3-((5aR,8R,9aR)-5,5,8-trimethyl-2-oxo-5a,6,7,8,9,9a-hexahydro-2H-isothiochromeno[3,4-d]thiazol-3(5H)-yl)propanenitrile

ID: ALA4777463

PubChem CID: 35581508

Max Phase: Preclinical

Molecular Formula: C16H22N2OS2

Molecular Weight: 322.50

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@@H]1CC[C@@H]2[C@@H](C1)c1sc(=O)n(CCC#N)c1SC2(C)C

Standard InChI:  InChI=1S/C16H22N2OS2/c1-10-5-6-12-11(9-10)13-14(21-16(12,2)3)18(8-4-7-17)15(19)20-13/h10-12H,4-6,8-9H2,1-3H3/t10-,11-,12-/m1/s1

Standard InChI Key:  VNDRADGYPQTACC-IJLUTSLNSA-N

Molfile:  

 
     RDKit          2D

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   40.5275  -14.0144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3561  -14.0185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9433  -13.2984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.0675  -13.5980    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   42.0675  -15.2551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3561  -14.8471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.6467  -15.2569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.6468  -16.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3625  -16.4928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.0739  -16.0772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.7831  -14.0185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.7877  -14.8435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.5739  -15.0929    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   44.0569  -14.4219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.5666  -13.7564    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.6358  -14.4307    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   41.3641  -17.3214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.7800  -15.6714    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   44.8825  -14.4182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   43.8212  -12.9669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.6266  -12.7910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.8770  -12.0057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.1241  -11.2224    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  2  6  1  0
  2  4  1  0
  5 12  1  0
 11  4  1  0
  5  6  1  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 11  1  0
  6 16  1  6
  9 17  1  6
  5 18  1  1
 14 19  2  0
 15 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA4777463

   3-[(5aR,8R,9aR)-5,5,8-trimethyl-2-oxo-5a,6,7,8,9,9a-hexahydroisothiochromeno[3,4-d][1,3]thiazol-3-yl]propanenitrile

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: 322.50

Molecular Weight (Monoisotopic): 322.1174

AlogP: 4.23

#Rotatable Bonds: 2

Polar Surface Area: 45.79

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.56

CX LogD: 3.56

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.82

Np Likeness Score: -0.04

References

1. Schadich E,Kryshchyshyn-Dylevych A,Holota S,Polishchuk P,Džubak P,Gurska S,Hajduch M,Lesyk R.  (2020)  Assessing different thiazolidine and thiazole based compounds as antileishmanial scaffolds.,  30  (23.0): [PMID:33091607] [10.1016/j.bmcl.2020.127616]

Source

Source(1):

• Scientific Literature