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

ID: ALA4285614

PubChem CID: 145990606

Max Phase: Preclinical

Molecular Formula: C20H26O4

Molecular Weight: 330.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)Oc1cc(C)c(C=O)c(O)c1C/C=C(\C)CCC=C(C)C

Standard InChI:  InChI=1S/C20H26O4/c1-13(2)7-6-8-14(3)9-10-17-19(24-16(5)22)11-15(4)18(12-21)20(17)23/h7,9,11-12,23H,6,8,10H2,1-5H3/b14-9+

Standard InChI Key:  LYHCQJLNAHLKIV-NTEUORMPSA-N

Molfile:  

     RDKit          2D

 24 24  0  0  0  0  0  0  0  0999 V2000
   13.5734  -10.3299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5734  -11.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2888  -11.5702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2888  -12.3956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5734  -12.8063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8579  -12.3956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8579  -11.5702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8579   -9.9192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5734  -13.6318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0042  -11.1554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0042  -12.8063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7155  -12.3956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4309  -12.8063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1463  -12.3956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8618  -12.8063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5772  -12.3956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2926  -12.8063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0081  -12.3956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2926  -13.6318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4309  -13.6318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8536  -14.0472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8536  -14.8782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1340  -13.6318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1378  -11.1554    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
  9 21  1  0
 21 22  1  0
 21 23  2  0
  7 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4285614

   ---

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: 330.42

Molecular Weight (Monoisotopic): 330.1831

AlogP: 4.67

#Rotatable Bonds: 7

Polar Surface Area: 63.60

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.81

CX Basic pKa: ┄

CX LogP: 5.54

CX LogD: 5.40

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.34

Np Likeness Score: 2.05

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