(4aS,7aS)-methyl 7-((4-(3-trifluoromethylbenzyl)piperazin-1-yl)methyl)-2-isopropyl-1-oxo-2,4a,5,7a-tetrahydro-1H-cyclopenta[c]pyridine-4-carboxylate dihydrochloride

ID: ALA4533886

PubChem CID: 155546903

Max Phase: Preclinical

Molecular Formula: C26H34Cl2F3N3O3

Molecular Weight: 491.55

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC(=O)C1=CN(C(C)C)C(=O)[C@@H]2C(CN3CCN(Cc4cccc(C(F)(F)F)c4)CC3)=CC[C@H]12.Cl.Cl

Standard InChI:  InChI=1S/C26H32F3N3O3.2ClH/c1-17(2)32-16-22(25(34)35-3)21-8-7-19(23(21)24(32)33)15-31-11-9-30(10-12-31)14-18-5-4-6-20(13-18)26(27,28)29;;/h4-7,13,16-17,21,23H,8-12,14-15H2,1-3H3;2*1H/t21-,23-;;/m1../s1

Standard InChI Key:  GFCYBYFYEFKJSH-GBUPLUEPSA-N

Molfile:  

     RDKit          2D

 39 40  0  0  0  0  0  0  0  0999 V2000
   38.3997  -10.6709    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   34.8705  -10.3759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1611  -11.6099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1611  -10.7886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3798  -10.5360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8994  -11.2013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3798  -11.8664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1569   -9.9673    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   34.1569  -12.4312    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   34.8705   -9.5545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5823   -9.1418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.1586   -9.1418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.2941   -9.5545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8609  -12.0184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8573  -12.8398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.5742  -11.6084    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.5773  -10.7870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1272  -12.6436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3237  -12.8176    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.0712  -13.5989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7728  -12.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9694  -12.3761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7168  -13.1574    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.2677  -13.7688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9134  -13.3273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3624  -12.7200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6221  -11.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0719  -11.3316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2675  -11.5012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0162  -12.2873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5639  -12.8951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2808  -12.0189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2785  -12.8361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9896  -11.6123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3251  -10.5546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1246  -10.3854    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   28.7788   -9.9468    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   29.5344   -9.7609    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   35.5850  -14.3813    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  4  2  1  0
  3 14  1  0
 17  2  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  3  1  0
  4  8  1  1
  3  9  1  1
  2 10  1  0
 10 11  1  0
 10 12  2  0
 11 13  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
  7 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 20 24  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 26  1  0
 16 32  1  0
 32 33  1  0
 32 34  1  0
 28 35  1  0
 35 36  1  0
 35 37  1  0
 35 38  1  0
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 491.55

Molecular Weight (Monoisotopic): 491.2396

AlogP: 3.69

#Rotatable Bonds: 6

Polar Surface Area: 53.09

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.63

CX LogP: 3.26

CX LogD: 2.83

Aromatic Rings: 1

Heavy Atoms: 35

QED Weighted: 0.45

Np Likeness Score: -0.52

References

1. Zhang Z, Wang Y, Zhang Y, Li J, Huang W, Wang L..  (2019)  The synthesis and biological evaluation of novel gardenamide A derivatives as multifunctional neuroprotective agents.,  10  (7): [PMID:31391892] [10.1039/C9MD00211A]

Source

Source(1):

• Scientific Literature