1-(14-((3-chloro-4,6-dihydroxy-2-methylbenzoyl)oxy)tetradecyl)-4-methylpyridin-1-ium bromide

ID: ALA4878802

PubChem CID: 164626064

Max Phase: Preclinical

Molecular Formula: C28H41BrClNO4

Molecular Weight: 491.09

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1cc[n+](CCCCCCCCCCCCCCOC(=O)c2c(O)cc(O)c(Cl)c2C)cc1.[Br-]

Standard InChI:  InChI=1S/C28H40ClNO4.BrH/c1-22-15-18-30(19-16-22)17-13-11-9-7-5-3-4-6-8-10-12-14-20-34-28(33)26-23(2)27(29)25(32)21-24(26)31;/h15-16,18-19,21H,3-14,17,20H2,1-2H3,(H-,31,32,33);1H

Standard InChI Key:  HFUOXBKSFZUART-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 35 35  0  0  0  0  0  0  0  0999 V2000
   17.0598   -4.6554    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.8694   -3.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8682   -4.4690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5830   -4.8819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2995   -4.4685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2967   -3.6380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5813   -3.2289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5788   -2.4038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0147   -4.8799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0095   -3.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7256   -3.6326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4384   -3.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0065   -2.3978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1545   -3.6272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8675   -3.2120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5834   -3.6219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2964   -3.2066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0124   -3.6164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7253   -3.2013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4413   -3.6111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1542   -3.1958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8702   -3.6057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5831   -3.1905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2991   -3.6003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0121   -3.1851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7280   -3.5949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4410   -3.1797    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1535   -4.8809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1564   -3.5916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8688   -3.1772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8662   -2.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1452   -1.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4356   -2.3585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5785   -1.9351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5828   -5.7069    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  7  8  1  0
  5  9  1  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
  3 28  1  0
 27 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 27  1  0
 31 34  1  0
  4 35  1  0
M  CHG  2   1  -1  27   1
M  END

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: 491.09

Molecular Weight (Monoisotopic): 490.2719

AlogP: 7.19

#Rotatable Bonds: 16

Polar Surface Area: 70.64

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.21

CX Basic pKa: ┄

CX LogP: 5.31

CX LogD: 4.92

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.15

Np Likeness Score: 0.20

References

1. Cueto-Díaz EJ, Ebiloma GU, Alfayez IA, Ungogo MA, Lemgruber L, González-García MC, Giron MD, Salto R, Fueyo-González FJ, Shiba T, González-Vera JA, Ruedas Rama MJ, Orte A, de Koning HP, Dardonville C..  (2021)  Synthesis, biological, and photophysical studies of molecular rotor-based fluorescent inhibitors of the trypanosome alternative oxidase.,  220  [PMID:33940464] [10.1016/j.ejmech.2021.113470]

Source

Source(1):

• Scientific Literature