(5R,9R)-5-((2,3-dihydrobenzo[b][1,4]dioxin-6-yl)amino)-11-ethylidene-7-methyl-5,6,9,10-tetrahydro-5,9-methanocycloocta[b]pyridin-2(1H)-one

ID: ALA4873701

PubChem CID: 164621198

Max Phase: Preclinical

Molecular Formula: C23H24N2O3

Molecular Weight: 376.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C/C=C1\[C@H]2C=C(C)C[C@]1(Nc1ccc3c(c1)OCCO3)c1ccc(=O)[nH]c1C2

Standard InChI:  InChI=1S/C23H24N2O3/c1-3-17-15-10-14(2)13-23(17,18-5-7-22(26)24-19(18)11-15)25-16-4-6-20-21(12-16)28-9-8-27-20/h3-7,10,12,15,25H,8-9,11,13H2,1-2H3,(H,24,26)/b17-3+/t15-,23+/m0/s1

Standard InChI Key:  QMEKBENGUAMHQU-FJLRBPAYSA-N

Molfile:  

 
     RDKit          2D

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   25.9875   -2.8754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9028   -2.8671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0324   -2.0688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4358   -3.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5612   -2.5119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7805   -1.7679    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.5339   -3.3770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5111   -1.5254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5267   -2.4951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4116   -2.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9164   -1.9183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3302   -1.3374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2862   -3.0844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3971   -3.5984    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.0179   -4.0415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1931   -1.9810    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.7398   -0.6144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1820   -4.0415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7254   -2.5076    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   27.1118   -4.0122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8224   -3.6006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8218   -5.2528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1105   -4.8372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5368   -4.0106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5368   -4.8443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2548   -5.2589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.9773   -4.8443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9774   -4.0107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2548   -3.5915    0.0000 O   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 23  2  0
 22 25  2  0
 24 21  2  0
 21 20  1  0
 22 23  1  0
 24 25  1  0
 24 29  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4873701

   ---

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: 376.46

Molecular Weight (Monoisotopic): 376.1787

AlogP: 3.92

#Rotatable Bonds: 2

Polar Surface Area: 63.35

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.06

CX Basic pKa: 4.29

CX LogP: 2.20

CX LogD: 2.20

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.78

Np Likeness Score: 0.64

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