1-[(n-Heptylthio)ethyl]-1,1-bisphosphonic acid

ID: ALA2326229

PubChem CID: 71574340

Max Phase: Preclinical

Molecular Formula: C9H22O6P2S

Molecular Weight: 320.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCSCC(P(=O)(O)O)P(=O)(O)O

Standard InChI:  InChI=1S/C9H22O6P2S/c1-2-3-4-5-6-7-18-8-9(16(10,11)12)17(13,14)15/h9H,2-8H2,1H3,(H2,10,11,12)(H2,13,14,15)

Standard InChI Key:  CGPFTXXMYYSRBQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 18 17  0  0  0  0  0  0  0  0999 V2000
   18.4941   -9.1624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9068   -8.4567    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   18.0893   -8.4521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1397   -8.4526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3225   -8.4526    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   20.7311   -9.1603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6167   -8.8653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3244   -7.6395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9090   -7.6395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6167   -9.6825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9090  -10.0911    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.9090  -10.9083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2013  -11.3169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2013  -12.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4936  -12.5426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4936  -13.3598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7859  -13.7684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7859  -14.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  5  4  1  0
  6  5  2  0
  7  5  1  0
  7  2  1  0
  5  8  1  0
  2  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2326229

   (2-Heptylsulfanyl-1-phosphonoethyl)phosphonic acid

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: 320.28

Molecular Weight (Monoisotopic): 320.0612

AlogP: 2.37

#Rotatable Bonds: 10

Polar Surface Area: 115.06

Molecular Species: ACID

HBA: 3

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.20

CX Basic pKa: ┄

CX LogP: 0.73

CX LogD: -4.01

Aromatic Rings: ┄

Heavy Atoms: 18

QED Weighted: 0.36

Np Likeness Score: 0.02

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]

3. Wu RZ, Zhou HY, Song JF, Xia QH, Hu W, Mou XD, Li X..  (2021)  Chemotherapeutics for Toxoplasma gondii: Molecular Biotargets, Binding Modes, and Structure-Activity Relationship Investigations.,  64  (24.0): [PMID:34894691] [10.1021/acs.jmedchem.1c01569]

Source

Source(1):

• Scientific Literature