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

ID: ALA4582687

PubChem CID: 155558139

Max Phase: Preclinical

Molecular Formula: C23H30Cl2FN3O3

Molecular Weight: 413.49

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C23H28FN3O3.2ClH/c1-25-15-20(23(29)30-2)19-8-5-17(21(19)22(25)28)14-27-11-9-26(10-12-27)13-16-3-6-18(24)7-4-16;;/h3-7,15,19,21H,8-14H2,1-2H3;2*1H/t19-,21-;;/m1../s1

Standard InChI Key:  VDCPOFLWJOLJCJ-YYMFTFNESA-N

Molfile:  

     RDKit          2D

 34 35  0  0  0  0  0  0  0  0999 V2000
   24.3011  -11.2281    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   21.8945  -10.3841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1851  -11.6181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1851  -10.7969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4038  -10.5443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9234  -11.2095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4038  -11.8747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1809   -9.9755    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.1809  -12.4395    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.8944   -9.5628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6063   -9.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1826   -9.1501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3181   -9.5627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8849  -12.0267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8813  -12.8480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.5982  -11.6166    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.6012  -10.7953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1512  -12.6519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3477  -12.8259    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.0952  -13.6072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7968  -12.2144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9934  -12.3843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7408  -13.1656    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.2917  -13.7771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9373  -13.3355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3864  -12.7282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6461  -11.9509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0959  -11.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2915  -11.5094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0402  -12.2956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5879  -12.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3048  -12.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7438  -10.9030    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   22.5718  -13.8283    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
 29 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: 413.49

Molecular Weight (Monoisotopic): 413.2115

AlogP: 2.03

#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: 7.70

CX LogP: 1.75

CX LogD: 1.27

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.55

Np Likeness Score: -0.28

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