1-Adamantyl-3-[(4-acetamidophenyl)sulfonyl]thiourea

ID: ALA3247967

PubChem CID: 3007731

Max Phase: Preclinical

Molecular Formula: C19H25N3O3S2

Molecular Weight: 407.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)Nc1ccc(S(=O)(=O)NC(=S)NC23CC4CC(CC(C4)C2)C3)cc1

Standard InChI:  InChI=1S/C19H25N3O3S2/c1-12(23)20-16-2-4-17(5-3-16)27(24,25)22-18(26)21-19-9-13-6-14(10-19)8-15(7-13)11-19/h2-5,13-15H,6-11H2,1H3,(H,20,23)(H2,21,22,26)

Standard InChI Key:  QNPGFPXVZQBELO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   15.8610   -8.7135    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.2737   -7.9991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4486   -7.9989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9058   -9.3212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5471   -8.6376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7102   -9.0962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2584   -8.9002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4630   -9.3989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0064   -8.7147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7076   -8.2478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2642   -7.5857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5426   -7.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0121   -7.8957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7173   -9.1254    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4319   -8.7131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1464   -9.1258    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4322   -7.8881    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.5754   -9.1261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5729   -9.9516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2864  -10.3642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0020   -9.9518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9996   -9.1225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2854   -8.7136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7170  -10.3635    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.4310   -9.9503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1460  -10.3620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4302   -9.1252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  1  3  2  0
  4  5  1  0
  4  6  1  0
  5  7  1  0
  6  8  1  0
  7  9  1  0
  8  9  1  0
 10 11  1  0
  6 10  1  0
  5 12  1  0
  9 13  1  0
 13 11  1  0
 11 12  1  0
  9 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 16  1  1  0
  1 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 21 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3247967

   N-[4-(1-adamantylcarbamothioylsulfamoyl)phenyl]acetamide

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: 407.56

Molecular Weight (Monoisotopic): 407.1337

AlogP: 2.77

#Rotatable Bonds: 4

Polar Surface Area: 87.30

Molecular Species: ACID

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.05

CX Basic pKa: ┄

CX LogP: 2.68

CX LogD: 1.86

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.67

Np Likeness Score: -1.30

References

1. Tilley JW, Levitan P, Kramer MJ..  (1979)  Adamantylthiourea derivatives as antiviral agents.,  22  (8): [PMID:490532] [10.1021/jm00194a025]

Source

Source(1):

• Scientific Literature