(2S)-2-[[2-(azepan-1-yl)acetyl]amino]-N-[(1S)-1-benzyl-2-[[(1S)-1-benzyl-2-[(2R)-2-methyloxiran-2-yl]-2-oxo-ethyl]amino]-2-oxo-ethyl]-4-methyl-pentanamide

ID: ALA4465456

Chembl Id: CHEMBL4465456

PubChem CID: 155531358

Max Phase: Preclinical

Molecular Formula: C35H48N4O5

Molecular Weight: 604.79

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)C[C@H](NC(=O)CN1CCCCCC1)C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](Cc1ccccc1)C(=O)[C@@]1(C)CO1

Standard InChI:  InChI=1S/C35H48N4O5/c1-25(2)20-29(36-31(40)23-39-18-12-4-5-13-19-39)33(42)38-30(22-27-16-10-7-11-17-27)34(43)37-28(32(41)35(3)24-44-35)21-26-14-8-6-9-15-26/h6-11,14-17,25,28-30H,4-5,12-13,18-24H2,1-3H3,(H,36,40)(H,37,43)(H,38,42)/t28-,29-,30-,35+/m0/s1

Standard InChI Key:  BSASWESTQXYVIM-UAFVBSIISA-N

Alternative Forms

1. Parent:

   

   ALA4465456

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 604.79

Molecular Weight (Monoisotopic): 604.3625

AlogP: 3.21

#Rotatable Bonds: 15

Polar Surface Area: 120.14

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.10

CX Basic pKa: 7.61

CX LogP: 4.55

CX LogD: 4.13

Aromatic Rings: 2

Heavy Atoms: 44

QED Weighted: 0.27

Np Likeness Score: -0.19

References

1. Xi J, Zhuang R, Kong L, He R, Zhu H, Zhang J..  (2019)  Immunoproteasome-selective inhibitors: An overview of recent developments as potential drugs for hematologic malignancies and autoimmune diseases.,  182  [PMID:31521028] [10.1016/j.ejmech.2019.111646]

2. Johnson HWB, Lowe E, Anderl JL, Fan A, Muchamuel T, Bowers S, Moebius DC, Kirk C, McMinn DL..  (2018)  Required Immunoproteasome Subunit Inhibition Profile for Anti-Inflammatory Efficacy and Clinical Candidate KZR-616 ((2 S,3 R)- N-(( S)-3-(Cyclopent-1-en-1-yl)-1-(( R)-2-methyloxiran-2-yl)-1-oxopropan-2-yl)-3-hydroxy-3-(4-methoxyphenyl)-2-(( S)-2-(2-morpholinoacetamido)propanamido)propenamide).,  61  (24): [PMID:30380863] [10.1021/acs.jmedchem.8b01201]

Source

Source(1):

• Scientific Literature