1-[(Benzylamino)ethyl]1,1-bisphosphonic acid

ID: ALA1765145

PubChem CID: 19689053

Max Phase: Preclinical

Molecular Formula: C9H15NO6P2

Molecular Weight: 295.17

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 1-[(Benzylamino)Ethyl]1,1-Bisphosphonic Acid | CHEMBL1765145|1-[(Benzylamino)Ethyl]1,1-Bisphosphonic Acid|SCHEMBL8672391|BDBM50341910|[2-(benzylamino)-1-phosphono-ethyl]phosphonic acid

Canonical SMILES:  O=P(O)(O)C(CNCc1ccccc1)P(=O)(O)O

Standard InChI:  InChI=1S/C9H15NO6P2/c11-17(12,13)9(18(14,15)16)7-10-6-8-4-2-1-3-5-8/h1-5,9-10H,6-7H2,(H2,11,12,13)(H2,14,15,16)

Standard InChI Key:  JFBNFNDLCVVPAS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 18 18  0  0  0  0  0  0  0  0999 V2000
   -0.1207   -1.8912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5938   -1.4787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8351   -1.4787    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5938   -0.6538    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.3083   -1.8912    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.3083   -0.2412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2335   -0.6498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1751    0.0661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0227   -1.4787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8912   -2.5994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8873   -2.4672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5495   -1.8912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2640   -1.4787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2603   -0.6526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9739   -0.2403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6894   -0.6528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6867   -1.4821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9725   -1.8908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  5  1  0
  5 10  1  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  2  0
  2  4  1  0
 14 15  1  0
  4  8  1  0
 15 16  2  0
 16 17  1  0
  5  9  2  0
 17 18  2  0
 18 13  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1765145

   1-[(Benzylamino)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: 295.17

Molecular Weight (Monoisotopic): 295.0375

AlogP: 0.46

#Rotatable Bonds: 6

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: 10.24

CX LogP: -2.44

CX LogD: -4.79

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.48

Np Likeness Score: -0.37

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]

Source

Source(1):

• Scientific Literature