(rac)-N-{4-[(6-methyl-2,3,4,5-tetrahydro-1,5-benzothiazepin-5-yl)carbonyl]phenyl}-2-methylbenzamide

ID: ALA3416767

PubChem CID: 118734334

Max Phase: Preclinical

Molecular Formula: C25H24N2O2S

Molecular Weight: 416.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccccc1C(=O)Nc1ccc(C(=O)N2CCCSc3cccc(C)c32)cc1

Standard InChI:  InChI=1S/C25H24N2O2S/c1-17-7-3-4-9-21(17)24(28)26-20-13-11-19(12-14-20)25(29)27-15-6-16-30-22-10-5-8-18(2)23(22)27/h3-5,7-14H,6,15-16H2,1-2H3,(H,26,28)

Standard InChI Key:  LQCRQEJXMNDRFQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
   -1.4884   -1.5247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4637    6.8428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5483    5.6545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7442   -1.6517    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9829    3.2321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6064    4.0689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1195    4.2676    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
    3.2904    9.2218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9505    6.6441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5218    5.2572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1007    9.3787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4432   11.9585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5481   12.9878    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
    2.9404    0.0000    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
    3.6326   11.7995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2069    3.0761    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
    6.6062   11.4023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0348   12.7892    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
    4.2039   10.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6908   10.2140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8640    7.8349    0.0000 N   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
    2.2325   -1.4158    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
   -1.5141    2.7244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 18 13  1  0
 20 19  1  0
 29  1  2  0
 25 24  1  0
 28 16  1  0
  9 24  1  0
  8 15  2  0
  3  7  1  0
 23 29  1  0
 21 25  2  0
  4 28  1  0
  1  8  1  0
  6 11  1  0
  7  6  2  0
 15 27  1  0
 11 10  2  0
 23 20  1  0
 19  5  2  0
 18 14  1  0
 20 17  1  0
 22 21  1  0
 24 18  2  0
  2  3  2  0
 10 26  1  0
 17 16  1  0
  9 12  2  0
 27 23  2  0
 26  9  1  0
 29  4  1  0
 14 22  2  0
 19  7  1  0
 10  2  1  0
 27 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3416767

   ---

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: 416.55

Molecular Weight (Monoisotopic): 416.1558

AlogP: 5.70

#Rotatable Bonds: 3

Polar Surface Area: 49.41

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.46

CX LogD: 5.46

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.60

Np Likeness Score: -1.68

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]

Source

Source(1):

• Scientific Literature