(R)-4-((8-chloro-2,5-dioxo-3-(pyridin-2-ylmethyl)-2,3-dihydro-1H-benzo[e][1,4]diazepin-4(5H)-yl)methyl)-N-(5-methoxypyridin-2-yl)-2-methylbenzamide

ID: ALA4472977

PubChem CID: 132213664

Max Phase: Preclinical

Molecular Formula: C30H26ClN5O4

Molecular Weight: 556.02

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(NC(=O)c2ccc(CN3C(=O)c4ccc(Cl)cc4NC(=O)[C@H]3Cc3ccccn3)cc2C)nc1

Standard InChI:  InChI=1S/C30H26ClN5O4/c1-18-13-19(6-9-23(18)28(37)35-27-11-8-22(40-2)16-33-27)17-36-26(15-21-5-3-4-12-32-21)29(38)34-25-14-20(31)7-10-24(25)30(36)39/h3-14,16,26H,15,17H2,1-2H3,(H,34,38)(H,33,35,37)/t26-/m1/s1

Standard InChI Key:  BNRDHHALNBJGIK-AREMUKBSSA-N

Molfile:  

 
     RDKit          2D

 40 44  0  0  0  0  0  0  0  0999 V2000
   12.9498   -4.4863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9487   -5.3058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6567   -5.7148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6549   -4.0774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3646   -5.3012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3636   -4.4827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0055   -3.9658    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0109   -5.8127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8075   -4.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8130   -5.6256    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1647   -4.8811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8324   -6.6102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3139   -3.5004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9819   -4.8776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3874   -4.1681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3265   -6.2613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1404   -6.2610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2019   -4.1667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.6074   -3.4581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1956   -2.7512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3742   -2.7574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9725   -3.4666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5458   -6.9680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3589   -6.9681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7664   -6.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3548   -5.5554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5430   -5.5589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5836   -6.2611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9910   -5.5527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9934   -6.9681    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2420   -4.0778    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   20.8106   -6.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2156   -7.6731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0320   -7.6720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4402   -6.9631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0260   -6.2537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2109   -6.2583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.7675   -7.6758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2574   -6.9606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.6681   -7.6671    0.0000 C   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
  8 12  2  0
  9 13  2  0
 11 14  1  1
 14 15  1  0
 10 16  1  0
 16 17  1  0
 15 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 15  1  0
 17 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 17  1  0
 25 28  1  0
 28 29  2  0
 28 30  1  0
  1 31  1  0
 30 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 36  1  0
 36 37  2  0
 37 32  1  0
 24 38  1  0
 35 39  1  0
 39 40  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4472977

   ---

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: 556.02

Molecular Weight (Monoisotopic): 555.1673

AlogP: 4.91

#Rotatable Bonds: 7

Polar Surface Area: 113.52

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.25

CX Basic pKa: 4.53

CX LogP: 5.05

CX LogD: 5.05

Aromatic Rings: 4

Heavy Atoms: 40

QED Weighted: 0.34

Np Likeness Score: -1.34

References

1. Letourneau JJ, Stroke IL, Hilbert DW, Cole AG, Sturzenbecker LJ, Marinelli BA, Quintero JG, Sabalski J, Li Y, Ma L, Pechik I, Stein PD, Webb ML..  (2018)  Synthesis and SAR studies of novel benzodiazepinedione-based inhibitors of Clostridium difficile (C. difficile) toxin B (TcdB).,  28  (23-24): [PMID:30392779] [10.1016/j.bmcl.2018.10.047]

Source

Source(1):

• Scientific Literature