(5R,9R)-11-ethylidene-7-methyl-5-(naphthalen-1-ylamino)-5,6,9,10-tetrahydro-5,9-methanocycloocta[b]pyridin-2(1H)-one

ID: ALA4867752

PubChem CID: 164621833

Max Phase: Preclinical

Molecular Formula: C25H24N2O

Molecular Weight: 368.48

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C/C=C1\[C@H]2C=C(C)C[C@]1(Nc1cccc3ccccc13)c1ccc(=O)[nH]c1C2

Standard InChI:  InChI=1S/C25H24N2O/c1-3-20-18-13-16(2)15-25(20,21-11-12-24(28)26-23(21)14-18)27-22-10-6-8-17-7-4-5-9-19(17)22/h3-13,18,27H,14-15H2,1-2H3,(H,26,28)/b20-3+/t18-,25+/m0/s1

Standard InChI Key:  GNUNRYDAAXJBTP-USNQOEAHSA-N

Molfile:  

 
     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
   19.7964   -2.6665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7131   -2.6582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8430   -1.8587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2439   -3.1103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3694   -2.3024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5922   -1.5572    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.3452   -3.1689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3192   -1.3144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3364   -2.2857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2244   -2.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7252   -1.7079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1397   -1.1261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0988   -2.8759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2066   -3.3908    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.8252   -3.8345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0071   -1.7707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5499   -0.4019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9880   -3.8345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5321   -2.2982    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.9225   -3.8053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3515   -4.6351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3499   -3.8036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6343   -3.3930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6337   -5.0478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9213   -4.6315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2066   -5.0403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2032   -5.8652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9204   -6.2796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6321   -5.8685    0.0000 C   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 25  2  0
 24 21  2  0
 21 22  1  0
 22 23  2  0
 23 20  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4867752

   ---

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: 368.48

Molecular Weight (Monoisotopic): 368.1889

AlogP: 5.30

#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: 3.20

CX LogP: 3.68

CX LogD: 3.68

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.60

Np Likeness Score: 0.74

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