(R)-4-((3-(3,4-dichlorobenzyl)-8-methyl-2,5-dioxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-4(5H)-yl)methyl)benzoic acid

ID: ALA4208141

PubChem CID: 132213530

Max Phase: Preclinical

Molecular Formula: C25H20Cl2N2O4

Molecular Weight: 483.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc2c(c1)NC(=O)[C@@H](Cc1ccc(Cl)c(Cl)c1)N(Cc1ccc(C(=O)O)cc1)C2=O

Standard InChI:  InChI=1S/C25H20Cl2N2O4/c1-14-2-8-18-21(10-14)28-23(30)22(12-16-5-9-19(26)20(27)11-16)29(24(18)31)13-15-3-6-17(7-4-15)25(32)33/h2-11,22H,12-13H2,1H3,(H,28,30)(H,32,33)/t22-/m1/s1

Standard InChI Key:  DUMPLTNFAKUEPN-JOCHJYFZSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
    4.5589  -10.5321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5589  -11.3571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2734  -11.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2734  -10.1196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9878  -11.3571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.6328  -10.0177    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6328  -11.8715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4372  -10.2013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4372  -11.6879    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7951  -10.9446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9515   -9.5563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4493  -12.6758    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8444  -10.1196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6201  -10.9446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.1645  -13.7459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8631  -14.5139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0473  -14.6368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5329  -13.9918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8344  -13.2238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7459  -15.4048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9301  -15.5277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2603  -16.0498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8576  -11.6591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2701  -12.3735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8576  -13.0880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0326  -13.0880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6201  -12.3735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2701  -13.8025    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.0951  -12.3735    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  5  2  0
  6  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  5  8  1  0
  7  9  1  0
  8 10  1  0
  9 11  1  0
 10 11  1  0
  9 12  2  0
  8 13  2  0
  1 14  1  0
 11 15  1  1
 15 16  1  0
 10 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
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 21 22  1  0
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 21 24  1  0
 24 25  1  0
 24 26  2  0
 16 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 16  1  0
 29 32  1  0
 28 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4208141

   ---

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: 483.35

Molecular Weight (Monoisotopic): 482.0800

AlogP: 5.21

#Rotatable Bonds: 5

Polar Surface Area: 86.71

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.07

CX Basic pKa: ┄

CX LogP: 6.19

CX LogD: 3.07

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.52

Np Likeness Score: -0.57

References

1. Letourneau JJ, Stroke IL, Hilbert DW, Sturzenbecker LJ, Marinelli BA, Quintero JG, Sabalski J, Ma L, Diller DJ, Stein PD, Webb ML..  (2018)  Identification and initial optimization of inhibitors of Clostridium difficile (C. difficile) toxin B (TcdB).,  28  (4): [PMID:29331267] [10.1016/j.bmcl.2018.01.005]

Source

Source(1):

• Scientific Literature