(5R,9R)-11-ethylidene-5-((4-methoxyphenyl)amino)-7-methyl-5,6,9,10-tetrahydro-5,9-methanocycloocta[b]pyridin-2(1H)-one

ID: ALA4872810

PubChem CID: 164621615

Max Phase: Preclinical

Molecular Formula: C22H24N2O2

Molecular Weight: 348.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C/C=C1\[C@H]2C=C(C)C[C@]1(Nc1ccc(OC)cc1)c1ccc(=O)[nH]c1C2

Standard InChI:  InChI=1S/C22H24N2O2/c1-4-18-15-11-14(2)13-22(18,19-9-10-21(25)23-20(19)12-15)24-16-5-7-17(26-3)8-6-16/h4-11,15,24H,12-13H2,1-3H3,(H,23,25)/b18-4+/t15-,22+/m0/s1

Standard InChI Key:  YGBASQWMZQOOBL-IHHYUWNCSA-N

Molfile:  

 
     RDKit          2D

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   29.3974  -16.5382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3109  -16.5298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4401  -15.7331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8468  -16.9802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9719  -16.1752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1868  -15.4327    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.9407  -17.0386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9219  -15.1909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9354  -16.1586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8166  -15.9458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3264  -15.5829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7394  -15.0031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6915  -16.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8062  -17.2597    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.4297  -17.7019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5966  -15.6455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.1482  -14.2816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5955  -17.7019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1377  -16.1711    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   30.5194  -17.6727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5156  -18.4978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2280  -18.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9432  -18.4994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9416  -17.6710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2286  -17.2618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6585  -18.9123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.6586  -19.7382    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
 23 26  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4872810

   ---

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: 348.45

Molecular Weight (Monoisotopic): 348.1838

AlogP: 4.16

#Rotatable Bonds: 3

Polar Surface Area: 54.12

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: 4.71

CX LogP: 2.53

CX LogD: 2.53

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.82

Np Likeness Score: 0.87

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