Methyl (2S)-2-[[2-[(3R)-1-carbamimidoylpiperidin-3-yl]acetyl]amino]-3-[4-(2-phenylethynyl)phenyl]propanoate
Identification
- Generic Name
- Methyl (2S)-2-[[2-[(3R)-1-carbamimidoylpiperidin-3-yl]acetyl]amino]-3-[4-(2-phenylethynyl)phenyl]propanoate
- DrugBank Accession Number
- DB03453
- Background
This solid compound belongs to the 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. This substance targets the protein interleukin-2.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Methyl (2S)-2-[[2-[(3R)-1-carbamimidoylpiperidin-3-yl]acetyl]amino]-3-[4-(2-phenylethynyl)phenyl]propanoate (DB03453)
- Weight
- Average: 446.5414
Monoisotopic: 446.231790846 - Chemical Formula
- C26H30N4O3
- Synonyms
- Methyl N-{[(3R)-1-carbamimidoyl-3-piperidinyl]acetyl}-4-(phenylethynyl)-L-phenylalaninate
- External IDs
- Ro-264550
Pharmacology
- Indication
Not Available
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Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UInterleukin-2 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.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
- Phenylalanine and derivatives / Alpha amino acid esters / N-acyl-alpha amino acids and derivatives / Amphetamines and derivatives / Fatty acid esters / Piperidines / Methyl esters / Secondary carboxylic acid amides / Guanidines / Monocarboxylic acids and derivatives show 7 more
- Substituents
- Alpha-amino acid ester / Alpha-amino acid or derivatives / Amphetamine or derivatives / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxamide group / Carboximidamide / Carboxylic acid derivative show 21 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- 193744-04-6
- InChI Key
- MRNGXYMKYHNMLV-PKTZIBPZSA-N
- InChI
- InChI=1S/C26H30N4O3/c1-33-25(32)23(29-24(31)17-22-8-5-15-30(18-22)26(27)28)16-21-13-11-20(12-14-21)10-9-19-6-3-2-4-7-19/h2-4,6-7,11-14,22-23H,5,8,15-18H2,1H3,(H3,27,28)(H,29,31)/t22-,23+/m1/s1
- IUPAC Name
- methyl (2S)-2-{2-[(3R)-1-carbamimidoylpiperidin-3-yl]acetamido}-3-[4-(2-phenylethynyl)phenyl]propanoate
- SMILES
- [H]N=C(N([H])[H])N1CCC[C@H](CC(=O)N([H])[C@@H](CC2=CC=C(C=C2)C#CC2=CC=CC=C2)C(=O)OC)C1
References
- General References
- Not Available
- External Links
- PubChem Compound
- 5288250
- PubChem Substance
- 46508479
- ChemSpider
- 4450451
- BindingDB
- 50147974
- ChEMBL
- CHEMBL419362
- ZINC
- ZINC000013579788
- PDBe Ligand
- FRG
- PDB Entries
- 1m48
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 0.00858 mg/mL ALOGPS logP 2.74 ALOGPS logP 2.63 Chemaxon logS -4.7 ALOGPS pKa (Strongest Acidic) 12.4 Chemaxon pKa (Strongest Basic) 11.87 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 108.51 Å2 Chemaxon Rotatable Bond Count 9 Chemaxon Refractivity 133.33 m3·mol-1 Chemaxon Polarizability 50.57 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.6782 Blood Brain Barrier + 0.5546 Caco-2 permeable - 0.7035 P-glycoprotein substrate Substrate 0.8543 P-glycoprotein inhibitor I Inhibitor 0.6083 P-glycoprotein inhibitor II Non-inhibitor 0.7959 Renal organic cation transporter Inhibitor 0.521 CYP450 2C9 substrate Non-substrate 0.7914 CYP450 2D6 substrate Non-substrate 0.7693 CYP450 3A4 substrate Non-substrate 0.526 CYP450 1A2 substrate Non-inhibitor 0.8802 CYP450 2C9 inhibitor Non-inhibitor 0.6466 CYP450 2D6 inhibitor Non-inhibitor 0.8738 CYP450 2C19 inhibitor Non-inhibitor 0.7256 CYP450 3A4 inhibitor Non-inhibitor 0.6276 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9534 Ames test Non AMES toxic 0.7351 Carcinogenicity Non-carcinogens 0.9531 Biodegradation Not ready biodegradable 0.888 Rat acute toxicity 2.5963 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9112 hERG inhibition (predictor II) Inhibitor 0.6216
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Kinase activator activity
- Specific Function
- Produced by T-cells in response to antigenic or mitogenic stimulation, this protein is required for T-cell proliferation and other activities crucial to regulation of the immune response. Can stimu...
- Gene Name
- IL2
- Uniprot ID
- P60568
- Uniprot Name
- Interleukin-2
- Molecular Weight
- 17627.52 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- 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 June 13, 2005 13:24 / Updated at June 12, 2020 16:52