rac-N-(4-(5,9-dimethyl-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepine-1-carbonyl)phenyl)-2-methylbenzamide

ID: ALA3416774

PubChem CID: 53349471

Max Phase: Preclinical

Molecular Formula: C26H27N3O2

Molecular Weight: 413.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccccc1C(=O)Nc1ccc(C(=O)N2CCCN(C)c3cccc(C)c32)cc1

Standard InChI:  InChI=1S/C26H27N3O2/c1-18-8-4-5-10-22(18)25(30)27-21-14-12-20(13-15-21)26(31)29-17-7-16-28(3)23-11-6-9-19(2)24(23)29/h4-6,8-15H,7,16-17H2,1-3H3,(H,27,30)

Standard InChI Key:  GCZOEWZYLOZOQU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
    2.2325   -1.4158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7320   -6.6842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1203   -3.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2507    1.3976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3830    2.8203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4679   -8.8325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4884   -1.5247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9888   -4.2426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4819   -4.0982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2251  -11.5630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9404    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3535  -10.3422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5141   -2.7244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.7623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9749   -8.9769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7442   -1.6517    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9651   -7.7403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4884    1.5247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3535   -5.3190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7182  -11.4185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7805    1.6880    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5955   -6.6642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8315    0.7623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3396  -10.0533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1003   -7.7572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0744   -3.1309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.7623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2390   -6.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6066   -7.9038    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3674   -5.6078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8315   -0.7623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 30  8  1  0
 24 20  2  0
 14 21  1  0
 15  6  2  0
  6 17  1  0
 12 15  1  0
  2 28  1  0
 18 23  1  0
  3  8  1  0
 14 18  2  0
 25 15  1  0
 21  5  1  0
 10 12  2  0
  1 11  1  0
 25 22  2  0
  8  9  2  0
  9 19  1  0
  2 29  1  0
 31  7  1  0
 27 14  1  0
 19  2  2  0
 28 30  2  0
 16  3  1  0
  6 24  1  0
 23 31  2  0
 21  4  1  0
 27 16  1  0
  7 27  2  0
  4 11  1  0
  3 26  2  0
 29 25  1  0
 16  1  1  0
  7 13  1  0
 20 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3416774

   N-[4-(1,6-dimethyl-3,4-dihydro-2H-1,5-benzodiazepine-5-carbonyl)phenyl]-2-methylbenzamide

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: 413.52

Molecular Weight (Monoisotopic): 413.2103

AlogP: 5.04

#Rotatable Bonds: 3

Polar Surface Area: 52.65

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 4.09

CX LogP: 5.04

CX LogD: 5.04

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.65

Np Likeness Score: -1.48

References

1. Yoneda T, Tabata H, Tasaka T, Oshitari T, Takahashi H, Natsugari H..  (2015)  N-benzoyl-1,5-benzothiazepine and its S-oxide as vasopressin receptor ligands: insight into the active stereochemistry around the seven-membered ring.,  58  (7): [PMID:25774991] [10.1021/acs.jmedchem.5b00289]

2. Yoneda T, Tabata H, Tasaka T, Oshitari T, Takahashi H, Natsugari H..  (2015)  N-benzoyl-1,5-benzothiazepine and its S-oxide as vasopressin receptor ligands: insight into the active stereochemistry around the seven-membered ring.,  58  (7): [PMID:25774991] [10.1021/acs.jmedchem.5b00289]

3. Yoneda T, Tabata H, Tasaka T, Oshitari T, Takahashi H, Natsugari H..  (2015)  N-benzoyl-1,5-benzothiazepine and its S-oxide as vasopressin receptor ligands: insight into the active stereochemistry around the seven-membered ring.,  58  (7): [PMID:25774991] [10.1021/acs.jmedchem.5b00289]

4. Glunz PW..  (2018)  Recent encounters with atropisomerism in drug discovery.,  28  (2.0): [PMID:29223590] [10.1016/j.bmcl.2017.11.050]

5. Glunz PW..  (2018)  Recent encounters with atropisomerism in drug discovery.,  28  (2.0): [PMID:29223590] [10.1016/j.bmcl.2017.11.050]

Source

Source(1):

• Scientific Literature