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

ID: ALA4875252

PubChem CID: 164627646

Max Phase: Preclinical

Molecular Formula: C26H26N2O2

Molecular Weight: 398.51

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C/C=C1\[C@H]2C=C(C)C[C@]1(Nc1ccc3cc(OC)ccc3c1)c1ccc(=O)[nH]c1C2

Standard InChI:  InChI=1S/C26H26N2O2/c1-4-22-19-11-16(2)15-26(22,23-9-10-25(29)27-24(23)14-19)28-20-7-5-18-13-21(30-3)8-6-17(18)12-20/h4-13,19,28H,14-15H2,1-3H3,(H,27,29)/b22-4+/t19-,26+/m0/s1

Standard InChI Key:  VAZOKHMFZPAYCS-SQYFZTEWSA-N

Molfile:  

 
     RDKit          2D

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   19.5628   -8.9618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   18.2203   -8.6062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4409   -7.8619    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.1942   -9.4719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1702   -7.6193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1864   -8.5895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0724   -8.3762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5758   -8.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9898   -7.4312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9470   -9.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0568   -9.6935    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.6767  -10.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8544   -8.0752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3996   -6.7077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8403  -10.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3840   -8.6021    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.7718  -10.1075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7681  -10.9350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1977  -10.1059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4829   -9.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1994  -10.9365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4822  -11.3464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4796  -12.1706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1935  -12.5858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9114  -12.1709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9104  -11.3481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6288  -12.5843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6295  -13.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 11  1  1  0
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  1 14  1  1
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  5 19  1  6
  5  8  1  0
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 28 30  1  0
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4875252

   ---

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: 398.51

Molecular Weight (Monoisotopic): 398.1994

AlogP: 5.31

#Rotatable Bonds: 3

Polar Surface Area: 54.12

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.06

CX Basic pKa: 3.41

CX LogP: 3.52

CX LogD: 3.52

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.59

Np Likeness Score: 0.72

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