(2S)-N-[(1S)-1-(cyclopenten-1-ylmethyl)-2-[(2R)-2-methyloxiran-2-yl]-2-oxo-ethyl]-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholinoacetyl)amino]propanoyl]amino]propanamide

ID: ALA4443505

Chembl Id: CHEMBL4443505

PubChem CID: 117607901

Max Phase: Preclinical

Molecular Formula: C30H42N4O7

Molecular Weight: 570.69

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(C[C@H](NC(=O)[C@H](C)NC(=O)CN2CCOCC2)C(=O)N[C@@H](CC2=CCCC2)C(=O)[C@@]2(C)CO2)cc1

Standard InChI:  InChI=1S/C30H42N4O7/c1-20(31-26(35)18-34-12-14-40-15-13-34)28(37)33-25(17-22-8-10-23(39-3)11-9-22)29(38)32-24(16-21-6-4-5-7-21)27(36)30(2)19-41-30/h6,8-11,20,24-25H,4-5,7,12-19H2,1-3H3,(H,31,35)(H,32,38)(H,33,37)/t20-,24-,25-,30+/m0/s1

Standard InChI Key:  CLZRGXQPCQFFTL-NHPFZIKMSA-N

Alternative Forms

1. Parent:

   

   ALA4443505

   (2S)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide

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: 570.69

Molecular Weight (Monoisotopic): 570.3053

AlogP: 0.90

#Rotatable Bonds: 14

Polar Surface Area: 138.60

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.83

CX Basic pKa: 5.04

CX LogP: 1.24

CX LogD: 1.24

Aromatic Rings: 1

Heavy Atoms: 41

QED Weighted: 0.22

Np Likeness Score: -0.34

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