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

ID: ALA4277675

PubChem CID: 87428975

Max Phase: Preclinical

Molecular Formula: C18H24O3

Molecular Weight: 288.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)=CCC/C(C)=C/Cc1c(O)cc(C)c(C=O)c1O

Standard InChI:  InChI=1S/C18H24O3/c1-12(2)6-5-7-13(3)8-9-15-17(20)10-14(4)16(11-19)18(15)21/h6,8,10-11,20-21H,5,7,9H2,1-4H3/b13-8+

Standard InChI Key:  SXOCWLUWTFGULD-MDWZMJQESA-N

Molfile:  

     RDKit          2D

 21 21  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
   12.1378  -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
  7 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4277675

   3-[(2E)-3,7-dimethylocta-2,6-dienyl]-2,4-dihydroxy-6-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: 288.39

Molecular Weight (Monoisotopic): 288.1725

AlogP: 4.45

#Rotatable Bonds: 6

Polar Surface Area: 57.53

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.33

CX Basic pKa: ┄

CX LogP: 5.63

CX LogD: 5.29

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.60

Np Likeness Score: 2.19

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