2-Chloro-6-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-4-formyl-5-hydroxy-3-methylphenyl acetate

ID: ALA4283939

PubChem CID: 145991670

Max Phase: Preclinical

Molecular Formula: C20H25ClO4

Molecular Weight: 364.87

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)Oc1c(Cl)c(C)c(C=O)c(O)c1C/C=C(\C)CCC=C(C)C

Standard InChI:  InChI=1S/C20H25ClO4/c1-12(2)7-6-8-13(3)9-10-16-19(24)17(11-22)14(4)18(21)20(16)25-15(5)23/h7,9,11,24H,6,8,10H2,1-5H3/b13-9+

Standard InChI Key:  WJHYFHZXMCKNHI-UKTHLTGXSA-N

Molfile:  

     RDKit          2D

 25 25  0  0  0  0  0  0  0  0999 V2000
   13.5747  -10.3309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5747  -11.1565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2902  -11.5713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2902  -12.3968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5747  -12.8075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8592  -12.3968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8592  -11.5713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8592   -9.9202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5747  -13.6331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0057  -11.1565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0057  -12.8075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7170  -12.3968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4325  -12.8075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1480  -12.3968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8635  -12.8075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5790  -12.3968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2945  -12.8075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0101  -12.3968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2945  -13.6331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4325  -13.6331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1437  -12.8075    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   12.8549  -14.0486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8549  -14.8797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1352  -13.6331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1390  -11.1565    0.0000 C   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
  5  9  1  0
  3 10  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 13 20  1  0
  4 11  1  0
  6 21  1  0
  9 22  1  0
 22 23  1  0
 22 24  2  0
  7 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4283939

   ---

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: 364.87

Molecular Weight (Monoisotopic): 364.1441

AlogP: 5.33

#Rotatable Bonds: 7

Polar Surface Area: 63.60

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.41

CX Basic pKa: ┄

CX LogP: 6.15

CX LogD: 5.85

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.31

Np Likeness Score: 1.85

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