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

ID: ALA4571345

PubChem CID: 155562737

Max Phase: Preclinical

Molecular Formula: C24H33NO2S

Molecular Weight: 399.60

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C24H33NO2S/c1-3-4-5-8-25-20-7-6-19(12-21(20)28-23(25)26)22(27-2)24-13-16-9-17(14-24)11-18(10-16)15-24/h6-7,12,16-18,22H,3-5,8-11,13-15H2,1-2H3

Standard InChI Key:  LQUPDSZZPSGSPB-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   15.0079  -28.5798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7159  -28.9888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7141  -27.3514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4227  -27.7567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4275  -28.5753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2076  -28.8237    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.6849  -28.1586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1998  -27.4992    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5021  -28.1538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2998  -28.9878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5924  -28.5787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2992  -29.8050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5160  -29.1794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1512  -28.5023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3087  -28.9565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8517  -28.7624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0584  -29.2564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3061  -28.1162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8574  -27.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1468  -27.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6024  -27.7675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1940  -26.6784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8988  -26.2648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6094  -26.6684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3142  -26.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0248  -26.6585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0066  -30.2142    0.0000 C   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
 25 26  1  0
 26 27  1  0
 13 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4571345

   ---

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: 399.60

Molecular Weight (Monoisotopic): 399.2232

AlogP: 6.16

#Rotatable Bonds: 7

Polar Surface Area: 31.23

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.98

CX LogD: 5.98

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.52

Np Likeness Score: -0.69

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