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

ID: ALA4215727

PubChem CID: 145972094

Max Phase: Preclinical

Molecular Formula: C21H16ClN3O4S

Molecular Weight: 441.90

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1ccc(CN2C(=O)c3ccc(Cl)cc3NC(=O)[C@H]2Cc2nccs2)cc1

Standard InChI:  InChI=1S/C21H16ClN3O4S/c22-14-5-6-15-16(9-14)24-19(26)17(10-18-23-7-8-30-18)25(20(15)27)11-12-1-3-13(4-2-12)21(28)29/h1-9,17H,10-11H2,(H,24,26)(H,28,29)/t17-/m1/s1

Standard InChI Key:  ADZXNDAYWRNAKE-QGZVFWFLSA-N

Molfile:  

     RDKit          2D

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   20.9425  -24.2245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7410  -22.8721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8540  -26.4054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0960  -22.3577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6670  -21.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7282  -21.9452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9712  -25.5145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3684  -27.0504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6670  -22.3577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0382  -26.5284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7410  -21.0183    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.7583  -24.1015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9525  -21.1203    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   21.9032  -21.9452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2726  -24.7465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0597  -20.5569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5453  -21.2019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0960  -21.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3815  -21.1203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5453  -22.6885    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.1554  -25.6374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0597  -23.3335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5574  -23.6764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3815  -22.7702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6411  -24.9924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1368  -22.6530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8089  -23.3969    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.4162  -23.9438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1239  -23.5351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9539  -22.7359    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  9 24  1  0
 17 16  2  0
 12 15  2  0
  2 20  1  0
  4  2  1  0
  3 10  1  0
  5  9  2  0
 11 17  1  0
 14  6  1  1
 21  3  1  0
  2 23  2  0
 25  1  2  0
 18 19  2  0
  5 13  1  0
 18 11  1  0
  4 18  1  0
 20 22  1  0
  7 21  2  0
  3  8  2  0
 15  7  1  0
 20 14  1  0
 17 14  1  0
 19  5  1  0
 21 25  1  0
  1 12  1  0
 24  4  2  0
 22 12  1  0
  6 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4215727

   ---

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: 441.90

Molecular Weight (Monoisotopic): 441.0550

AlogP: 3.70

#Rotatable Bonds: 5

Polar Surface Area: 99.60

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.08

CX Basic pKa: 2.46

CX LogP: 3.61

CX LogD: 0.63

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.63

Np Likeness Score: -1.02

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