ethyl 3-phenoxybenzyl tetradecylphosphonate

ID: ALA387718

PubChem CID: 44423067

Max Phase: Preclinical

Molecular Formula: C29H45O4P

Molecular Weight: 488.65

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Ethyl 3-Phenoxybenzyl Tetradecylphosphonate | CHEMBL387718|ethyl 3-phenoxybenzyl tetradecylphosphonate|BDBM50195745

Canonical SMILES:  CCCCCCCCCCCCCCP(=O)(OCC)OCc1ccccc1Oc1ccccc1

Standard InChI:  InChI=1S/C29H45O4P/c1-3-5-6-7-8-9-10-11-12-13-14-20-25-34(30,31-4-2)32-26-27-21-18-19-24-29(27)33-28-22-16-15-17-23-28/h15-19,21-24H,3-14,20,25-26H2,1-2H3

Standard InChI Key:  AFQBKIVZNQKUMU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   15.3728   -4.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9439   -4.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0873   -4.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   20.3963   -6.3552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1157   -6.7575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8252   -6.3350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8109   -5.5058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0910   -5.1072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8016   -4.8120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0710   -4.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0375   -3.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3069   -3.2214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6098   -3.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8791   -3.2794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8096   -5.7706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9846   -5.7751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  9  1  0
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  2  4  1  0
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 14 15  2  0
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 31 32  1  0
  7 33  1  0
 16 17  2  0
 33 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA387718

   Ethyl 3-phenoxybenzyl tetradecylphosphonate

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: 488.65

Molecular Weight (Monoisotopic): 488.3055

AlogP: 9.93

#Rotatable Bonds: 20

Polar Surface Area: 44.76

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 8.91

CX LogD: 8.91

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.14

Np Likeness Score: -0.13

References

1. Gobec S, Plantan I, Mravljak J, Svajger U, Wilson RA, Besra GS, Soares SL, Appelberg R, Kikelj D..  (2007)  Design, synthesis, biochemical evaluation and antimycobacterial action of phosphonate inhibitors of antigen 85C, a crucial enzyme involved in biosynthesis of the mycobacterial cell wall.,  42  (1): [PMID:17010479] [10.1016/j.ejmech.2006.08.007]

Source

Source(1):

• Scientific Literature