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

ID: ALA1765149

PubChem CID: 53248992

Max Phase: Preclinical

Molecular Formula: C14H33NO6P2

Molecular Weight: 373.37

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C14H33NO6P2/c1-2-3-4-5-6-7-8-9-10-11-12-15-13-14(22(16,17)18)23(19,20)21/h14-15H,2-13H2,1H3,(H2,16,17,18)(H2,19,20,21)

Standard InChI Key:  MTPROXDBHCNBRU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 22  0  0  0  0  0  0  0  0999 V2000
   11.9361   -7.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6522   -6.8300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2199   -6.8300    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6522   -6.0032    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   13.3684   -7.2436    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   13.3684   -5.5896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8230   -5.9992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2326   -5.2815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0846   -6.8300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9502   -7.9535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9488   -7.8209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5045   -7.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7907   -6.8300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0769   -7.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3630   -6.8300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6492   -7.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9354   -6.8300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2216   -7.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5077   -6.8300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7939   -7.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0772   -6.8311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3617   -7.2456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6448   -6.8331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
  5 11  1  0
 21 22  1  0
  4  6  2  0
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1765149

   1-[(n-Dodec-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: 373.37

Molecular Weight (Monoisotopic): 373.1783

AlogP: 3.18

#Rotatable Bonds: 15

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: 0.46

CX LogD: -1.89

Aromatic Rings: ┄

Heavy Atoms: 23

QED Weighted: 0.22

Np Likeness Score: 0.15

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. Ferrer-Casal M, Li C, Galizzi M, Stortz CA, Szajnman SH, Docampo R, Moreno SN, Rodriguez JB..  (2014)  New insights into molecular recognition of 1,1-bisphosphonic acids by farnesyl diphosphate synthase.,  22  (1): [PMID:24300918] [10.1016/j.bmc.2013.11.010]

3. 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]

4. 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