3-Chloro-5-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-4,6-dihydroxy-2-methylbenzonitrile

ID: ALA4291644

PubChem CID: 72194942

Max Phase: Preclinical

Molecular Formula: C18H22ClNO2

Molecular Weight: 319.83

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)=CCC/C(C)=C/Cc1c(O)c(Cl)c(C)c(C#N)c1O

Standard InChI:  InChI=1S/C18H22ClNO2/c1-11(2)6-5-7-12(3)8-9-14-17(21)15(10-20)13(4)16(19)18(14)22/h6,8,21-22H,5,7,9H2,1-4H3/b12-8+

Standard InChI Key:  KMUONCCIWYOKLS-XYOKQWHBSA-N

Molfile:  

     RDKit          2D

 22 22  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
   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
   12.1390  -11.1565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5747   -9.5059    0.0000 N   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
  5  8  1  0
  3  9  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 12 19  1  0
  4 10  1  0
  6 20  1  0
  7 21  1  0
  1 22  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA4291644

   5-chloro-3-[(2E)-3,7-dimethylocta-2,6-dienyl]-2,4-dihydroxy-6-methylbenzonitrile

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: 319.83

Molecular Weight (Monoisotopic): 319.1339

AlogP: 5.17

#Rotatable Bonds: 5

Polar Surface Area: 64.25

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 6.33

CX Basic pKa: ┄

CX LogP: 5.73

CX LogD: 4.61

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.74

Np Likeness Score: 1.34

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