SID104224196

ID: ALA2141221

PubChem CID: 49853075

Max Phase: Preclinical

Molecular Formula: C18H19F3N4S

Molecular Weight: 380.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccnc(NC(=S)N2CCN(c3ccc(C(F)(F)F)cc3)CC2)c1

Standard InChI:  InChI=1S/C18H19F3N4S/c1-13-6-7-22-16(12-13)23-17(26)25-10-8-24(9-11-25)15-4-2-14(3-5-15)18(19,20)21/h2-7,12H,8-11H2,1H3,(H,22,23,26)

Standard InChI Key:  CDHYMMSTDFXWEP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    1.4268    1.5900    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9783   -1.4036    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2797   -2.5267    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1560   -2.8275    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7140   -0.4680    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7149    0.3570    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1391    0.3570    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5652    0.3553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4263   -0.8795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8552   -1.7045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5674   -2.1153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4268    0.7678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1407   -0.4670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4263   -1.7045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7140    0.3570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0004   -0.8805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8552   -0.8795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1407   -2.1170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7149   -0.4680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0004    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8508    0.7678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8508    1.5928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5652    2.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2797    0.7678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2797    1.5928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5652    2.8275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 12  2  0
  2 11  1  0
  3 11  1  0
  4 11  1  0
  5  9  1  0
  5 15  1  0
  5 16  1  0
  6 12  1  0
  6 19  1  0
  6 20  1  0
  7 12  1  0
  7 21  1  0
  8 21  2  0
  8 24  1  0
  9 13  2  0
  9 14  1  0
 10 11  1  0
 10 17  2  0
 10 18  1  0
 13 17  1  0
 14 18  2  0
 15 20  1  0
 16 19  1  0
 21 22  1  0
 22 23  2  0
 23 25  1  0
 23 26  1  0
 24 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2141221

   N-(4-methylpyridin-2-yl)-4-[4-(trifluoromethyl)phenyl]piperazine-1-carbothioamide

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: 380.44

Molecular Weight (Monoisotopic): 380.1283

AlogP: 3.93

#Rotatable Bonds: 2

Polar Surface Area: 31.40

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.80

CX LogP: 4.72

CX LogD: 4.72

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.80

Np Likeness Score: -1.94

References

1. PubChem BioAssay data set, 

2. Foley TL, Rai G, Yasgar A, Daniel T, Baker HL, Attene-Ramos M, Kosa NM, Leister W, Burkart MD, Jadhav A, Simeonov A, Maloney DJ..  (2014)  4-(3-Chloro-5-(trifluoromethyl)pyridin-2-yl)-N-(4-methoxypyridin-2-yl)piperazine-1-carbothioamide (ML267), a potent inhibitor of bacterial phosphopantetheinyl transferase that attenuates secondary metabolism and thwarts bacterial growth.,  57  (3): [PMID:24450337] [10.1021/jm401752p]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays