((R)-1-((S)-2-hexanamido-3-phenylpropanamido)-3-methylbutyl)boronic acid

ID: ALA4246480

PubChem CID: 145985780

Max Phase: Preclinical

Molecular Formula: C20H33BN2O4

Molecular Weight: 376.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCC(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CC(C)C)B(O)O

Standard InChI:  InChI=1S/C20H33BN2O4/c1-4-5-7-12-19(24)22-17(14-16-10-8-6-9-11-16)20(25)23-18(21(26)27)13-15(2)3/h6,8-11,15,17-18,26-27H,4-5,7,12-14H2,1-3H3,(H,22,24)(H,23,25)/t17-,18-/m0/s1

Standard InChI Key:  UESZADMGJTUSQM-ROUUACIJSA-N

Molfile:  

     RDKit          2D

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   33.0232  -20.6381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7365  -21.0440    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.0201  -19.8168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.4468  -20.6328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1602  -21.0387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8664  -20.6274    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.1633  -21.8600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.5797  -21.0334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2900  -20.6221    0.0000 B   0  0  0  0  0  0  0  0  0  0  0  0
   36.5828  -21.8547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2962  -22.2647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2993  -23.0860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0065  -21.8493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0034  -21.0280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.2869  -19.8008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.3129  -21.0494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5995  -20.6434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4437  -19.8115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1540  -19.3961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8597  -19.8100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5695  -19.3953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5669  -18.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8485  -18.1674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1458  -18.5803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5964  -19.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8831  -19.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8800  -18.5908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  6
 10 11  1  0
 11 12  1  0
 11 13  1  0
  9 14  1  0
  9 15  1  0
  1 16  1  0
 16 17  1  0
  4 18  1  1
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 17 25  1  0
 25 26  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4246480

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 376.31

Molecular Weight (Monoisotopic): 376.2533

AlogP: ┄

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Molecular Species: ┄

HBA: ┄

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#RO5 Violations: ┄

HBA (Lipinski): ┄

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: ┄

CX LogD: ┄

Aromatic Rings: ┄

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QED Weighted: ┄

Np Likeness Score: ┄

References

1. Lei M, Feng H, Bai E, Zhou H, Wang J, Shi J, Wang X, Hu S, Liu Z, Zhu Y..  (2018)  Design, synthesis, in vitro and in vivo evaluation, and structure-activity relationship (SAR) discussion of novel dipeptidyl boronic acid proteasome inhibitors as orally available anti-cancer agents for the treatment of multiple myeloma and mechanism studies.,  26  (14): [PMID:29934218] [10.1016/j.bmc.2018.06.020]

Source

Source(1):

• Scientific Literature