benzyl (2S)-1-((2S)-1-((3S)-1-(benzylamino)-2-hydroxy-5-methyl-1-oxohexan-3-ylamino)-4-methyl-1-oxopentan-2-ylamino)-4-methyl-1-oxopentan-2-ylcarbamate

ID: ALA4570264

PubChem CID: 155562443

Max Phase: Preclinical

Molecular Formula: C34H50N4O6

Molecular Weight: 610.80

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)C[C@H](NC(=O)OCc1ccccc1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(O)C(=O)NCc1ccccc1

Standard InChI:  InChI=1S/C34H50N4O6/c1-22(2)17-27(30(39)33(42)35-20-25-13-9-7-10-14-25)36-31(40)28(18-23(3)4)37-32(41)29(19-24(5)6)38-34(43)44-21-26-15-11-8-12-16-26/h7-16,22-24,27-30,39H,17-21H2,1-6H3,(H,35,42)(H,36,40)(H,37,41)(H,38,43)/t27-,28-,29-,30?/m0/s1

Standard InChI Key:  RGYZMHKJTLMCDY-UNVCSADESA-N

Molfile:  

 
     RDKit          2D

 44 45  0  0  0  0  0  0  0  0999 V2000
    2.9083  -18.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6228  -18.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3373  -18.6292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0517  -18.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7662  -18.6292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0517  -17.3918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4807  -18.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1952  -18.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3579  -17.4008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1952  -19.4543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9097  -18.2167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9980  -16.8784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7693  -17.1709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8657  -16.0639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6242  -18.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3386  -18.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6242  -19.4543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0531  -18.6292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3386  -17.3918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1150  -19.9740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9914  -20.8305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8522  -19.7003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7676  -18.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4820  -18.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7676  -17.3918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4820  -16.9793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0531  -16.9793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1965  -17.3918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4820  -16.1543    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1965  -15.7418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9110  -16.1543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9056  -16.9803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6193  -17.3927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3348  -16.9802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3320  -16.1510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6179  -15.7423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1944  -18.2138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4803  -18.6256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4799  -19.4515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1994  -19.8638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9105  -19.4497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4820  -19.4543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1965  -19.8668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7676  -19.8668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  5  7  1  0
  7  8  1  0
  7  9  1  1
  8 10  2  0
  8 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  1  0
 11 15  1  0
 15 16  1  0
 15 17  1  6
 16 18  1  0
 16 19  2  0
 17 20  1  0
 20 21  1  0
 20 22  1  0
 18 23  1  0
 23 24  1  6
 23 25  1  0
 25 26  1  0
 25 27  1  0
 26 28  2  0
 26 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  2  0
 36 31  1  0
  1 37  2  0
 37 38  1  0
 38 39  2  0
 39 40  1  0
 40 41  2  0
 41  1  1  0
 24 42  1  0
 42 43  1  0
 42 44  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4570264

   ---

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: 610.80

Molecular Weight (Monoisotopic): 610.3730

AlogP: 4.07

#Rotatable Bonds: 17

Polar Surface Area: 145.86

Molecular Species: NEUTRAL

HBA: 6

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.22

CX Basic pKa: ┄

CX LogP: 4.78

CX LogD: 4.78

Aromatic Rings: 2

Heavy Atoms: 44

QED Weighted: 0.18

Np Likeness Score: -0.14

References

1. Pacifico S, Ferretti V, Albanese V, Fantinati A, Gallerani E, Nicoli F, Gavioli R, Zamberlan F, Preti D, Marastoni M..  (2019)  Synthesis and Biological Activity of Peptide α-Ketoamide Derivatives as Proteasome Inhibitors.,  10  (7): [PMID:31312413] [10.1021/acsmedchemlett.9b00233]

Source

Source(1):

• Scientific Literature