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

ID: ALA4466286

PubChem CID: 155531614

Max Phase: Preclinical

Molecular Formula: C23H30Cl2N4O5

Molecular Weight: 440.50

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C23H28N4O5.2ClH/c1-24-15-20(23(29)32-2)19-8-5-17(21(19)22(24)28)14-26-11-9-25(10-12-26)13-16-3-6-18(7-4-16)27(30)31;;/h3-7,15,19,21H,8-14H2,1-2H3;2*1H/t19-,21-;;/m1../s1

Standard InChI Key:  JKTGQWMGGXOIRK-YYMFTFNESA-N

Molfile:  

     RDKit          2D

 36 37  0  0  0  0  0  0  0  0999 V2000
    9.9549  -22.0208    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.4727  -18.7376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7633  -19.9717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7634  -19.1504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9821  -18.8978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5017  -19.5630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9820  -20.2282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7592  -18.3290    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7592  -20.7930    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4727  -17.9163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1845  -17.5036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7609  -17.5036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8964  -17.9163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4631  -20.3802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4595  -21.2015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1765  -19.9701    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1795  -19.1488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7295  -21.0054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9260  -21.1794    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6734  -21.9607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3751  -20.5680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5716  -20.7378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3191  -21.5192    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8700  -22.1306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5156  -21.6890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9647  -21.0817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2243  -20.3044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6742  -19.6933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8698  -19.8630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6184  -20.6491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1661  -21.2569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8830  -20.3807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3243  -19.2526    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5253  -19.4238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5757  -18.4751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8835  -19.4537    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
 33 34  2  0
 33 35  1  0
 29 33  1  0
M  CHG  2  33   1  35  -1
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: 440.50

Molecular Weight (Monoisotopic): 440.2060

AlogP: 1.80

#Rotatable Bonds: 6

Polar Surface Area: 96.23

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.60

CX LogP: 1.55

CX LogD: 1.14

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.29

Np Likeness Score: -0.34

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