6-chloro-N-[5-(cyclopentylmethylsulfanyl)-1,3,4-thiadiazol-2-yl]-1,3-benzodioxole-5-carboxamide

ID: ALA5289614

Max Phase: Preclinical

Molecular Formula: C16H16ClN3O3S2

Molecular Weight: 397.91

Names and Identifiers

Canonical SMILES:  O=C(Nc1nnc(SCC2CCCC2)s1)c1cc2c(cc1Cl)OCO2

Standard InChI:  InChI=1S/C16H16ClN3O3S2/c17-11-6-13-12(22-8-23-13)5-10(11)14(21)18-15-19-20-16(25-15)24-7-9-3-1-2-4-9/h5-6,9H,1-4,7-8H2,(H,18,19,21)

Standard InChI Key:  XALPDHZZQDDISW-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   -2.1099    0.1096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3131   -0.1039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7297    0.4795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0995   -0.9006    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3027   -1.1141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2805   -0.5307    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.0257   -0.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8963   -1.7173    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -1.8414    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7401   -0.5098    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.4546   -0.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1689   -0.5098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1688    0.3149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9726    0.5650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4433   -0.0881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9516   -0.7555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6934   -0.4735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4875   -0.2598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7010    0.5370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1218    1.1185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3243    0.9097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4799   -1.2702    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.4433    0.9252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3161    1.7163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5008    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  6  5  1  0
  6  7  1  0
  7  8  2  0
  9  8  1  0
  5  9  2  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
 13 12  1  0
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 14 15  1  0
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 12 16  1  0
 17  1  2  0
 18 17  1  0
 19 18  2  0
 20 19  1  0
 21 20  2  0
  1 21  1  0
 17 22  1  0
 19 23  1  0
 23 24  1  0
 25 24  1  0
 20 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5289614

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 397.91

Molecular Weight (Monoisotopic): 397.0322

AlogP: 4.45

#Rotatable Bonds: 5

Polar Surface Area: 73.34

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.21

CX Basic pKa: ┄

CX LogP: 4.63

CX LogD: 4.26

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.59

Np Likeness Score: -1.92

References

1. Dodd CJ, Chronister KS, Rathnayake U, Parr LC, Li K, Chang S, Mi D, Days EL, Bauer JA, Cho HP, Boutaud O, Denton JS, Lindsley CW, Han C..  (2023)  Synthesis and SAR of a novel Kir6.2/SUR1 channel opener scaffold identified by HTS.,  87  [PMID:36966977] [10.1016/j.bmcl.2023.129256]

Source

Source(1):

• Scientific Literature