5-[(6-Chloro-1,2,3,4-tetrahydroacridin-9-yl)amino]-N-(9-fluoro-7H-5,6,8,9,10,11-hexahydro-5,9:7,11-dimethanobenzo[9]annulen-7-yl)pentanamide

ID: ALA4462369

PubChem CID: 155529070

Max Phase: Preclinical

Molecular Formula: C33H37ClFN3O

Molecular Weight: 546.13

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(CCCCNc1c2c(nc3cc(Cl)ccc13)CCCC2)NC12CC3CC(F)(CC(C1)c1ccccc13)C2

Standard InChI:  InChI=1S/C33H37ClFN3O/c34-23-12-13-27-29(15-23)37-28-10-4-3-9-26(28)31(27)36-14-6-5-11-30(39)38-33-18-21-16-32(35,20-33)17-22(19-33)25-8-2-1-7-24(21)25/h1-2,7-8,12-13,15,21-22H,3-6,9-11,14,16-20H2,(H,36,37)(H,38,39)

Standard InChI Key:  QCLKADUVPRHWRU-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   19.2055   -8.9214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7940   -8.9421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   17.7940   -9.7592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4874   -7.7080    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.9072   -8.5128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   19.9196  -10.1472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   15.6704  -10.1674    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
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   14.2067   -2.8813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6636   -2.8813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9331   -1.6927    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.6991   -3.9956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7115   -4.7922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2853   -3.9992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.9905   -3.5904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3686   -4.0282    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3676   -4.8454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0749   -5.2548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6594   -5.2531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0739   -6.0720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   17.7802   -7.2986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  6  1  0
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  5  2  2  0
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 27 32  2  0
 32 29  1  0
 19 33  1  0
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 34 36  2  0
 35 37  1  0
 37 38  1  0
 38 39  1  0
 39  7  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4462369

   ---

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: 546.13

Molecular Weight (Monoisotopic): 545.2609

AlogP: 7.77

#Rotatable Bonds: 7

Polar Surface Area: 54.02

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 8.09

CX LogP: 6.20

CX LogD: 5.45

Aromatic Rings: 3

Heavy Atoms: 39

QED Weighted: 0.30

Np Likeness Score: -0.74

References

1. Pérez-Areales FJ, Turcu AL, Barniol-Xicota M, Pont C, Pivetta D, Espargaró A, Bartolini M, De Simone A, Andrisano V, Pérez B, Sabate R, Sureda FX, Vázquez S, Muñoz-Torrero D..  (2019)  A novel class of multitarget anti-Alzheimer benzohomoadamantane‒chlorotacrine hybrids modulating cholinesterases and glutamate NMDA receptors.,  180  [PMID:31351393] [10.1016/j.ejmech.2019.07.051]

Source

Source(1):

• Scientific Literature