(S)-N-(6-(4-(6-methylpyridin-2-yl)piperazin-1-yl)-6-oxo-5-(2-phenylacetamido)hexyl)acrylamide

ID: ALA2203451

Chembl Id: CHEMBL2203451

PubChem CID: 71462877

Max Phase: Preclinical

Molecular Formula: C27H35N5O3

Molecular Weight: 477.61

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CC(=O)NCCCC[C@H](NC(=O)Cc1ccccc1)C(=O)N1CCN(c2cccc(C)n2)CC1

Standard InChI:  InChI=1S/C27H35N5O3/c1-3-25(33)28-15-8-7-13-23(30-26(34)20-22-11-5-4-6-12-22)27(35)32-18-16-31(17-19-32)24-14-9-10-21(2)29-24/h3-6,9-12,14,23H,1,7-8,13,15-20H2,2H3,(H,28,33)(H,30,34)/t23-/m0/s1

Standard InChI Key:  CLPJEHNKARSBTP-QHCPKHFHSA-N

Alternative Forms

1. Parent:

   

   ALA2203451

   N-[(5S)-6-[4-(6-methylpyridin-2-yl)piperazin-1-yl]-6-oxo-5-[(2-phenylacetyl)amino]hexyl]prop-2-enamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 477.61

Molecular Weight (Monoisotopic): 477.2740

AlogP: 2.24

#Rotatable Bonds: 11

Polar Surface Area: 94.64

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.63

CX Basic pKa: 7.19

CX LogP: 2.40

CX LogD: 2.20

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.38

Np Likeness Score: -1.15

References

1. Wityak J, Prime ME, Brookfield FA, Courtney SM, Erfan S, Johnsen S, Johnson PD, Li M, Marston RW, Reed L, Vaidya D, Schaertl S, Pedret-Dunn A, Beconi M, Macdonald D, Muñoz-Sanjuan I, Dominguez C..  (2012)  SAR Development of Lysine-Based Irreversible Inhibitors of Transglutaminase 2 for Huntington's Disease.,  3  (12): [PMID:24900424] [10.1021/ml300241m]

2. Song M, Hwang H, Im CY, Kim SY..  (2017)  Recent Progress in the Development of Transglutaminase 2 (TGase2) Inhibitors.,  60  (2): [PMID:28122456] [10.1021/acs.jmedchem.6b01036]

3. Wodtke R, Hauser C, Ruiz-Gómez G, Jäckel E, Bauer D, Lohse M, Wong A, Pufe J, Ludwig FA, Fischer S, Hauser S, Greif D, Pisabarro MT, Pietzsch J, Pietsch M, Löser R..  (2018)  Nε-Acryloyllysine Piperazides as Irreversible Inhibitors of Transglutaminase 2: Synthesis, Structure-Activity Relationships, and Pharmacokinetic Profiling.,  61  (10): [PMID:29664627] [10.1021/acs.jmedchem.8b00286]

Source

Source(1):

• Scientific Literature