6-((2-chloro-10H-phenothiazin-10-yl)methyl)-1,3,5-triazine-2,4-diamine

ID: ALA1099319

PubChem CID: 46888180

Max Phase: Preclinical

Molecular Formula: C16H13ClN6S

Molecular Weight: 356.84

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(N)nc(CN2c3ccccc3Sc3ccc(Cl)cc32)n1

Standard InChI:  InChI=1S/C16H13ClN6S/c17-9-5-6-13-11(7-9)23(10-3-1-2-4-12(10)24-13)8-14-20-15(18)22-16(19)21-14/h1-7H,8H2,(H4,18,19,20,21,22)

Standard InChI Key:  QEXQZWNRCYXEBK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   12.1065    0.0418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1053   -0.7878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8220   -1.2018    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.5404   -0.7873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5375    0.0454    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8202    0.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3885   -1.2009    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8178    1.2830    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2575   -1.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9732   -0.7850    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4052    0.0356    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.9684    0.0374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6872    0.4467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6910    1.2719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9768    1.6887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2575    1.2744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2571    0.4505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4022   -0.7920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6888   -1.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6864   -2.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3966   -2.4329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1107   -2.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1097   -1.2014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3955   -3.2601    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
 18 11  1  0
 11 13  1  0
  5  6  2  0
  6  1  1  0
 12 13  2  0
  1  2  2  0
 13 14  1  0
  2  7  1  0
 14 15  2  0
  3  4  2  0
 15 16  1  0
  6  8  1  0
 16 17  2  0
 17 12  1  0
  4  9  1  0
 18 19  2  0
  4  5  1  0
 19 20  1  0
  9 10  1  0
 20 21  2  0
 10 19  1  0
 21 22  1  0
  2  3  1  0
 22 23  2  0
 23 18  1  0
 10 12  1  0
 21 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1099319

   6-[(2-Chlorophenothiazin-10-yl)methyl]-1,3,5-triazine-2,4-diamine

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: 356.84

Molecular Weight (Monoisotopic): 356.0611

AlogP: 3.49

#Rotatable Bonds: 2

Polar Surface Area: 93.95

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.69

CX LogP: 4.13

CX LogD: 4.13

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.73

Np Likeness Score: -1.56

References

1. Bag S, Tawari NR, Degani MS, Queener SF..  (2010)  Design, synthesis, biological evaluation and computational investigation of novel inhibitors of dihydrofolate reductase of opportunistic pathogens.,  18  (9): [PMID:20363634] [10.1016/j.bmc.2010.03.031]

Source

Source(1):

• Scientific Literature