4-[4-(3-Heptyl-phenyl)-but-1-enyl]-2-(2-methyl-cyclopropyl)-4,5-dihydro-thiazole

ID: ALA89124

PubChem CID: 44323009

Max Phase: Preclinical

Molecular Formula: C24H35NS

Molecular Weight: 369.62

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCc1cccc(CC/C=C\[C@@H]2CSC([C@@H]3C[C@@H]3C)=N2)c1

Standard InChI:  InChI=1S/C24H35NS/c1-3-4-5-6-7-11-20-13-10-14-21(17-20)12-8-9-15-22-18-26-24(25-22)23-16-19(23)2/h9-10,13-15,17,19,22-23H,3-8,11-12,16,18H2,1-2H3/b15-9-/t19-,22+,23+/m0/s1

Standard InChI Key:  JJFNYMYMBCMWBD-FQWYBILGSA-N

Molfile:  

     RDKit          2D

 28 30  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
    4.3625   -5.0875    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
    5.1875   -5.1250    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
    5.1292   -6.5542    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
    4.3042   -6.5250    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
    5.6292   -4.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0917   -5.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6500   -6.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1167   -7.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5625   -7.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8292   -6.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3875   -7.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7083   -7.7375    0.0000 C   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
   11.4167   -6.0792    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 13  2  0
 12  5  1  0
 13 19  1  0
 14 11  1  0
 15 18  2  0
 16 10  1  0
 17 15  1  0
 18 13  1  0
 19 16  1  0
 20 14  1  0
 21 20  1  0
 22 23  1  0
 23 25  1  0
 24 21  1  0
 25 24  1  0
 26 22  1  0
  2 27  1  6
  5 28  1  6
  7  9  1  0
  3  5  1  0
 17 14  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA89124

   (R)-4-[(Z)-4-(3-Heptyl-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: 369.62

Molecular Weight (Monoisotopic): 369.2490

AlogP: 6.86

#Rotatable Bonds: 11

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: 4.48

CX LogP: 7.93

CX LogD: 7.93

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.31

Np Likeness Score: 1.29

References

1. Wipf P, Reeves JT, Balachandran R, Day BW..  (2002)  Synthesis and biological evaluation of structurally highly modified analogues of the antimitotic natural product curacin A.,  45  (9): [PMID:11960501] [10.1021/jm0105171]

2. 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