1-[(n-Dec-1-ylamino)ethyl]1,1-bisphosphonic acid

ID: ALA1765147

PubChem CID: 54584170

Max Phase: Preclinical

Molecular Formula: C12H29NO6P2

Molecular Weight: 345.31

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C12H29NO6P2/c1-2-3-4-5-6-7-8-9-10-13-11-12(20(14,15)16)21(17,18)19/h12-13H,2-11H2,1H3,(H2,14,15,16)(H2,17,18,19)

Standard InChI Key:  HRIDUOZZXIYDCR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 20  0  0  0  0  0  0  0  0999 V2000
   22.3694   -0.7451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0856   -0.3316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6531   -0.3316    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.0856    0.4955    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   23.8018   -0.7451    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   23.8018    0.9089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2562    0.4993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6658    1.2172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5180   -0.3316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3836   -1.4552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.3824   -1.3225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9376   -0.7451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2237   -0.3316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5098   -0.7451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7959   -0.3316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0819   -0.7451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3680   -0.3316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6541   -0.7451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9402   -0.3316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2263   -0.7451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5095   -0.3326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5 11  1  0
  4  6  2  0
  3 12  1  0
  1  2  1  0
 12 13  1  0
  4  7  1  0
 13 14  1  0
  2  4  1  0
 14 15  1  0
  4  8  1  0
 15 16  1  0
 16 17  1  0
  5  9  2  0
 17 18  1  0
  2  5  1  0
 18 19  1  0
  5 10  1  0
 19 20  1  0
  1  3  1  0
 20 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1765147

   1-[(n-Dec-1-ylamino)ethyl]1,1-bisphosphonic 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: 345.31

Molecular Weight (Monoisotopic): 345.1470

AlogP: 2.40

#Rotatable Bonds: 13

Polar Surface Area: 127.09

Molecular Species: ZWITTERION

HBA: 3

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 0.71

CX Basic pKa: 11.31

CX LogP: -0.38

CX LogD: -2.73

Aromatic Rings: ┄

Heavy Atoms: 21

QED Weighted: 0.26

Np Likeness Score: 0.16

References

1. Rosso VS, Szajnman SH, Malayil L, Galizzi M, Moreno SN, Docampo R, Rodriguez JB..  (2011)  Synthesis and biological evaluation of new 2-alkylaminoethyl-1,1-bisphosphonic acids against Trypanosoma cruzi and Toxoplasma gondii targeting farnesyl diphosphate synthase.,  19  (7): [PMID:21419634] [10.1016/j.bmc.2011.02.037]

2. 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