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

ID: ALA4292398

PubChem CID: 145987873

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(Cl)c(C)c1C=O

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

Standard InChI Key:  VFTLBQKNCYOYPS-MDWZMJQESA-N

Molfile:  

     RDKit          2D

 22 22  0  0  0  0  0  0  0  0999 V2000
   10.7442  -14.1319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4449  -13.7108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4254  -12.8900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1280  -12.4653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8466  -12.8594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8625  -13.6782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1635  -14.1049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7638  -14.9528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7068  -12.4959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5456  -12.4326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1814  -14.9201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9035  -15.3162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6006  -14.8931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3191  -15.2872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0218  -14.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7404  -15.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4394  -14.8298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1580  -15.2239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8606  -14.7992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1775  -16.0448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3407  -16.1044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1085  -11.6444    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
  5 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
  7 11  1  0
  4 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4292398

   ---

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: ACID

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 5.95

CX Basic pKa: ┄

CX LogP: 5.36

CX LogD: 3.98

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.55

Np Likeness Score: 1.68

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