(5R,9R)-5-((3,5-bis(trifluoromethyl)phenyl)amino)-11-ethylidene-7-methyl-5,6,9,10-tetrahydro-5,9-methanocycloocta[b]pyridin-2(1H)-one

ID: ALA4878978

PubChem CID: 164628587

Max Phase: Preclinical

Molecular Formula: C23H20F6N2O

Molecular Weight: 454.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C/C=C1\[C@H]2C=C(C)C[C@]1(Nc1cc(C(F)(F)F)cc(C(F)(F)F)c1)c1ccc(=O)[nH]c1C2

Standard InChI:  InChI=1S/C23H20F6N2O/c1-3-17-13-6-12(2)11-21(17,18-4-5-20(32)30-19(18)7-13)31-16-9-14(22(24,25)26)8-15(10-16)23(27,28)29/h3-6,8-10,13,31H,7,11H2,1-2H3,(H,30,32)/b17-3+/t13-,21+/m0/s1

Standard InChI Key:  PMMKNWUZLASFDZ-QPUXKKDASA-N

Molfile:  

 
     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
   10.8716   -8.5988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7848   -8.5905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9141   -7.7940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3211   -9.0409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4462   -8.2361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6606   -7.4937    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4146   -9.0993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3962   -7.2519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4095   -8.2194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2903   -8.0067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8007   -7.6439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2135   -7.0642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1652   -8.8074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2803   -9.3203    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9041   -9.7623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0701   -7.7064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6222   -6.3428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0701   -9.7623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6122   -8.2318    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9933   -9.7332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9896  -10.5582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7018  -10.9709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4169  -10.5598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4153   -9.7315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7024   -9.3225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7004  -11.7966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9847  -12.2083    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.1068  -12.5063    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.4946  -11.5764    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.1293   -9.3170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8454   -9.7281    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.7114   -8.5988    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.5371   -8.5988    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  2  0
  4  1  1  0
  5  4  1  0
  6  3  1  0
  7  2  1  0
  8 12  2  0
  9  5  1  0
 10 13  1  0
 11  1  1  0
 12 11  1  0
 13  7  2  0
  1 14  1  1
 15  4  2  0
 16 10  2  0
 17 12  1  0
 18 15  1  0
  5 19  1  6
  5  8  1  0
  3  9  1  0
  6 10  1  0
 14 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 22 26  1  0
 26 27  1  0
 26 28  1  0
 26 29  1  0
 24 30  1  0
 30 31  1  0
 30 32  1  0
 30 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4878978

   ---

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: 454.41

Molecular Weight (Monoisotopic): 454.1480

AlogP: 6.19

#Rotatable Bonds: 2

Polar Surface Area: 44.89

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.06

CX Basic pKa: 2.68

CX LogP: 4.44

CX LogD: 4.44

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.42

Np Likeness Score: 0.46

References

1. Miao SX, Wan LX, He ZX, Zhou XL, Li X, Gao F..  (2021)  Pd-Catalyzed Direct Diversification of Natural Anti-Alzheimer's Disease Drug: Synthesis and Biological Evaluation of N-Aryl Huperzine A Analogues.,  84  (8.0): [PMID:34445873] [10.1021/acs.jnatprod.1c00600]

Source

Source(1):

• Scientific Literature