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

ID: ALA4210705

PubChem CID: 132214325

Max Phase: Preclinical

Molecular Formula: C24H19ClN2O5

Molecular Weight: 450.88

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1ccc(CN2C(=O)c3ccc(Cl)cc3NC(=O)[C@@H]2Cc2ccc(O)cc2)cc1

Standard InChI:  InChI=1S/C24H19ClN2O5/c25-17-7-10-19-20(12-17)26-22(29)21(11-14-3-8-18(28)9-4-14)27(23(19)30)13-15-1-5-16(6-2-15)24(31)32/h1-10,12,21,28H,11,13H2,(H,26,29)(H,31,32)/t21-/m0/s1

Standard InChI Key:  JRKRQDZUVCEFCE-NRFANRHFSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
    5.0676   -6.4764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0676   -7.3014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7821   -7.7139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7821   -6.0639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4965   -7.3014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4965   -6.4764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1415   -5.9620    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1415   -7.8158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9459   -6.1456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9459   -7.6322    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3038   -6.8889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4602   -5.5006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9580   -8.6201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3531   -6.0639    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.1288   -6.8889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5413   -7.6034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4602   -8.2772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1588   -9.0452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6732   -9.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3718  -10.4581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5560  -10.5811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0416   -9.9361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3430   -9.1681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2546  -11.3491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4388  -11.4720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7690  -11.9941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3663   -7.6034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7788   -8.3178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3663   -9.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5413   -9.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1288   -8.3178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7788   -9.7468    0.0000 O   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  6
 15 16  1  0
 10 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 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
M  END

Alternative Forms

1. Parent:

   

   ALA4210705

   ---

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: 450.88

Molecular Weight (Monoisotopic): 450.0982

AlogP: 3.95

#Rotatable Bonds: 5

Polar Surface Area: 106.94

Molecular Species: ACID

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.07

CX Basic pKa: ┄

CX LogP: 4.77

CX LogD: 1.64

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.55

Np Likeness Score: -0.26

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