Benzoylphenoxy analogue

ID: ALA1160284

PubChem CID: 44302543

Max Phase: Preclinical

Molecular Formula: C18H20O9P2

Molecular Weight: 442.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C/C(=C\COP(=O)(O)OP(=O)(O)O)COc1ccc(C(=O)c2ccccc2)cc1

Standard InChI:  InChI=1S/C18H20O9P2/c1-14(11-12-26-29(23,24)27-28(20,21)22)13-25-17-9-7-16(8-10-17)18(19)15-5-3-2-4-6-15/h2-11H,12-13H2,1H3,(H,23,24)(H2,20,21,22)/b14-11+

Standard InChI Key:  ITZCSRRHGMNXSF-SDNWHVSQSA-N

Molfile:  

     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
   11.2417   -3.1167    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    9.9500   -3.2917    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   10.6625   -3.7042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8125   -4.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6542   -2.4042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9542   -3.5292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1625   -2.4917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0292   -2.3167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3625   -2.7042    0.0000 O   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
    2.8167   -5.8042    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   -4.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2375   -3.7167    0.0000 O   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
    4.2375   -4.9750    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
    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
    8.5167   -3.3042    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
    4.2292   -3.3167    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
    2.0917   -3.7417    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
    1.3792   -3.3292    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
    0.6667   -3.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  1  1  0
  4 10  1  0
  5  1  1  0
  6  1  1  0
  7  2  1  0
  8  1  2  0
  9  2  2  0
 10 17  2  0
 11  4  2  0
 12 15  2  0
 13  4  1  0
 14  2  1  0
 15 21  1  0
 16 22  2  0
 17 23  1  0
 18 20  1  0
 19 18  1  0
 20 12  1  0
 21 14  1  0
 22 19  1  0
 23 19  2  0
 24 12  1  0
 25 13  1  0
 26 13  2  0
 27 25  2  0
 28 26  1  0
 29 28  2  0
 16 10  1  0
 29 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1160284

   [(E)-4-(4-benzoylphenoxy)-3-methylbut-2-enyl] 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: 442.30

Molecular Weight (Monoisotopic): 442.0583

AlogP: 3.47

#Rotatable Bonds: 10

Polar Surface Area: 139.59

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.77

CX Basic pKa: ┄

CX LogP: 2.81

CX LogD: -2.22

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.29

Np Likeness Score: 0.58

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