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

ID: ALA4294528

Cas Number: 83324-48-5

PubChem CID: 6439644

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/Cc1c(O)c(Cl)c(C)c(C=O)c1O

Standard InChI:  InChI=1S/C18H23ClO3/c1-11(2)6-5-7-12(3)8-9-14-17(21)15(10-20)13(4)16(19)18(14)22/h6,8,10,21-22H,5,7,9H2,1-4H3/b12-8+

Standard InChI Key:  UEUMAXMCCDEOIJ-XYOKQWHBSA-N

Molfile:  

     RDKit          2D

 22 22  0  0  0  0  0  0  0  0999 V2000
   10.1988  -14.0814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1988  -13.2559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4833  -12.8452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4833  -12.0196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1988  -11.6047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9143  -12.0196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9143  -12.8452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7678  -11.6047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6298  -11.6047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1988  -10.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4833  -10.3684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6298  -13.2559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3452  -12.8452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0566  -13.2559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7721  -12.8452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4876  -13.2559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2031  -12.8452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9187  -13.2559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6342  -12.8452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9187  -14.0814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0566  -14.0814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7678  -13.2559    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  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
  4  8  1  0
  6  9  1  0
 10 11  2  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
  7 12  1  0
  3 22  1  0
  1  2  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4294528

   3-Chloro-5-[(2e)-3,7-Dimethylocta-2,6-Dien-1-Yl]-4,6-Dihydroxy-2-Methylbenzaldehyde

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: 5.11

#Rotatable Bonds: 6

Polar Surface Area: 57.53

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 5.84

CX Basic pKa: ┄

CX LogP: 6.23

CX LogD: 4.75

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.57

Np Likeness Score: 2.00

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]

2. Kemkuignou BM, Moussa AY, Decock C, Stadler M..  (2022)  Terpenoids and Meroterpenoids from Cultures of Two Grass-Associated Species of Amylosporus (Basidiomycota).,  85  (4.0): [PMID:35175766] [10.1021/acs.jnatprod.1c00975]

Source

Source(1):

• Scientific Literature