Benzoylphenoxy analogue

ID: ALA1160285

PubChem CID: 10324054

Max Phase: Preclinical

Molecular Formula: C23H28O9P2

Molecular Weight: 510.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C/C(=C\COP(=O)(O)OP(=O)(O)O)CC/C=C(\C)COc1cccc(C(=O)c2ccccc2)c1

Standard InChI:  InChI=1S/C23H28O9P2/c1-18(14-15-31-34(28,29)32-33(25,26)27)8-6-9-19(2)17-30-22-13-7-12-21(16-22)23(24)20-10-4-3-5-11-20/h3-5,7,9-14,16H,6,8,15,17H2,1-2H3,(H,28,29)(H2,25,26,27)/b18-14+,19-9+

Standard InChI Key:  ALCZOXVCEVZROP-KKEAHIQDSA-N

Molfile:  

     RDKit          2D

 34 35  0  0  0  0  0  0  0  0999 V2000
   14.1042   -3.1125    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   12.8042   -3.2875    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   13.5167   -3.7000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8042   -3.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5250   -3.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8167   -3.5250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5125   -2.3917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0167   -2.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8875   -2.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2167   -2.7000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2292   -3.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8042   -2.5000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0917   -3.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0917   -3.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0917   -3.7042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9500   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8042   -3.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6667   -3.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6625   -3.3167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500   -3.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3792   -3.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3792   -3.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5167   -3.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5167   -4.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2375   -4.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2375   -3.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0875   -2.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9417   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0917   -4.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3792   -3.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9542   -4.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3792   -4.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6667   -3.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6667   -4.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  1  1  0
  4  5  1  0
  5 11  1  0
  6  1  1  0
  7  1  1  0
  8  2  1  0
  9  1  2  0
 10  2  2  0
 11 20  2  0
 12  4  2  0
 13 17  2  0
 14  4  1  0
 15  2  1  0
 16 18  2  0
 17 23  1  0
 18 22  1  0
 19 21  1  0
 20 19  1  0
 21 13  1  0
 22 15  1  0
 23 26  1  0
 24 25  1  0
 25 31  2  0
 26 16  1  0
 27 13  1  0
 28 16  1  0
 29 14  1  0
 30 14  2  0
 31 20  1  0
 32 29  2  0
 33 30  1  0
 34 33  2  0
 24  5  2  0
 32 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1160285

   [(2E,6E)-8-(3-benzoylphenoxy)-3,7-dimethylocta-2,6-dienyl] phosphono hydrogen phosphate

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: 510.42

Molecular Weight (Monoisotopic): 510.1209

AlogP: 5.20

#Rotatable Bonds: 13

Polar Surface Area: 139.59

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.77

CX Basic pKa: ┄

CX LogP: 4.47

CX LogD: -0.56

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.19

Np Likeness Score: 0.80

References

1. Marecak DM, Horiuchi Y, Arai H, Shimonaga M, Maki Y, Koyama T, Ogura K, Prestwich GD.  (1997)  Benzoylphenoxy analogs of isoprenoid diphosphates as photoactivatable substrates for bacterial prenyltransferases,  7  (15): [10.1016/S0960-894X(97)00342-9]

Source

Source(1):

• Scientific Literature