(1r,4R)-4-hydroxy-N-((R)-1-((S)-3-(4-methoxyphenyl)-1-((S)-1-((R)-2-methyloxiran-2-yl)-1-oxo-3-phenylpropan-2-ylamino)-1-oxopropan-2-ylamino)-1-oxopropan-2-yl)cyclohexanecarboxamide

ID: ALA4454809

Chembl Id: CHEMBL4454809

PubChem CID: 117607839

Max Phase: Preclinical

Molecular Formula: C32H41N3O7

Molecular Weight: 579.69

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](Cc2ccccc2)C(=O)[C@@]2(C)CO2)cc1

Standard InChI:  InChI=1S/C32H41N3O7/c1-20(33-30(39)23-11-13-24(36)14-12-23)29(38)35-27(18-22-9-15-25(41-3)16-10-22)31(40)34-26(28(37)32(2)19-42-32)17-21-7-5-4-6-8-21/h4-10,15-16,20,23-24,26-27,36H,11-14,17-19H2,1-3H3,(H,33,39)(H,34,40)(H,35,38)/t20-,23-,24-,26+,27+,32-/m1/s1

Standard InChI Key:  DMAYUUDCUFRNPK-JTRPPKJJSA-N

Alternative Forms

1. Parent:

   

   ALA4454809

   4-hydroxy-N-[(2R)-1-[[(2S)-3-(4-methoxyphenyl)-1-[[(2S)-1-[(2R)-2-methyloxiran-2-yl]-1-oxo-3-phenylpropan-2-yl]amino]-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]cyclohexane-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: 579.69

Molecular Weight (Monoisotopic): 579.2945

AlogP: 1.86

#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: 11.92

CX Basic pKa: ┄

CX LogP: 2.68

CX LogD: 2.68

Aromatic Rings: 2

Heavy Atoms: 42

QED Weighted: 0.27

Np Likeness Score: 0.03

References

1. 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