4-(10H-9-Thia-1,4,10-triaza-anthracen-6-ylmethyl)-piperazine-1-sulfonic acid dimethylamide

ID: ALA4175184

PubChem CID: 11080019

Max Phase: Preclinical

Molecular Formula: C17H22N6O2S2

Molecular Weight: 406.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)S(=O)(=O)N1CCN(Cc2ccc3c(c2)Nc2nccnc2S3)CC1

Standard InChI:  InChI=1S/C17H22N6O2S2/c1-21(2)27(24,25)23-9-7-22(8-10-23)12-13-3-4-15-14(11-13)20-16-17(26-15)19-6-5-18-16/h3-6,11H,7-10,12H2,1-2H3,(H,18,20)

Standard InChI Key:  MCEWLKOJLFUUNZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   34.9329   -3.0170    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   34.5239   -3.7202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.4767   -1.8036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4756   -2.6231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1836   -3.0321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1818   -1.3947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8905   -1.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8893   -2.6206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.5955   -3.0297    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   40.5978   -1.3884    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.3039   -1.7953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3069   -2.6190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.0206   -3.0264    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.7317   -2.6113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.7247   -1.7845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.0105   -1.3808    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.7689   -1.3951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0613   -1.8039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.3556   -1.3907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6501   -1.7960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6460   -2.6135    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.3537   -3.0241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0654   -2.6172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2306   -2.6085    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.2333   -1.7913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5216   -3.0148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  2  0
  5  6  1  0
  6  9  2  0
  8  7  2  0
  7  4  1  0
  8  9  1  0
  8 11  1  0
  9 10  1  0
 10 13  1  0
 12 11  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
  4 18  1  0
 18 19  1  0
 19 20  1  0
 19 24  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 22  2  1  0
  2 25  1  0
 25 26  1  0
 25 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4175184

   N,N-dimethyl-4-(10H-pyrazino[2,3-b][1,4]benzothiazin-8-ylmethyl)piperazine-1-sulfonamide

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: 406.54

Molecular Weight (Monoisotopic): 406.1246

AlogP: 1.61

#Rotatable Bonds: 4

Polar Surface Area: 81.67

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.84

CX Basic pKa: 5.63

CX LogP: 0.88

CX LogD: 0.88

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.70

Np Likeness Score: -1.67

References

1. Pluta K, Jeleń M, Morak-Młodawska B, Zimecki M, Artym J, Kocięba M, Zaczyńska E..  (2017)  Azaphenothiazines - promising phenothiazine derivatives. An insight into nomenclature, synthesis, structure elucidation and biological properties.,  138  [PMID:28734245] [10.1016/j.ejmech.2017.07.009]

Source

Source(1):

• Scientific Literature