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

ID: ALA4580013

PubChem CID: 155565539

Max Phase: Preclinical

Molecular Formula: C26H37Cl2N3O4

Molecular Weight: 453.58

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C26H35N3O4.2ClH/c1-18(2)29-17-23(26(31)33-4)22-9-8-20(24(22)25(29)30)16-28-12-10-27(11-13-28)15-19-6-5-7-21(14-19)32-3;;/h5-8,14,17-18,22,24H,9-13,15-16H2,1-4H3;2*1H/t22-,24-;;/m1../s1

Standard InChI Key:  FBKREVAMKMSKIL-MACDPMPUSA-N

Molfile:  

     RDKit          2D

 37 38  0  0  0  0  0  0  0  0999 V2000
   12.6128   -4.7360    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.2858   -2.1255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5764   -3.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5764   -2.5383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7951   -2.2857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3147   -2.9509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7951   -3.6161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5723   -1.7169    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5723   -4.1809    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2858   -1.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9976   -0.8915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5739   -0.8915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7094   -1.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2762   -3.7681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2726   -4.5894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9895   -3.3580    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9926   -2.5367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5425   -4.3933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7391   -4.5673    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4865   -5.3486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1881   -3.9559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3847   -4.1257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1321   -4.9071    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6830   -5.5185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3287   -5.0769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7777   -4.4696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0374   -3.6923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4873   -3.0812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6828   -3.2509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4315   -4.0370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9792   -4.6448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6961   -3.7686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6938   -4.5858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4049   -3.3619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7404   -2.3043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5399   -2.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2355   -5.9411    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
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: 453.58

Molecular Weight (Monoisotopic): 453.2628

AlogP: 2.68

#Rotatable Bonds: 7

Polar Surface Area: 62.32

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.77

CX LogP: 2.22

CX LogD: 1.70

Aromatic Rings: 1

Heavy Atoms: 33

QED Weighted: 0.47

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