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

ID: ALA4483802

PubChem CID: 155540651

Max Phase: Preclinical

Molecular Formula: C25H34Cl2FN3O3

Molecular Weight: 441.55

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC(=O)C1=CN(C(C)C)C(=O)[C@@H]2C(CN3CCN(Cc4ccc(F)cc4)CC3)=CC[C@H]12.Cl.Cl

Standard InChI:  InChI=1S/C25H32FN3O3.2ClH/c1-17(2)29-16-22(25(31)32-3)21-9-6-19(23(21)24(29)30)15-28-12-10-27(11-13-28)14-18-4-7-20(26)8-5-18;;/h4-8,16-17,21,23H,9-15H2,1-3H3;2*1H/t21-,23-;;/m1../s1

Standard InChI Key:  CEQRCAFGYBAKGK-GBUPLUEPSA-N

Molfile:  

     RDKit          2D

 36 37  0  0  0  0  0  0  0  0999 V2000
   25.6301   -4.4553    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   22.2123   -2.4474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5029   -3.6815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5029   -2.8602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7216   -2.6076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2412   -3.2729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7216   -3.9380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4987   -2.0389    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.4987   -4.5028    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   22.2122   -1.6261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9241   -1.2134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5004   -1.2134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.6359   -1.6261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2027   -4.0900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1991   -4.9114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9160   -3.6799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.9190   -2.8586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4690   -4.7152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6655   -4.8892    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.4130   -5.6705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1146   -4.2778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3112   -4.4477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0586   -5.2290    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.6095   -5.8404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2551   -5.3989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7042   -4.7916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9639   -4.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4137   -3.4032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6093   -3.5728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3580   -4.3589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9057   -4.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6226   -4.0905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6203   -4.9077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3314   -3.6839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0616   -2.9663    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   22.5718   -6.1558    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
 29 35  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: 441.55

Molecular Weight (Monoisotopic): 441.2428

AlogP: 2.81

#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: 7.70

CX LogP: 2.52

CX LogD: 2.05

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.50

Np Likeness Score: -0.35

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