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

ID: ALA1765146

PubChem CID: 13211564

Max Phase: Preclinical

Molecular Formula: C11H27NO6P2

Molecular Weight: 331.29

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C11H27NO6P2/c1-2-3-4-5-6-7-8-9-12-10-11(19(13,14)15)20(16,17)18/h11-12H,2-10H2,1H3,(H2,13,14,15)(H2,16,17,18)

Standard InChI Key:  DXTYOSQHSRZDRD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 19  0  0  0  0  0  0  0  0999 V2000
   10.8354   -1.4861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5515   -1.0725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1192   -1.0725    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5515   -0.2458    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   12.2677   -1.4861    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   12.2677    0.1678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7223   -0.2418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1317    0.4759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9837   -1.0725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8495   -2.1958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8479   -2.0634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4040   -1.4861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6901   -1.0725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9764   -1.4861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2625   -1.0725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5489   -1.4861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8350   -1.0725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1211   -1.4861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4074   -1.0725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6936   -1.4861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  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
M  END

Alternative Forms

1. Parent:

   

   ALA1765146

   1-[(n-Non-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: 331.29

Molecular Weight (Monoisotopic): 331.1314

AlogP: 2.01

#Rotatable Bonds: 12

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: -0.80

CX LogD: -3.15

Aromatic Rings: ┄

Heavy Atoms: 20

QED Weighted: 0.27

Np Likeness Score: 0.17

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