(6-chloro-4H-benzo[d][1,3]dioxin-8-yl)methyl thiomorpholine-4-carbodithioate

ID: ALA4096293

PubChem CID: 339725

Max Phase: Preclinical

Molecular Formula: C14H16ClNO2S3

Molecular Weight: 361.94

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  S=C(SCc1cc(Cl)cc2c1OCOC2)N1CCSCC1

Standard InChI:  InChI=1S/C14H16ClNO2S3/c15-12-5-10-7-17-9-18-13(10)11(6-12)8-21-14(19)16-1-3-20-4-2-16/h5-6H,1-4,7-9H2

Standard InChI Key:  RRGVLFNBDFONQD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    7.8734   -6.0374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8723   -6.8648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5870   -7.2776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5853   -5.6247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2998   -6.0332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3009   -6.8601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0137   -7.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7300   -6.8582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7288   -6.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0114   -5.6165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1575   -7.2767    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.5828   -4.7997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8671   -4.3893    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.8646   -3.5643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1490   -3.1539    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5779   -3.1497    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.1520   -2.3278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4404   -1.9175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7247   -2.3287    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.7252   -3.1546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4414   -3.5694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  2 11  1  0
  4 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 15 17  1  0
 15 21  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4096293

   (6-chloro-4H-1,3-benzodioxin-8-yl)methyl thiomorpholine-4-carbodithioate

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: 361.94

Molecular Weight (Monoisotopic): 361.0032

AlogP: 3.77

#Rotatable Bonds: 2

Polar Surface Area: 21.70

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.92

CX LogD: 3.92

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.74

Np Likeness Score: -1.87

References

1. Ballante F, Reddy DR, Zhou NJ, Marshall GR..  (2017)  Structural insights of SmKDAC8 inhibitors: Targeting Schistosoma epigenetics through a combined structure-based 3D QSAR, in vitro and synthesis strategy.,  25  (7): [PMID:28259528] [10.1016/j.bmc.2017.02.020]

2. Johannes Zuegg, Alysha Elliott, Maite Amado, Emma Cowie, Ali Hinton, Geraldine Kaeslin, Angela Kavanagh, Anne Kunert, Gabriell Lowe, Soumya Ramu, Janet Reid, Robin Trauer, Mathilde Desselle, Ruth Neale, Karl Hansford, Mark Blascovich, Matthew Cooper. CO-ADD screening of NIH NCI Diversity Set V,  [10.6019/CHEMBL4296182]

Source

Source(2):

• Scientific Literature
• CO-ADD antimicrobial screening data