Benzyl ((2S)-1-(((2S)-4-(benzylamino)-3-hydroxy-1-(4-hydroxyphenyl)-4-oxobutan-2-yl)amino)-4-methyl-1-oxopentan-2-yl)carbamate

ID: ALA4585003

PubChem CID: 155562121

Max Phase: Preclinical

Molecular Formula: C31H37N3O6

Molecular Weight: 547.65

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)C[C@H](NC(=O)OCc1ccccc1)C(=O)N[C@@H](Cc1ccc(O)cc1)C(O)C(=O)NCc1ccccc1

Standard InChI:  InChI=1S/C31H37N3O6/c1-21(2)17-27(34-31(39)40-20-24-11-7-4-8-12-24)29(37)33-26(18-22-13-15-25(35)16-14-22)28(36)30(38)32-19-23-9-5-3-6-10-23/h3-16,21,26-28,35-36H,17-20H2,1-2H3,(H,32,38)(H,33,37)(H,34,39)/t26-,27-,28?/m0/s1

Standard InChI Key:  VUTSLBAEQXZJQU-ZLBDCPSSSA-N

Molfile:  

 
     RDKit          2D

 40 42  0  0  0  0  0  0  0  0999 V2000
   20.6611  -19.0529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3756  -18.6404    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.9467  -18.6404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6611  -19.8779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9467  -17.8155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2323  -17.4030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2353  -16.5770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5217  -16.1647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8063  -16.5771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8090  -17.4063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5231  -17.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0892  -19.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8045  -18.6404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1426  -19.8898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5189  -19.0529    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.8045  -17.8155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.2333  -18.6404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9477  -19.0529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6622  -18.6404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3766  -19.0529    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.6622  -17.8155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0910  -18.6404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8054  -19.0529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8038  -19.8790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5173  -20.2914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2327  -19.8788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2301  -19.0496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5159  -18.6409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8866  -20.2291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9654  -21.0503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5584  -19.7502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9477  -19.8779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.2333  -17.8155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8151  -17.2239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6186  -17.4349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2001  -16.8441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9788  -16.0434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1708  -15.8369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5928  -16.4293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5565  -15.4545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  0
  1  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  2 12  1  0
 12 13  1  0
 12 14  1  6
 13 15  1  0
 13 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 14 29  1  0
 29 30  1  0
 29 31  1  0
 18 32  1  0
 17 33  1  1
 33 34  1  0
 34 35  2  0
 35 36  1  0
 36 37  2  0
 37 38  1  0
 38 39  2  0
 39 34  1  0
 37 40  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4585003

   ---

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: 547.65

Molecular Weight (Monoisotopic): 547.2682

AlogP: 3.44

#Rotatable Bonds: 13

Polar Surface Area: 136.99

Molecular Species: NEUTRAL

HBA: 6

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.50

CX Basic pKa: ┄

CX LogP: 4.17

CX LogD: 4.16

Aromatic Rings: 3

Heavy Atoms: 40

QED Weighted: 0.22

Np Likeness Score: -0.04

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