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

ID: ALA4866597

PubChem CID: 164623755

Max Phase: Preclinical

Molecular Formula: C21H23N3O

Molecular Weight: 333.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C/C=C1\[C@H]2C=C(C)C[C@]1(Nc1cccc(C)n1)c1ccc(=O)[nH]c1C2

Standard InChI:  InChI=1S/C21H23N3O/c1-4-16-15-10-13(2)12-21(16,24-19-7-5-6-14(3)22-19)17-8-9-20(25)23-18(17)11-15/h4-10,15H,11-12H2,1-3H3,(H,22,24)(H,23,25)/b16-4+/t15-,21+/m0/s1

Standard InChI Key:  ILYRKZQYABAXEP-MEKFFGMDSA-N

Molfile:  

 
     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   26.9991  -15.7415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9125  -15.7331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0418  -14.9364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4485  -16.1835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5736  -15.3786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7884  -14.6361    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.5423  -16.2419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5235  -14.3942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5371  -15.3619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4182  -15.1492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9281  -14.7863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3411  -14.2065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2931  -15.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4078  -16.4631    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.0313  -16.9052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1982  -14.8488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.7499  -13.4849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1972  -16.9052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7394  -15.3744    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   28.1211  -16.8760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1172  -17.7012    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.8297  -18.1140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5449  -17.7028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5432  -16.8744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8302  -16.4652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8283  -18.9399    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 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
M  END

Alternative Forms

1. Parent:

   

   ALA4866597

   ---

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: 333.44

Molecular Weight (Monoisotopic): 333.1841

AlogP: 3.85

#Rotatable Bonds: 2

Polar Surface Area: 57.78

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.06

CX Basic pKa: 7.25

CX LogP: 2.20

CX LogD: 1.97

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.82

Np Likeness Score: 0.62

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