(10S,13S)-N-((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-yl)-2,12-dioxo-8-oxa-1,11-diazabicyclo[11.2.0]pentadecane-10-carboxamide

ID: ALA4866610

PubChem CID: 164624581

Max Phase: Preclinical

Molecular Formula: C22H35N3O6

Molecular Weight: 437.54

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)C[C@H](NC(=O)[C@@H]1COCCCCCC(=O)N2CC[C@H]2C(=O)N1)C(=O)[C@@]1(C)CO1

Standard InChI:  InChI=1S/C22H35N3O6/c1-14(2)11-15(19(27)22(3)13-31-22)23-20(28)16-12-30-10-6-4-5-7-18(26)25-9-8-17(25)21(29)24-16/h14-17H,4-13H2,1-3H3,(H,23,28)(H,24,29)/t15-,16-,17-,22+/m0/s1

Standard InChI Key:  SMYVVJLREYNLQH-ACTFIFLWSA-N

Molfile:  

 
     RDKit          2D

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   12.1097  -10.5982    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8281  -10.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4211   -9.4729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7027   -9.8799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   18.5354   -9.6589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9503   -8.9424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5809  -10.5348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6571  -11.3642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2591  -10.0651    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0072  -10.4129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6842   -9.9310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4340  -10.2751    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.6164   -9.1057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   17.1067   -9.7975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   17.9319  -10.9705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   19.2860  -10.0150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0138  -11.4034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2713  -11.7248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6650  -11.8863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8719  -12.6642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6526  -12.8760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2257  -12.2988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0063  -12.5064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5794  -11.9292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6940   -8.5064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5031   -8.5043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6892   -7.6946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2406   -9.4770    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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  2  8  1  0
  8  9  2  0
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 12 13  1  0
 12 14  2  0
 11 15  1  6
 13 16  1  0
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 17  6  1  0
  6 20  1  6
  1 21  1  0
 21 22  2  0
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 15 28  1  0
 19 29  1  0
 29 30  1  0
 29 31  1  0
  2 32  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4866610

   ---

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: 437.54

Molecular Weight (Monoisotopic): 437.2526

AlogP: 0.55

#Rotatable Bonds: 6

Polar Surface Area: 117.34

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.95

CX Basic pKa: ┄

CX LogP: 0.52

CX LogD: 0.52

Aromatic Rings: ┄

Heavy Atoms: 31

QED Weighted: 0.59

Np Likeness Score: 0.47

References

1. Lee MJ, Bhattarai D, Jang H, Baek A, Yeo IJ, Lee S, Miller Z, Lee S, Hong JT, Kim DE, Lee W, Kim KB..  (2021)  Macrocyclic Immunoproteasome Inhibitors as a Potential Therapy for Alzheimer's Disease.,  64  (15.0): [PMID:34309393] [10.1021/acs.jmedchem.1c00291]

Source

Source(1):

• Scientific Literature