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

ID: ALA4570019

PubChem CID: 155562373

Max Phase: Preclinical

Molecular Formula: C26H37Cl2N3O3

Molecular Weight: 437.58

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C26H35N3O3.2ClH/c1-18(2)29-17-23(26(31)32-4)22-9-8-21(24(22)25(29)30)16-28-12-10-27(11-13-28)15-20-7-5-6-19(3)14-20;;/h5-8,14,17-18,22,24H,9-13,15-16H2,1-4H3;2*1H/t22-,24-;;/m1../s1

Standard InChI Key:  PGXVLKAYSUFZHE-MACDPMPUSA-N

Molfile:  

     RDKit          2D

 36 37  0  0  0  0  0  0  0  0999 V2000
   37.8095  -29.9080    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   33.7396  -26.7733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0302  -28.0074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0302  -27.1861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2490  -26.9335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7686  -27.5987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2489  -28.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0261  -26.3647    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   33.0261  -28.8287    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   33.7396  -25.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4514  -25.5393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.0277  -25.5393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.1633  -25.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7300  -28.4159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7264  -29.2372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.4434  -28.0058    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.4464  -27.1845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9964  -29.0411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1929  -29.2151    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.9403  -29.9964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6420  -28.6037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8385  -28.7736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5860  -29.5549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.1369  -30.1663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7825  -29.7247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2316  -29.1174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4912  -28.3401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9411  -27.7290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1367  -27.8987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8853  -28.6848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4330  -29.2926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1499  -28.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1477  -29.2336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8588  -28.0097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1943  -26.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0142  -30.2464    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
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: 437.58

Molecular Weight (Monoisotopic): 437.2678

AlogP: 2.98

#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: 8.00

CX LogP: 2.89

CX LogD: 2.19

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.51

Np Likeness Score: -0.32

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