2,2'-(Pentane-1,5-diylbis(azanediyl))bis(benzo[d]isothiazol-3(2H)-one)

ID: ALA4536072

PubChem CID: 155548628

Max Phase: Preclinical

Molecular Formula: C19H20N4O2S2

Molecular Weight: 400.53

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=c1c2ccccc2sn1NCCCCCNn1sc2ccccc2c1=O

Standard InChI:  InChI=1S/C19H20N4O2S2/c24-18-14-8-2-4-10-16(14)26-22(18)20-12-6-1-7-13-21-23-19(25)15-9-3-5-11-17(15)27-23/h2-5,8-11,20-21H,1,6-7,12-13H2

Standard InChI Key:  PARNJTDMQCVLCM-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   12.3709  -11.9837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0789  -12.3926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0771  -10.7553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7857  -11.1605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7860  -11.9837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5690  -12.2379    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.0527  -11.5717    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5686  -10.9060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8208  -10.1246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8699  -11.5714    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.2787  -12.2790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0959  -12.2787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5047  -12.9863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3219  -12.9860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7308  -13.6936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5480  -13.6933    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.9563  -12.9854    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.7675  -12.8986    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.6223  -12.2379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8228  -12.0688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2293  -11.6908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9325  -12.0991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6356  -11.6943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6367  -10.8814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9288  -10.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2286  -10.8821    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
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9  5  1  0
  9 10  2  0
  8 11  1  0
 11 12  1  0
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 19 23  1  0
 22 20  1  0
 20 18  1  0
 20 21  2  0
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 23 24  1  0
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 25 26  1  0
 26 27  2  0
 27 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4536072

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 400.53

Molecular Weight (Monoisotopic): 400.1028

AlogP: 3.40

#Rotatable Bonds: 8

Polar Surface Area: 68.06

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.58

CX LogP: 3.42

CX LogD: 3.42

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.44

Np Likeness Score: -0.46

References

1. Castelli R, Scalvini L, Vacondio F, Lodola A, Anselmi M, Vezzosi S, Carmi C, Bassi M, Ferlenghi F, Rivara S, Møller IR, Rand KD, Daglian J, Wei D, Dotsey EY, Ahmed F, Jung KM, Stella N, Singh S, Mor M, Piomelli D..  (2020)  Benzisothiazolinone Derivatives as Potent Allosteric Monoacylglycerol Lipase Inhibitors That Functionally Mimic Sulfenylation of Regulatory Cysteines.,  63  (3): [PMID:31714779] [10.1021/acs.jmedchem.9b01679]

Source

Source(1):

• Scientific Literature