2-(Phenyl)-4-(3'-hydroxyphenyl)-2,3-dihydro-1,5-benzothiazepine

ID: ALA456156

PubChem CID: 44587921

Max Phase: Preclinical

Molecular Formula: C21H17NOS

Molecular Weight: 331.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Oc1cccc(C2=Nc3ccccc3SC(c3ccccc3)C2)c1

Standard InChI:  InChI=1S/C21H17NOS/c23-17-10-6-9-16(13-17)19-14-21(15-7-2-1-3-8-15)24-20-12-5-4-11-18(20)22-19/h1-13,21,23H,14H2

Standard InChI Key:  DZJYISGBNCCXKA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   -1.7559    1.4240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1461    0.6955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4966    0.7559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9345    1.4529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7095   -0.0094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8848    0.0227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3396   -0.6046    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2004   -0.6800    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4864   -1.4193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9814   -1.4812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2180   -1.8073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6933   -1.8980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4096   -1.4883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1204   -1.9038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1161   -2.7286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3951   -3.1363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6872   -2.7186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8361   -1.4954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2329   -1.8151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2463   -2.6401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9665   -3.0391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6735   -2.6143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6561   -1.7862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9354   -1.3909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  2  0
 12 13  2  0
  6  3  1  0
 13 14  1  0
  6  7  1  0
 14 15  2  0
  1  2  2  0
 15 16  1  0
  5  8  1  0
 16 17  2  0
 17 12  1  0
 10 12  1  0
  3  4  2  0
 14 18  1  0
  7  9  1  0
  4  1  1  0
 19 20  2  0
  8 10  2  0
 20 21  1  0
  2  5  1  0
 21 22  2  0
  9 11  1  0
 22 23  1  0
 10 11  1  0
 23 24  2  0
 24 19  1  0
  9 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA456156

   2-(Phenyl)-4-(3''-hydroxyphenyl)-2,3-dihydro-1,5-benzothiazepine

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: 331.44

Molecular Weight (Monoisotopic): 331.1031

AlogP: 5.75

#Rotatable Bonds: 2

Polar Surface Area: 32.59

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.18

CX Basic pKa: 1.11

CX LogP: 5.53

CX LogD: 5.47

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.65

Np Likeness Score: -0.47

References

1. Ansari FL, Iftikhar F, Ihsan-Ul-Haq, Mirza B, Baseer M, Rashid U..  (2008)  Solid-phase synthesis and biological evaluation of a parallel library of 2,3-dihydro-1,5-benzothiazepines.,  16  (16): [PMID:18650096] [10.1016/j.bmc.2008.07.009]

2. Ansari FL, Kalsoom S, Zaheer-ul-Haq, Ali Z, Jabeen F.  (2012)  In silico studies on 2,3-dihydro-1,5-benzothiazepines as cholinesterase inhibitors,  21  (9): [10.1007/s00044-011-9754-6]

3. Jabeen F, Oliferenko PV, Oliferenko AA, Pillai GG, Ansari FL, Hall CD, Katritzky AR..  (2014)  Dual inhibition of the α-glucosidase and butyrylcholinesterase studied by molecular field topology analysis.,  80  [PMID:24780600] [10.1016/j.ejmech.2014.04.018]

Source

Source(1):

• Scientific Literature