N-[(1R)-2-[[(1S)-2-[[(1S)-1-(cyclopenten-1-ylmethyl)-2-[(2R)-2-methyloxiran-2-yl]-2-oxo-ethyl]amino]-1-[(4-methoxyphenyl)methyl]-2-oxo-ethyl]amino]-1-methyl-2-oxo-ethyl]-4-hydroxy-cyclohexanecarboxamide

ID: ALA4441524

Chembl Id: CHEMBL4441524

PubChem CID: 78425867

Max Phase: Preclinical

Molecular Formula: C31H43N3O7

Molecular Weight: 569.70

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C31H43N3O7/c1-19(32-29(38)22-10-12-23(35)13-11-22)28(37)34-26(17-21-8-14-24(40-3)15-9-21)30(39)33-25(16-20-6-4-5-7-20)27(36)31(2)18-41-31/h6,8-9,14-15,19,22-23,25-26,35H,4-5,7,10-13,16-18H2,1-3H3,(H,32,38)(H,33,39)(H,34,37)/t19-,22-,23-,25+,26+,31-/m1/s1

Standard InChI Key:  ONVNUBAXWAHVEF-WNVKXBHVSA-N

Alternative Forms

1. Parent:

   

   ALA4441524

   N-[(2R)-1-[[(2S)-1-[[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]amino]-3-(4-methoxyphenyl)-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]-4-hydroxycyclohexane-1-carboxamide

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: 569.70

Molecular Weight (Monoisotopic): 569.3101

AlogP: 2.12

#Rotatable Bonds: 13

Polar Surface Area: 146.36

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.93

CX Basic pKa: ┄

CX LogP: 2.30

CX LogD: 2.30

Aromatic Rings: 1

Heavy Atoms: 41

QED Weighted: 0.21

Np Likeness Score: 0.16

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