(R)-4-[(Z)-4-(4-Hexyl-phenyl)-but-1-enyl]-2-((1R,2S)-2-methyl-cyclopropyl)-4,5-dihydro-thiazole

ID: ALA327770

PubChem CID: 44322989

Max Phase: Preclinical

Molecular Formula: C23H33NS

Molecular Weight: 355.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCc1ccc(CC/C=C\[C@@H]2CSC([C@@H]3C[C@@H]3C)=N2)cc1

Standard InChI:  InChI=1S/C23H33NS/c1-3-4-5-6-9-19-12-14-20(15-13-19)10-7-8-11-21-17-25-23(24-21)22-16-18(22)2/h8,11-15,18,21-22H,3-7,9-10,16-17H2,1-2H3/b11-8-/t18-,21+,22+/m0/s1

Standard InChI Key:  ZNJDFVRFRGYJEW-AUXHNBDHSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  1  0  0  0  0  0999 V2000
    9.5917   -4.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0417   -5.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4917   -6.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7667   -4.8375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8667   -5.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8417   -4.0542    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.5125   -4.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7250   -3.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1875   -3.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9000   -3.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1875   -5.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3042   -6.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5542   -5.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9167   -5.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3625   -5.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1292   -6.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5750   -5.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4542   -4.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6292   -4.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8625   -7.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0375   -7.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3292   -8.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7667   -7.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5917   -7.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5042   -8.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4167   -6.0792    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4417   -6.0875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  1  2  0
  5  2  1  0
  6  1  1  0
  7  4  1  0
  7  8  1  6
  9  6  1  0
 10  8  2  0
 11 19  1  0
 12 16  1  0
 13  5  1  0
 14 15  1  0
 15 11  2  0
 16 17  2  0
 17 11  1  0
 18 10  1  0
 19 18  1  0
 20 12  1  0
 21 20  1  0
 22 23  1  0
 23 24  1  0
 24 21  1  0
 25 22  1  0
  5 26  1  6
  2 27  1  6
  7  9  1  0
  3  5  1  0
 12 14  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA327770

   (R)-4-[(Z)-4-(4-Hexyl-phenyl)-but-1-enyl]-2-((1R,2S)-2-methyl-cyclopropyl)-4,5-dihydro-thiazole

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: 355.59

Molecular Weight (Monoisotopic): 355.2334

AlogP: 6.47

#Rotatable Bonds: 10

Polar Surface Area: 12.36

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 1

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 4.44

CX LogP: 7.49

CX LogD: 7.49

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.35

Np Likeness Score: 1.36

References

1. Nishikawa A, Shirai R, Koiso Y, Hashimoto Y, Iwasaki S.  (1997)  Design and synthesis of curacin a analogs with varied side chain structures,  7  (20): [10.1016/S0960-894X(97)10055-5]

Source

Source(1):

• Scientific Literature