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

ID: ALA2326232

PubChem CID: 71574435

Max Phase: Preclinical

Molecular Formula: C12H28O6P2S

Molecular Weight: 362.37

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C12H28O6P2S/c1-2-3-4-5-6-7-8-9-10-21-11-12(19(13,14)15)20(16,17)18/h12H,2-11H2,1H3,(H2,13,14,15)(H2,16,17,18)

Standard InChI Key:  CVEAKFSSPKASQL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 20  0  0  0  0  0  0  0  0999 V2000
   14.6558  -16.6451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0685  -15.9394    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   14.2509  -15.9348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3013  -15.9352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4842  -15.9352    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   16.8927  -16.6429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7784  -16.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4861  -15.1222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0707  -15.1222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7784  -17.1651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0707  -17.5737    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.0707  -18.3909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3630  -18.7995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3630  -19.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6553  -20.0253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6553  -20.8425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9476  -21.2511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9476  -22.0683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2399  -22.4769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2399  -23.2941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5321  -23.7027    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
 18 19  1  0
 19 20  1  0
 20 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2326232

   (2-Decylsulfanyl-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: 362.37

Molecular Weight (Monoisotopic): 362.1082

AlogP: 3.54

#Rotatable Bonds: 13

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: 1.99

CX LogD: -2.75

Aromatic Rings: ┄

Heavy Atoms: 21

QED Weighted: 0.29

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]

Source

Source(1):

• Scientific Literature