3-Chloro-4-{[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-6-hydroxy-2-methylbenzaldehyde

ID: ALA4292788

PubChem CID: 145986504

Max Phase: Preclinical

Molecular Formula: C18H23ClO3

Molecular Weight: 322.83

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)=CCC/C(C)=C/COc1cc(O)c(C=O)c(C)c1Cl

Standard InChI:  InChI=1S/C18H23ClO3/c1-12(2)6-5-7-13(3)8-9-22-17-10-16(21)15(11-20)14(4)18(17)19/h6,8,10-11,21H,5,7,9H2,1-4H3/b13-8+

Standard InChI Key:  SXUMPIBOPLKXSS-MDWZMJQESA-N

Molfile:  

     RDKit          2D

 22 22  0  0  0  0  0  0  0  0999 V2000
   12.2484   -7.4834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5381   -7.8911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5381   -8.7107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8278   -9.1225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1175   -8.7107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1175   -7.8911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8278   -7.4834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9587   -7.8911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2484   -9.1225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8278   -6.6639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4113   -9.1225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7010   -8.7107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9907   -9.1225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2804   -8.7107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5701   -9.1225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8599   -8.7107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1496   -9.1225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4434   -8.7107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7331   -9.1225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4434   -7.8911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2804   -7.8911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8278   -9.9420    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  2  7  2  0
  1  8  2  0
  3  9  1  0
  7 10  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 14 21  1  0
 11 12  1  0
  5 11  1  0
  4 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4292788

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 322.83

Molecular Weight (Monoisotopic): 322.1336

AlogP: 5.24

#Rotatable Bonds: 7

Polar Surface Area: 46.53

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.99

CX Basic pKa: ┄

CX LogP: 6.01

CX LogD: 5.91

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.55

Np Likeness Score: 1.72

References

1. West RA, O'Doherty OG, Askwith T, Atack J, Beswick P, Laverick J, Paradowski M, Pennicott LE, Rao SPS, Williams G, Ward SE..  (2017)  African trypanosomiasis: Synthesis & SAR enabling novel drug discovery of ubiquinol mimics for trypanosome alternative oxidase.,  141  [PMID:29107420] [10.1016/j.ejmech.2017.09.067]

Source

Source(1):

• Scientific Literature