((R)-1-((S)-2-(2,5-dichlorobenzamido)-3-methoxypropanamido)-3-methylbutyl)boronic acid

ID: ALA4243375

PubChem CID: 145983051

Max Phase: Preclinical

Molecular Formula: C16H23BCl2N2O5

Molecular Weight: 405.09

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC[C@H](NC(=O)c1cc(Cl)ccc1Cl)C(=O)N[C@@H](CC(C)C)B(O)O

Standard InChI:  InChI=1S/C16H23BCl2N2O5/c1-9(2)6-14(17(24)25)21-16(23)13(8-26-3)20-15(22)11-7-10(18)4-5-12(11)19/h4-5,7,9,13-14,24-25H,6,8H2,1-3H3,(H,20,22)(H,21,23)/t13-,14-/m0/s1

Standard InChI Key:  QZRBBSWQICQORE-KBPBESRZSA-N

Molfile:  

     RDKit          2D

 26 26  0  0  0  0  0  0  0  0999 V2000
   23.9448   -3.8754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9436   -4.6950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6517   -5.1039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3613   -4.6945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3585   -3.8718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6499   -3.4666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0647   -3.4606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7739   -3.8665    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.0616   -2.6434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.4801   -3.4552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1893   -3.8612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8955   -3.4499    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.1924   -4.6783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.6047   -3.8558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3109   -3.4446    0.0000 B   0  0  0  0  0  0  0  0  0  0  0  0
   29.6078   -4.6730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3170   -5.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3201   -5.8961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0232   -4.6677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0201   -3.8505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.3078   -2.6274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.4770   -2.6381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1832   -2.2268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.1801   -1.4096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6474   -2.6494    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   24.6515   -5.9211    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  5  7  1  0
  7  8  1  0
  7  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 12 14  1  0
 14 15  1  0
 14 16  1  6
 16 17  1  0
 17 18  1  0
 17 19  1  0
 15 20  1  0
 15 21  1  0
 10 22  1  1
 22 23  1  0
 23 24  1  0
  6 25  1  0
  3 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4243375

   ---

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: 405.09

Molecular Weight (Monoisotopic): 404.1077

AlogP: ┄

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HBA: ┄

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#RO5 Violations: ┄

HBA (Lipinski): ┄

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: ┄

CX LogD: ┄

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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