2,2-dimethyl-2'-methylsulfanyl-6-nitrospiro[3,4-dihydro-2H-chromene-4,4'-(4',5'-dihydro-3'H-imidazole)]-5'-one

ID: ALA35834

PubChem CID: 10448739

Max Phase: Preclinical

Molecular Formula: C14H15N3O4S

Molecular Weight: 321.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CSC1=NC(=O)C2(CC(C)(C)Oc3ccc([N+](=O)[O-])cc32)N1

Standard InChI:  InChI=1S/C14H15N3O4S/c1-13(2)7-14(11(18)15-12(16-14)22-3)9-6-8(17(19)20)4-5-10(9)21-13/h4-6H,7H2,1-3H3,(H,15,16,18)

Standard InChI Key:  AHMYTNCGRFLEGX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   -1.7083   -5.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4208   -4.3750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2250   -4.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2333   -5.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0208   -4.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2000   -4.9542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7875   -5.3125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2333   -6.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7083   -6.5125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7500   -5.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1875   -5.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2708   -5.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1875   -6.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7875   -4.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3083   -5.6125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6583   -5.1292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7500   -6.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2708   -6.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3708   -3.8917    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7708   -6.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6708   -5.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1333   -3.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  1  1  0
  4  1  1  0
  5  6  1  0
  6  1  1  0
  7 12  1  0
  8  4  1  0
  9 13  1  0
 10  4  2  0
 11  1  1  0
 12 10  1  0
 13 11  1  0
 14  7  1  0
 15  7  2  0
 16  3  2  0
 17  8  2  0
 18 12  2  0
 19  5  1  0
 20 13  1  0
 21 13  1  0
 22 19  1  0
  5  2  2  0
  9  8  1  0
 18 17  1  0
M  CHG  2   7   1  14  -1
M  END

Alternative Forms

1. Parent:

   

   ALA35834

   2',2'-dimethyl-2-methylsulfanyl-6'-nitrospiro[1H-imidazole-4,4'-3H-chromene]-5-one

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 321.36

Molecular Weight (Monoisotopic): 321.0783

AlogP: 2.20

#Rotatable Bonds: 1

Polar Surface Area: 93.83

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.31

CX LogD: 2.31

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.63

Np Likeness Score: -0.40

References

1. Gadwood RC, Kamdar BV, Dubray LA, Wolfe ML, Smith MP, Watt W, Mizsak SA, Groppi VE..  (1993)  Synthesis and biological activity of spirocyclic benzopyran imidazolone potassium channel openers.,  36  (10): [PMID:8496916] [10.1021/jm00062a022]

Source

Source(1):

• Scientific Literature