3-(4-((4-bromophenylthio)methyl)benzamido)benzoic acid

ID: ALA597975

PubChem CID: 1355953

Max Phase: Preclinical

Molecular Formula: C21H16BrNO3S

Molecular Weight: 442.33

Molecule Type: Small molecule

Names and Identifiers

Synonyms: ZINC 01196449 | CHEMBL597975|ZINC 01196449|CCG-3541|BDBM50481417

Canonical SMILES:  O=C(O)c1cccc(NC(=O)c2ccc(CSc3ccc(Br)cc3)cc2)c1

Standard InChI:  InChI=1S/C21H16BrNO3S/c22-17-8-10-19(11-9-17)27-13-14-4-6-15(7-5-14)20(24)23-18-3-1-2-16(12-18)21(25)26/h1-12H,13H2,(H,23,24)(H,25,26)

Standard InChI Key:  DDWIAVFPVNJBQW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    1.5415   -8.8708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2560   -9.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2560  -10.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5415  -10.5208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8270  -10.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8270   -9.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5415   -8.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2560   -7.6333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8270   -7.6333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1126  -10.5208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1126  -11.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6019  -11.7583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8270  -11.7583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6019  -12.5833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3164  -12.9958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0308  -12.5833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0308  -11.7583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3164  -11.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7453  -12.9958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7453  -13.8208    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4598  -14.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4598  -15.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1742  -15.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8887  -15.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8887  -14.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1742  -13.8208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6032  -15.4708    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
 12 14  2  0
  1  7  1  0
 14 15  1  0
  3  4  2  0
 15 16  2  0
  7  8  2  0
 16 17  1  0
 17 18  2  0
 18 12  1  0
  7  9  1  0
 16 19  1  0
  4  5  1  0
 19 20  1  0
  5 10  1  0
 20 21  1  0
  2  3  1  0
 21 22  2  0
 10 11  1  0
 22 23  1  0
  5  6  2  0
 23 24  2  0
 11 12  1  0
 24 25  1  0
  6  1  1  0
 25 26  2  0
 26 21  1  0
 11 13  2  0
 24 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA597975

   3-[[4-[(4-Bromophenyl)sulfanylmethyl]benzoyl]amino]benzoic acid

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: 442.33

Molecular Weight (Monoisotopic): 441.0034

AlogP: 5.69

#Rotatable Bonds: 6

Polar Surface Area: 66.40

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.92

CX Basic pKa: ┄

CX LogP: 5.74

CX LogD: 2.54

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.48

Np Likeness Score: -1.42

References

1. Podvinec M, Lim SP, Schmidt T, Scarsi M, Wen D, Sonntag LS, Sanschagrin P, Shenkin PS, Schwede T..  (2010)  Novel inhibitors of dengue virus methyltransferase: discovery by in vitro-driven virtual screening on a desktop computer grid.,  53  (4): [PMID:20108931] [10.1021/jm900776m]

Source

Source(1):

• Scientific Literature