N-((2S)-3-hydroxy-1-((2S)-1-hydroxy-1-((R)-2-methyloxiran-2-yl)-3-phenylpropan-2-ylamino)-1-oxopropan-2-yl)-6-oxo-1,6-dihydropyridine-2-carboxamide

ID: ALA4845896

PubChem CID: 164609059

Max Phase: Preclinical

Molecular Formula: C21H25N3O6

Molecular Weight: 415.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@]1(C(O)[C@H](Cc2ccccc2)NC(=O)[C@H](CO)NC(=O)c2cccc(=O)[nH]2)CO1

Standard InChI:  InChI=1S/C21H25N3O6/c1-21(12-30-21)18(27)15(10-13-6-3-2-4-7-13)23-20(29)16(11-25)24-19(28)14-8-5-9-17(26)22-14/h2-9,15-16,18,25,27H,10-12H2,1H3,(H,22,26)(H,23,29)(H,24,28)/t15-,16-,18?,21+/m0/s1

Standard InChI Key:  WPKBTFXXDYIAOB-QZOPPTLMSA-N

Molfile:  

 
     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
   19.5531   -3.2629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9677   -3.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3820   -3.2605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8302   -3.1521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8302   -3.9771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5398   -4.3835    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2534   -3.9771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2534   -3.1521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5398   -2.7335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1147   -4.3885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9689   -4.3885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9677   -5.2135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6816   -3.9791    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3971   -4.3906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1137   -3.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8251   -4.3926    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1149   -3.1562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3959   -5.2156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1114   -5.6311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5418   -3.9832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2573   -4.3947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6854   -4.3967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5430   -3.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0462   -2.5600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8144   -2.6980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3174   -2.1005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0500   -1.3635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2748   -1.2315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7751   -1.8302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2584   -5.2197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  1  3  1  0
  4  5  1  0
  4  9  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  5 10  2  0
  7 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 14 18  1  6
 18 19  1  0
 16 20  1  0
 20 21  1  0
 21  2  1  0
  2 22  1  6
 20 23  1  1
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
 21 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4845896

   ---

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: 415.45

Molecular Weight (Monoisotopic): 415.1743

AlogP: -0.66

#Rotatable Bonds: 9

Polar Surface Area: 144.05

Molecular Species: NEUTRAL

HBA: 6

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.57

CX Basic pKa: ┄

CX LogP: -0.96

CX LogD: -0.96

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.34

Np Likeness Score: 0.44

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