6-(1-Adamantyl-1-hydroxyiminomethyl)-3-pentylbenzo[d]thiazol-2(3H)-one

ID: ALA4539849

PubChem CID: 155549880

Max Phase: Preclinical

Molecular Formula: C23H30N2O2S

Molecular Weight: 398.57

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCCCn1c(=O)sc2cc(/C(=N\O)C34CC5CC(CC(C5)C3)C4)ccc21

Standard InChI:  InChI=1S/C23H30N2O2S/c1-2-3-4-7-25-19-6-5-18(11-20(19)28-22(25)26)21(24-27)23-12-15-8-16(13-23)10-17(9-15)14-23/h5-6,11,15-17,27H,2-4,7-10,12-14H2,1H3/b24-21+

Standard InChI Key:  VTQGNKUZJLDWLY-DARPEHSRSA-N

Molfile:  

 
     RDKit          2D

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   24.5087  -28.6871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2168  -29.0961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2150  -27.4587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9236  -27.8640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9284  -28.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7084  -28.9310    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   27.1858  -28.2659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7007  -27.6065    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.0030  -28.2611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.8007  -29.0951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0933  -28.6860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8001  -29.9123    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.0169  -29.2867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6521  -28.6096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8096  -29.0638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3526  -28.8697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5593  -29.3637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8070  -28.2235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3583  -27.5677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6476  -27.8217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1032  -27.8748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6949  -26.7857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3997  -26.3680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1103  -26.7757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8151  -26.3622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5257  -26.7658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5075  -30.3215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
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  9 23  1  0
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 24 25  1  0
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 26 27  1  0
 13 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4539849

   ---

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: 398.57

Molecular Weight (Monoisotopic): 398.2028

AlogP: 5.65

#Rotatable Bonds: 6

Polar Surface Area: 54.59

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 6.48

CX Basic pKa: 2.14

CX LogP: 5.79

CX LogD: 4.84

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.30

Np Likeness Score: -0.89

References

1. Leleu-Chavain N, Baudelet D, Heloire VM, Rocha DE, Renault N, Barczyk A, Djouina M, Body-Malapel M, Carato P, Millet R..  (2019)  Benzo[d]thiazol-2(3H)-ones as new potent selective CB₂ agonists with anti-inflammatory properties.,  165  [PMID:30583970] [10.1016/j.ejmech.2018.12.008]

Source

Source(1):

• Scientific Literature