-[(R)-3-amino-4-(2-fluorophenyl)butyryl]-1,2,3,4-tetrahydroisoquinoline-3-carboxamide
DrugBank Accession Number
DB04578
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 355.406
Monoisotopic: 355.169605168
Chemical Formula
C20H22FN3O2
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 hybrid peptides. These are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Peptidomimetics
Sub Class
Hybrid peptides
Direct Parent
Hybrid peptides
Alternative Parents
Alpha amino acid amides / Beta amino acids and derivatives / Tetrahydroisoquinolines / Amphetamines and derivatives / Aralkylamines / Fluorobenzenes / Aryl fluorides / Tertiary carboxylic acid amides / Primary carboxylic acid amides / Azacyclic compounds
show 6 more
Substituents
Alpha-amino acid amide / Alpha-amino acid or derivatives / Amine / Amino acid or derivatives / Amphetamine or derivatives / Aralkylamine / Aromatic heteropolycyclic compound / Aryl fluoride / Aryl halide / Azacycle
show 24 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
isoquinolines (CHEBI:39484)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
OEVYDSSAPNIURZ-AEFFLSMTSA-N
InChI
InChI=1S/C20H22FN3O2/c21-17-8-4-3-6-14(17)9-16(22)11-19(25)24-12-15-7-2-1-5-13(15)10-18(24)20(23)26/h1-8,16,18H,9-12,22H2,(H2,23,26)/t16-,18+/m1/s1
IUPAC Name
(3S)-2-[(3R)-3-amino-4-(2-fluorophenyl)butanoyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxamide
SMILES
[H][C@](N)(CC(=O)N1CC2=CC=CC=C2C[C@@]1([H])C(N)=O)CC1=CC=CC=C1F

References

General References
Not Available
PubChem Compound
5494385
PubChem Substance
46507585
ChemSpider
4591835
BindingDB
11558
ChEBI
39484
ChEMBL
CHEMBL381806
ZINC
ZINC000012504428
PDBe Ligand
008
PDB Entries
2buc

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 Solubility0.052 mg/mLALOGPS
logP1.35ALOGPS
logP1.59Chemaxon
logS-3.8ALOGPS
pKa (Strongest Acidic)15.65Chemaxon
pKa (Strongest Basic)8.81Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area89.42 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity97.15 m3·mol-1Chemaxon
Polarizability36.82 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9779
Blood Brain Barrier+0.8987
Caco-2 permeable-0.6345
P-glycoprotein substrateSubstrate0.6871
P-glycoprotein inhibitor IInhibitor0.8032
P-glycoprotein inhibitor IINon-inhibitor0.672
Renal organic cation transporterNon-inhibitor0.7004
CYP450 2C9 substrateNon-substrate0.9107
CYP450 2D6 substrateNon-substrate0.7298
CYP450 3A4 substrateSubstrate0.5192
CYP450 1A2 substrateNon-inhibitor0.7179
CYP450 2C9 inhibitorNon-inhibitor0.5492
CYP450 2D6 inhibitorNon-inhibitor0.723
CYP450 2C19 inhibitorInhibitor0.5897
CYP450 3A4 inhibitorNon-inhibitor0.7587
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7074
Ames testNon AMES toxic0.6968
CarcinogenicityNon-carcinogens0.8527
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.4573 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9749
hERG inhibition (predictor II)Inhibitor0.7561
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/MSsplash10-0a4i-0109000000-6899162de7591ea41e16
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0ue9-2869000000-8a9903b4909a98198b88
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4m-0936000000-ce71e1329cd1aac06c13
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9010000000-be55197c638204d17086
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ab9-1922000000-a0792d3b4fa643f365d1
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9611000000-da43f411d6761ad4b780
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]-177.30122
predicted
DeepCCS 1.0 (2019)
[M+H]+179.69678
predicted
DeepCCS 1.0 (2019)
[M+Na]+185.87613
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 11, 2007 17:48 / Updated at June 12, 2020 16:52