NAV

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
3D
Similar Structures
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
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UInterleukin-2Not 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
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
PubChem Compound
5288250
PubChem Substance
46508479
ChemSpider
4450451
BindingDB
50147974
ChEMBL
CHEMBL419362
ZINC
ZINC000013579788
PDBe Ligand
FRG
PDB Entries
1m48

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 Solubility0.00858 mg/mLALOGPS
logP2.74ALOGPS
logP2.63Chemaxon
logS-4.7ALOGPS
pKa (Strongest Acidic)12.4Chemaxon
pKa (Strongest Basic)11.87Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area108.51 Å2Chemaxon
Rotatable Bond Count9Chemaxon
Refractivity133.33 m3·mol-1Chemaxon
Polarizability50.57 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.6782
Blood Brain Barrier+0.5546
Caco-2 permeable-0.7035
P-glycoprotein substrateSubstrate0.8543
P-glycoprotein inhibitor IInhibitor0.6083
P-glycoprotein inhibitor IINon-inhibitor0.7959
Renal organic cation transporterInhibitor0.521
CYP450 2C9 substrateNon-substrate0.7914
CYP450 2D6 substrateNon-substrate0.7693
CYP450 3A4 substrateNon-substrate0.526
CYP450 1A2 substrateNon-inhibitor0.8802
CYP450 2C9 inhibitorNon-inhibitor0.6466
CYP450 2D6 inhibitorNon-inhibitor0.8738
CYP450 2C19 inhibitorNon-inhibitor0.7256
CYP450 3A4 inhibitorNon-inhibitor0.6276
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9534
Ames testNon AMES toxic0.7351
CarcinogenicityNon-carcinogens0.9531
BiodegradationNot ready biodegradable0.888
Rat acute toxicity2.5963 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9112
hERG inhibition (predictor II)Inhibitor0.6216
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/MSsplash10-000j-0009600000-9aa5fba505d7bf1b6785
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-01ot-1032900000-daaeaa9d05b4af53f96e
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0219100000-8f313310b1418e56f9f7
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00dj-0129100000-3ccec20bafb42ccdfc0c
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0fe0-0922000000-a12ad3e468caac5d900d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0007-2629000000-fe5e4302359222cd1e55
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]-201.53859
predicted
DeepCCS 1.0 (2019)
[M+H]+203.93416
predicted
DeepCCS 1.0 (2019)
[M+Na]+211.13838
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Interleukin-2
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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. 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]
  3. 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