ethyl 3,4,5-trimethoxybenzyl hexylphosphonate

ID: ALA227845

PubChem CID: 16076986

Max Phase: Preclinical

Molecular Formula: C18H31O6P

Molecular Weight: 374.41

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Ethyl 3,4,5-Trimethoxybenzyl Hexylphosphonate | CHEMBL227845|ethyl 3,4,5-trimethoxybenzyl hexylphosphonate|BDBM50195744|5-[[ethoxy(hexyl)phosphoryl]oxymethyl]-1,2,3-trimethoxy-benzene|Phosphonic acid, hexyl-, ethyl (3,4,5-trimethoxyphenyl)methyl ester

Canonical SMILES:  CCCCCCP(=O)(OCC)OCc1cc(OC)c(OC)c(OC)c1

Standard InChI:  InChI=1S/C18H31O6P/c1-6-8-9-10-11-25(19,23-7-2)24-14-15-12-16(20-3)18(22-5)17(13-15)21-4/h12-13H,6-11,14H2,1-5H3

Standard InChI Key:  LACYNGJPKQCAMC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 25  0  0  0  0  0  0  0  0999 V2000
   -5.1549   -9.0002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4417   -8.5873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7285   -8.9960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0153   -8.5831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3022   -8.9918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5890   -8.5789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8758   -8.9877    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4671   -9.7008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2919   -8.4037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4598   -9.5715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5058   -8.6174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0896   -8.0336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3586   -9.7034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7692  -10.4199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3504  -11.1308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7603  -11.8468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5870  -11.8499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0020  -11.1310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5897  -10.4180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8278  -11.1307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2410  -11.8457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9986  -12.5657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5843  -13.2801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3448  -12.5604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4810  -12.5573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8 13  1  0
  6  7  1  0
 13 14  1  0
  3  4  1  0
 14 15  2  0
  7  8  1  0
 15 16  1  0
 16 17  2  0
  7  9  1  0
 17 18  1  0
  4  5  1  0
 18 19  2  0
 19 14  1  0
  7 10  2  0
 18 20  1  0
  2  3  1  0
 20 21  1  0
  9 11  1  0
 17 22  1  0
  5  6  1  0
 22 23  1  0
 11 12  1  0
 16 24  1  0
  1  2  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA227845

   Ethyl 3,4,5-trimethoxybenzyl hexylphosphonate

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: 374.41

Molecular Weight (Monoisotopic): 374.1858

AlogP: 5.04

#Rotatable Bonds: 13

Polar Surface Area: 63.22

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.51

CX LogD: 3.51

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.36

Np Likeness Score: 0.19

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