chloro-armeniaspirol

ID: ALA5271868

Max Phase: Preclinical

Molecular Formula: C18H20Cl3NO3

Molecular Weight: 404.72

Names and Identifiers

Canonical SMILES:  CCCCCCc1c(OC)c(Cl)cc2c1OC1(C2)NC(=O)C(Cl)=C1Cl

Standard InChI:  InChI=1S/C18H20Cl3NO3/c1-3-4-5-6-7-11-14-10(8-12(19)15(11)24-2)9-18(25-14)16(21)13(20)17(23)22-18/h8H,3-7,9H2,1-2H3,(H,22,23)

Standard InChI Key:  BXDFKEAQWQPFHR-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   -0.2256   -1.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9401   -1.0318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6520   -1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6520   -2.2689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9420   -2.6806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2256   -2.2726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5818   -1.1929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0544   -1.8492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5605   -2.5194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4671   -1.1346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2798   -1.3524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3694   -2.1214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6095   -2.4535    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8633   -0.7689    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.2535   -0.3375    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.9401   -0.2066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6547    0.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6547    1.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3694    1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3694    2.2689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0840    2.6815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3667   -1.0311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3667   -0.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3667   -2.6815    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.0840   -2.5341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  1  6  1  0
  6  5  2  0
  1  7  1  0
  7  8  1  0
  9  8  1  0
  6  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 13 12  1  0
  8 13  1  0
 11 14  1  0
 10 15  1  0
  2 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
  3 22  1  0
 22 23  1  0
  4 24  1  0
 12 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5271868

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 404.72

Molecular Weight (Monoisotopic): 403.0509

AlogP: 4.92

#Rotatable Bonds: 6

Polar Surface Area: 47.56

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.03

CX Basic pKa: ┄

CX LogP: 5.40

CX LogD: 5.32

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.68

Np Likeness Score: 0.48

References

1. Darnowski MG, Lanosky TD, Paquette AR, Boddy CN..  (2023)  Armeniaspirol analogues disrupt the electrical potential (ΔΨ) of the proton motive force.,  84  [PMID:36858079] [10.1016/j.bmcl.2023.129210]

Source

Source(1):

• Scientific Literature