6-Nitro-2-phenethylbenzo[d]isothiazol-3(2H)-one

ID: ALA4544505

PubChem CID: 155553071

Max Phase: Preclinical

Molecular Formula: C15H12N2O3S

Molecular Weight: 300.34

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=c1c2ccc([N+](=O)[O-])cc2sn1CCc1ccccc1

Standard InChI:  InChI=1S/C15H12N2O3S/c18-15-13-7-6-12(17(19)20)10-14(13)21-16(15)9-8-11-4-2-1-3-5-11/h1-7,10H,8-9H2

Standard InChI Key:  DXWDTZRLISMHBB-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
   23.3257  -16.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3245  -17.0767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0326  -17.4856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0308  -15.8483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7394  -16.2535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7397  -17.0767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5226  -17.3309    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   26.0063  -16.6647    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.5222  -15.9990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7745  -15.2217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.8235  -16.6644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2319  -15.9566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0491  -15.9563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4555  -16.6660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2719  -16.6661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6811  -15.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2678  -15.2478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4528  -15.2512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6167  -17.4889    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.9093  -17.0797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6161  -18.3061    0.0000 O   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
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 19 20  1  0
 19 21  2  0
  2 19  1  0
M  CHG  2  19   1  20  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4544505

   ---

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: 300.34

Molecular Weight (Monoisotopic): 300.0569

AlogP: 3.21

#Rotatable Bonds: 4

Polar Surface Area: 65.14

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.53

CX LogD: 3.53

Aromatic Rings: 3

Heavy Atoms: 21

QED Weighted: 0.55

Np Likeness Score: -1.27

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