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

ID: ALA4568939

PubChem CID: 155550830

Max Phase: Preclinical

Molecular Formula: C23H31Cl2N3O3

Molecular Weight: 395.50

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC(=O)C1=CN(C)C(=O)[C@@H]2C(CN3CCN(Cc4ccccc4)CC3)=CC[C@H]12.Cl.Cl

Standard InChI:  InChI=1S/C23H29N3O3.2ClH/c1-24-16-20(23(28)29-2)19-9-8-18(21(19)22(24)27)15-26-12-10-25(11-13-26)14-17-6-4-3-5-7-17;;/h3-8,16,19,21H,9-15H2,1-2H3;2*1H/t19-,21-;;/m1../s1

Standard InChI Key:  YITWLVNYNAOWDZ-YYMFTFNESA-N

Molfile:  

     RDKit          2D

 33 34  0  0  0  0  0  0  0  0999 V2000
   10.9124   -2.5073    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.4438   -2.3690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7344   -3.6031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7345   -2.7818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9532   -2.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4728   -3.1944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9531   -3.8596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7303   -1.9604    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7303   -4.4244    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4438   -1.5477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1556   -1.1350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7320   -1.1350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8675   -1.5477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4342   -4.0116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4306   -4.8329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1476   -3.6015    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1506   -2.7802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7006   -4.6368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8971   -4.8108    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6446   -5.5921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3462   -4.1994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5427   -4.3693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2902   -5.1506    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8411   -5.7620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4867   -5.3204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9358   -4.7131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1955   -3.9358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6453   -3.3247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8409   -3.4944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5895   -4.2805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1372   -4.8883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8542   -4.0121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8060   -4.9504    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
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: 395.50

Molecular Weight (Monoisotopic): 395.2209

AlogP: 1.90

#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: 7.97

CX LogP: 1.61

CX LogD: 0.93

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.56

Np Likeness Score: -0.03

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