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

ID: ALA4174777

PubChem CID: 11090180

Max Phase: Preclinical

Molecular Formula: C15H18N6O2S2

Molecular Weight: 378.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NS(=O)(=O)N1CCN(Cc2ccc3c(c2)Nc2nccnc2S3)CC1

Standard InChI:  InChI=1S/C15H18N6O2S2/c16-25(22,23)21-7-5-20(6-8-21)10-11-1-2-13-12(9-11)19-14-15(24-13)18-4-3-17-14/h1-4,9H,5-8,10H2,(H,17,19)(H2,16,22,23)

Standard InChI Key:  CRLHHGFSDDNERW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   23.9338   -3.7888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.5293   -3.0830    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   23.1204   -3.7862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0732   -1.8696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0721   -2.6891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7801   -3.0981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7783   -1.4607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4869   -1.8660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4858   -2.6866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1920   -3.0957    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   29.1943   -1.4544    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.9003   -1.8613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9033   -2.6850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6170   -3.0925    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.3282   -2.6773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3212   -1.8505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6069   -1.4468    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.3654   -1.4612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6578   -1.8699    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.9520   -1.4567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2465   -1.8620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2425   -2.6795    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.9502   -3.0901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6618   -2.6832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8271   -2.6745    0.0000 N   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
M  END

Alternative Forms

1. Parent:

   

   ALA4174777

   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: 378.48

Molecular Weight (Monoisotopic): 378.0933

AlogP: 1.01

#Rotatable Bonds: 3

Polar Surface Area: 104.45

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.40

CX Basic pKa: 5.67

CX LogP: 0.44

CX LogD: 0.43

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.70

Np Likeness Score: -1.55

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