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

ID: ALA4551804

PubChem CID: 155555758

Max Phase: Preclinical

Molecular Formula: C24H33Cl2N3O3

Molecular Weight: 409.53

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C24H31N3O3.2ClH/c1-17-5-4-6-18(13-17)14-26-9-11-27(12-10-26)15-19-7-8-20-21(24(29)30-3)16-25(2)23(28)22(19)20;;/h4-7,13,16,20,22H,8-12,14-15H2,1-3H3;2*1H/t20-,22-;;/m1../s1

Standard InChI Key:  KHCJZAVTUQAMFX-HRXPAQHTSA-N

Molfile:  

     RDKit          2D

 34 35  0  0  0  0  0  0  0  0999 V2000
   37.8426   -3.2502    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   34.6022   -2.7405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8928   -3.9745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8928   -3.1532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1116   -2.9006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6311   -3.5659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1115   -4.2311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8887   -2.3319    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   33.8887   -4.7958    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   34.6022   -1.9192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3140   -1.5064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.8903   -1.5065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.0259   -1.9191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5926   -4.3831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5890   -5.2044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.3060   -3.9730    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.3090   -3.1517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8589   -5.0082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0555   -5.1823    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.8029   -5.9636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5046   -4.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7011   -4.7407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4485   -5.5220    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.9995   -6.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6451   -5.6919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0942   -5.0846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3538   -4.3073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8037   -3.6962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9993   -3.8658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7479   -4.6520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2956   -5.2597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0125   -4.3835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0569   -2.9192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4092   -5.3840    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
 28 33  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: 409.53

Molecular Weight (Monoisotopic): 409.2365

AlogP: 2.20

#Rotatable Bonds: 5

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: 8.00

CX LogP: 2.12

CX LogD: 1.42

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.55

Np Likeness Score: -0.25

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