(6S,9S)-1-Methyl-N-(4-methylbenzyl)-6-(2-(neopentylamino)-2-oxoethyl)-4,7-dioxo-4,5,6,7,8,9,10,12,13,14,15,16,17,18-tetradecahydro-1H-pyrazolo[4,3-i][1]oxa[4,7]diazacycloheptadecine-9-carboxamide

ID: ALA4542139

PubChem CID: 155551071

Max Phase: Preclinical

Molecular Formula: C32H48N6O5

Molecular Weight: 596.77

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1ccc(CNC(=O)[C@@H]2COCCCCCCCc3c(cnn3C)C(=O)N[C@@H](CC(=O)NCC(C)(C)C)C(=O)N2)cc1

Standard InChI:  InChI=1S/C32H48N6O5/c1-22-12-14-23(15-13-22)18-33-30(41)26-20-43-16-10-8-6-7-9-11-27-24(19-35-38(27)5)29(40)36-25(31(42)37-26)17-28(39)34-21-32(2,3)4/h12-15,19,25-26H,6-11,16-18,20-21H2,1-5H3,(H,33,41)(H,34,39)(H,36,40)(H,37,42)/t25-,26-/m0/s1

Standard InChI Key:  VYZYAEPKILNKBY-UIOOFZCWSA-N

Molfile:  

 
     RDKit          2D

 43 45  0  0  0  0  0  0  0  0999 V2000
   38.1451  -13.2545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8543  -13.6604    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.1420  -12.4373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.5605  -13.2492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2697  -13.6551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5574  -12.4320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2728  -14.4723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.9759  -13.2438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.6851  -13.6497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.3913  -13.2385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.1005  -13.6444    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.3882  -12.4213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   43.8067  -13.2332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.5159  -13.6391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.5166  -14.4546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.2250  -14.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.9322  -14.4492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.9264  -13.6278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.2175  -13.2256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1501  -14.8959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1514  -15.7131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8597  -16.1206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5668  -15.7109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2751  -16.1183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9822  -15.7086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6905  -16.1161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.3976  -15.3597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.6882  -14.4669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2635  -12.0207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2605  -11.2035    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.9728  -12.4266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.9666  -10.7923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9636   -9.9751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6697   -9.5638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2543   -9.5692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9586   -9.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.6419  -14.8541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4397  -14.4925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4389  -13.6657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6523  -13.4110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1670  -14.0804    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.6537  -14.7487    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.4020  -15.5261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 39  1  1  0
  1  2  1  0
  1  3  2  0
  2  4  1  0
  4  5  1  0
  4  6  1  1
  5  7  2  0
  5  8  1  0
  8  9  1  0
  9 10  1  6
 10 11  1  0
 10 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 38 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
  9 28  1  0
 28 27  1  0
  6 29  1  0
 29 30  1  0
 29 31  2  0
 30 32  1  0
 32 33  1  0
 33 34  1  0
 33 35  1  0
 33 36  1  0
 17 37  1  0
 38 39  2  0
 39 40  1  0
 40 41  2  0
 41 42  1  0
 42 38  1  0
 42 43  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4542139

   ---

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: 596.77

Molecular Weight (Monoisotopic): 596.3686

AlogP: 2.70

#Rotatable Bonds: 6

Polar Surface Area: 143.45

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 10.99

CX Basic pKa: 1.67

CX LogP: 2.66

CX LogD: 2.66

Aromatic Rings: 2

Heavy Atoms: 43

QED Weighted: 0.40

Np Likeness Score: -0.83

References

1. Yu J, Liu J, Li D, Xu L, Hong D, Chang S, Xu L, Li J, Liu T, Zhou Y..  (2019)  Exploration of novel macrocyclic dipeptide N-benzyl amides as proteasome inhibitors.,  164  [PMID:30611983] [10.1016/j.ejmech.2018.12.072]

Source

Source(1):

• Scientific Literature