5-[(Triphenylphosphonio)methyl]-2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin chloride

ID: ALA2398202

PubChem CID: 24191648

Max Phase: Preclinical

Molecular Formula: C29H29ClNO2P

Molecular Weight: 454.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ncc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)c2c1OC(C)(C)OC2.[Cl-]

Standard InChI:  InChI=1S/C29H29NO2P.ClH/c1-22-28-27(20-31-29(2,3)32-28)23(19-30-22)21-33(24-13-7-4-8-14-24,25-15-9-5-10-16-25)26-17-11-6-12-18-26;/h4-19H,20-21H2,1-3H3;1H/q+1;/p-1

Standard InChI Key:  LZBUAIQPDDLCQR-UHFFFAOYSA-M

Molfile:  

     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
    6.7480   -3.3431    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.9501   -5.4007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6582   -5.8097    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3678   -5.4002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3650   -4.5776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2421   -5.8088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0712   -4.1663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7804   -4.5723    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    7.7835   -5.3894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0782   -5.7976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0809   -6.6140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7907   -7.0207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4992   -6.6051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4930   -5.7900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2190   -3.8763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0415   -3.9104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4793   -3.2155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0956   -2.4874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2698   -2.4585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8357   -3.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5681   -4.7793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7803   -5.5668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5672   -5.7740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1413   -5.1951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9232   -4.4060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1367   -4.2024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9513   -4.5812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6578   -4.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6585   -3.3632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9544   -2.9532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2478   -3.3603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2455   -4.1774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4545   -3.5701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6650   -2.7776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 27  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5 28  2  0
  2  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
  8 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
  8 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 27 28  1  0
 27 32  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 31 33  1  0
 31 34  1  0
M  CHG  2   1  -1   8   1
M  END

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: 454.53

Molecular Weight (Monoisotopic): 454.1930

AlogP: 5.53

#Rotatable Bonds: 5

Polar Surface Area: 31.35

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 4.97

CX LogP: 5.40

CX LogD: 5.40

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.37

Np Likeness Score: 0.22

References

1. Pugachev MV, Shtyrlin NV, Sysoeva LP, Nikitina EV, Abdullin TI, Iksanova AG, Ilaeva AA, Musin RZ, Berdnikov EA, Shtyrlin YG..  (2013)  Synthesis and antibacterial activity of novel phosphonium salts on the basis of pyridoxine.,  21  (14): [PMID:23683836] [10.1016/j.bmc.2013.04.051]

Source

Source(1):

• Scientific Literature