2-(2-Methyl-cyclopropyl)-4-(8-methyl-nona-1,5,7-trienyl)-4,5-dihydro-thiazole

ID: ALA88531

PubChem CID: 44323027

Max Phase: Preclinical

Molecular Formula: C17H25NS

Molecular Weight: 275.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)=C/C=C/CC/C=C\[C@@H]1CSC([C@@H]2C[C@@H]2C)=N1

Standard InChI:  InChI=1S/C17H25NS/c1-13(2)9-7-5-4-6-8-10-15-12-19-17(18-15)16-11-14(16)3/h5,7-10,14-16H,4,6,11-12H2,1-3H3/b7-5+,10-8-/t14-,15+,16+/m0/s1

Standard InChI Key:  ABDZABIBSBAXPA-XHMZZEABSA-N

Molfile:  

     RDKit          2D

 21 22  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
    3.9167   -5.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3625   -5.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1000   -5.7542    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
    5.1875   -5.1250    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
   11.5542   -5.0292    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
    6.4542   -4.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6542   -6.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7167   -5.0167    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
  8  9  1  0
  9 13  2  0
 10  8  2  0
  7 11  1  6
 12  6  1  0
 13 16  1  0
 14 11  2  0
 15  5  1  0
 16 17  1  0
 17 14  1  0
 18 10  1  0
 19 10  1  0
  5 20  1  6
  2 21  1  6
  7 12  1  0
  3  5  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA88531

   (R)-2-((1R,2S)-2-Methyl-cyclopropyl)-4-((1Z,5E)-8-methyl-nona-1,5,7-trienyl)-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: 275.46

Molecular Weight (Monoisotopic): 275.1708

AlogP: 5.02

#Rotatable Bonds: 6

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: 4.35

CX LogP: 4.91

CX LogD: 4.91

Aromatic Rings: ┄

Heavy Atoms: 19

QED Weighted: 0.38

Np Likeness Score: 2.45

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