(2,2-Diphosphonoethyl)(methyl)(octyl)sulfoniumtetrafluoroborate

ID: ALA2326222

PubChem CID: 71574532

Max Phase: Preclinical

Molecular Formula: C11H27BF4O6P2S

Molecular Weight: 349.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCC[S+](C)CC(P(=O)(O)O)P(=O)(O)O.F[B-](F)(F)F

Standard InChI:  InChI=1S/C11H26O6P2S.BF4/c1-3-4-5-6-7-8-9-20(2)10-11(18(12,13)14)19(15,16)17;2-1(3,4)5/h11H,3-10H2,1-2H3,(H3-,12,13,14,15,16,17);/q;-1/p+1

Standard InChI Key:  IRTQYBAMIQXTII-UHFFFAOYSA-O

Molfile:  

     RDKit          2D

 25 23  0  0  0  0  0  0  0  0999 V2000
    7.1442   -9.7196    0.0000 B   0  0  0  0  0  0  0  0  0  0  0  0
    7.8519   -9.3110    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.4365   -9.3110    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.1442  -10.5368    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.1401   -8.9024    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.2729  -12.0928    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.4445  -11.1642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8573  -10.4584    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.0397  -10.4538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0901  -10.4543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2729  -10.4543    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    3.6815  -11.1620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5671  -10.8670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2748   -9.6412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8594   -9.6412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5671  -11.6842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9826  -11.6842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6898  -12.0936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3980  -11.6859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1052  -12.0953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8134  -11.6876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2719  -12.9100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5206  -12.0970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2288  -11.6892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9360  -12.0987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  0
  1  4  1  0
  1  5  1  0
  8  7  2  0
  9  8  1  0
 11 10  1  0
 12 11  2  0
 13 11  1  0
 13  8  1  0
 11 14  1  0
  8 15  1  0
 13 16  1  0
 16  6  1  0
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
  6 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
M  CHG  2   1  -1   6   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: 349.35

Molecular Weight (Monoisotopic): 349.0998

AlogP: 2.28

#Rotatable Bonds: 11

Polar Surface Area: 115.06

Molecular Species: ACID

HBA: 2

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.15

CX Basic pKa: ┄

CX LogP: -0.11

CX LogD: -4.87

Aromatic Rings: ┄

Heavy Atoms: 20

QED Weighted: 0.26

Np Likeness Score: 0.41

References

1. Recher M, Barboza AP, Li ZH, Galizzi M, Ferrer-Casal M, Szajnman SH, Docampo R, Moreno SN, Rodriguez JB..  (2013)  Design, synthesis and biological evaluation of sulfur-containing 1,1-bisphosphonic acids as antiparasitic agents.,  60  [PMID:23318904] [10.1016/j.ejmech.2012.12.015]

2. Galaka T, Falcone BN, Li C, Szajnman SH, Moreno SNJ, Docampo R, Rodriguez JB..  (2019)  Synthesis and biological evaluation of 1-alkylaminomethyl-1,1-bisphosphonic acids against Trypanosoma cruzi and Toxoplasma gondii.,  27  (16): [PMID:31296439] [10.1016/j.bmc.2019.07.004]

Source

Source(1):

• Scientific Literature