(S)-2-[(R)-3-amino-4-(2-fluorophenyl)butyryl]-1,2,3,4-tetrahydroisoquinoline-3-carboxamide
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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
- Weight
- Average: 355.406
Monoisotopic: 355.169605168 - Chemical Formula
- C20H22FN3O2
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UDipeptidyl peptidase 4 Not Available Humans - 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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
- External Links
- PubChem Compound
- 5494385
- PubChem Substance
- 46507585
- ChemSpider
- 4591835
- BindingDB
- 11558
- ChEBI
- 39484
- ChEMBL
- CHEMBL381806
- ZINC
- ZINC000012504428
- PDBe Ligand
- 008
- PDB Entries
- 2buc
Clinical Trials
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
Property Value Source Water Solubility 0.052 mg/mL ALOGPS logP 1.35 ALOGPS logP 1.59 Chemaxon logS -3.8 ALOGPS pKa (Strongest Acidic) 15.65 Chemaxon pKa (Strongest Basic) 8.81 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 89.42 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 97.15 m3·mol-1 Chemaxon Polarizability 36.82 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9779 Blood Brain Barrier + 0.8987 Caco-2 permeable - 0.6345 P-glycoprotein substrate Substrate 0.6871 P-glycoprotein inhibitor I Inhibitor 0.8032 P-glycoprotein inhibitor II Non-inhibitor 0.672 Renal organic cation transporter Non-inhibitor 0.7004 CYP450 2C9 substrate Non-substrate 0.9107 CYP450 2D6 substrate Non-substrate 0.7298 CYP450 3A4 substrate Substrate 0.5192 CYP450 1A2 substrate Non-inhibitor 0.7179 CYP450 2C9 inhibitor Non-inhibitor 0.5492 CYP450 2D6 inhibitor Non-inhibitor 0.723 CYP450 2C19 inhibitor Inhibitor 0.5897 CYP450 3A4 inhibitor Non-inhibitor 0.7587 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.7074 Ames test Non AMES toxic 0.6968 Carcinogenicity Non-carcinogens 0.8527 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.4573 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9749 hERG inhibition (predictor II) Inhibitor 0.7561
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-0109000000-6899162de7591ea41e16 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0ue9-2869000000-8a9903b4909a98198b88 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4m-0936000000-ce71e1329cd1aac06c13 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-9010000000-be55197c638204d17086 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0ab9-1922000000-a0792d3b4fa643f365d1 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-9611000000-da43f411d6761ad4b780 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 177.30122 predictedDeepCCS 1.0 (2019) [M+H]+ 179.69678 predictedDeepCCS 1.0 (2019) [M+Na]+ 185.87613 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsDipeptidyl 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
- 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