SID99356395

ID: ALA1878187

Cas Number: 36110-11-9

PubChem CID: 294721

Max Phase: Preclinical

Molecular Formula: C12H12Cl2N2O7S

Molecular Weight: 399.21

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)CC1(C(=O)OC)Nc2cc(Cl)c(Cl)cc2S(=O)(=O)N1O

Standard InChI:  InChI=1S/C12H12Cl2N2O7S/c1-22-10(17)5-12(11(18)23-2)15-8-3-6(13)7(14)4-9(8)24(20,21)16(12)19/h3-4,15,19H,5H2,1-2H3

Standard InChI Key:  HXJIDAFJSVKUFH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
    1.8870   -0.9999    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.8870    0.6501    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.9709   -0.9999    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5012   -1.6319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4406   -1.6319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3999   -0.9999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8972    0.9949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9471   -0.4332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9108    1.6945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1724    2.3653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6854   -0.5874    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9709    0.6501    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6854    0.2376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2564   -0.5874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2564    0.2376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5099    0.2664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1226    0.9373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4580   -0.9999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4580    0.6501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1725   -0.5874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1725    0.2376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7353    1.6657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4600    1.6945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5234    2.4229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 20  1  0
  2 21  1  0
  3  4  2  0
  3  5  2  0
  3 11  1  0
  3 14  1  0
  6 11  1  0
  7 16  1  0
  7 23  1  0
  8 16  2  0
  9 22  1  0
  9 24  1  0
 10 22  2  0
 11 13  1  0
 12 13  1  0
 12 15  1  0
 13 16  1  0
 13 17  1  0
 14 15  1  0
 14 18  2  0
 15 19  2  0
 17 22  1  0
 18 20  1  0
 19 21  1  0
 20 21  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1878187

   2H-1,2,4-Benzothiadiazine-3-acetic acid, 6,7-dichloro-3,4-dihydro-2-hydroxy-3-(methoxycarbonyl)-, methyl ester, 1,1-dioxide

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: 399.21

Molecular Weight (Monoisotopic): 397.9742

AlogP: 1.23

#Rotatable Bonds: 3

Polar Surface Area: 122.24

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.79

CX Basic pKa: ┄

CX LogP: 1.66

CX LogD: 0.79

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.73

Np Likeness Score: 0.06

References

1. PubChem BioAssay data set, 

2. Tomek P, Palmer BD, Flanagan JU, Sun C, Raven EL, Ching LM..  (2017)  Discovery and evaluation of inhibitors to the immunosuppressive enzyme indoleamine 2,3-dioxygenase 1 (IDO1): Probing the active site-inhibitor interactions.,  126  [PMID:28011425] [10.1016/j.ejmech.2016.12.029]

3. 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]

4.  (2018)  INHIBITORS OF SARM1 NADase ACTIVITY AND USES THEREOF, 

Source

Source(4):

• Scientific Literature
• PubChem BioAssays
• Patent Bioactivity Data
• CO-ADD antimicrobial screening data