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

ID: ALA4205987

PubChem CID: 145975887

Max Phase: Preclinical

Molecular Formula: C21H21ClN2O4

Molecular Weight: 400.86

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)C[C@@H]1C(=O)Nc2cc(Cl)ccc2C(=O)N1Cc1ccc(C(=O)O)cc1

Standard InChI:  InChI=1S/C21H21ClN2O4/c1-12(2)9-18-19(25)23-17-10-15(22)7-8-16(17)20(26)24(18)11-13-3-5-14(6-4-13)21(27)28/h3-8,10,12,18H,9,11H2,1-2H3,(H,23,25)(H,27,28)/t18-/m1/s1

Standard InChI Key:  BSEDUPUIJSQEOK-GOSISDBHSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   14.6602  -26.0211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4355  -31.8926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2241  -30.4607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5780  -28.1021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5531  -26.5901    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   15.7480  -28.1109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3489  -26.4872    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2747  -27.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7057  -27.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6129  -32.0228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5297  -29.6963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5511  -30.9897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3523  -29.5786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9924  -26.5901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3390  -28.8323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3313  -27.4027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1489  -28.1577    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.8609  -30.2294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5063  -27.4110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6620  -28.8142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9482  -32.5351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7057  -27.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1635  -29.1515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3489  -28.3390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1489  -26.6726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7369  -31.1115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9924  -28.2402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2747  -27.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2 10  1  0
 25  1  2  0
 13 18  2  0
  6  4  1  0
  7 25  1  0
  3 11  2  0
  9  7  1  0
  8  5  1  0
 18 12  1  0
  8 28  2  0
 22 24  1  0
 26  3  1  0
 11 13  1  0
 25 19  1  0
 22  9  1  0
 12 26  2  0
 17 19  1  0
 24 23  2  0
 17 20  1  0
 26  2  1  0
 28 27  1  0
 14  8  1  0
 20 13  1  0
  6 15  1  0
  9 14  2  0
 24 17  1  0
 16  6  1  0
  2 21  2  0
 27 22  2  0
 19 16  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4205987

   ---

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: 400.86

Molecular Weight (Monoisotopic): 400.1190

AlogP: 4.05

#Rotatable Bonds: 5

Polar Surface Area: 86.71

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.07

CX Basic pKa: ┄

CX LogP: 4.67

CX LogD: 1.55

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.79

Np Likeness Score: -0.41

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