(1r,4R)-N-((R)-1-((S)-1-((S)-3-cyclobutyl-1-((R)-2-methyloxiran-2-yl)-1-oxopropan-2-ylamino)-3-(4-methoxyphenyl)-1-oxopropan-2-ylamino)-1-oxopropan-2-yl)-4-hydroxycyclohexanecarboxamide

ID: ALA4550864

Chembl Id: CHEMBL4550864

PubChem CID: 117607978

Max Phase: Preclinical

Molecular Formula: C30H43N3O7

Molecular Weight: 557.69

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](CC2CCC2)C(=O)[C@@]2(C)CO2)cc1

Standard InChI:  InChI=1S/C30H43N3O7/c1-18(31-28(37)21-9-11-22(34)12-10-21)27(36)33-25(16-20-7-13-23(39-3)14-8-20)29(38)32-24(15-19-5-4-6-19)26(35)30(2)17-40-30/h7-8,13-14,18-19,21-22,24-25,34H,4-6,9-12,15-17H2,1-3H3,(H,31,37)(H,32,38)(H,33,36)/t18-,21-,22-,24+,25+,30-/m1/s1

Standard InChI Key:  VYPOZQXGEZGSAJ-MPEFJUCNSA-N

Alternative Forms

1. Parent:

   

   ALA4550864

   N-[(2R)-1-[[(2S)-1-[[(2S)-3-cyclobutyl-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: 557.69

Molecular Weight (Monoisotopic): 557.3101

AlogP: 1.81

#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: 11.94

CX Basic pKa: ┄

CX LogP: 2.26

CX LogD: 2.26

Aromatic Rings: 1

Heavy Atoms: 40

QED Weighted: 0.27

Np Likeness Score: 0.14

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