1-[(2-methylprop-1-ylamino)ethyl]-1,1-bisphosphonic acid

ID: ALA258540

PubChem CID: 15390278

Max Phase: Preclinical

Molecular Formula: C6H17NO6P2

Molecular Weight: 261.15

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)CNCC(P(=O)(O)O)P(=O)(O)O

Standard InChI:  InChI=1S/C6H17NO6P2/c1-5(2)3-7-4-6(14(8,9)10)15(11,12)13/h5-7H,3-4H2,1-2H3,(H2,8,9,10)(H2,11,12,13)

Standard InChI Key:  DBYTXQQWCVBPQR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 15 14  0  0  0  0  0  0  0  0999 V2000
    1.1596  -11.4400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1596  -12.2650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4451  -11.0275    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.8741  -11.0275    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.5804  -10.6059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2704  -10.6150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8573  -10.3129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0337  -11.7426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2917  -11.7390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4584  -10.3148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4451  -12.6775    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4451  -13.5025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2694  -13.9150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2694  -14.7400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9838  -13.5025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  8  1  0
  4  9  1  0
  4  5  1  0
  4 10  2  0
  1  3  1  0
  2 11  1  0
  3  6  2  0
 11 12  1  0
  1  2  1  0
 12 13  1  0
  3  7  1  0
 13 14  1  0
  1  4  1  0
 13 15  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA258540

   [2-(Isobutylamino)-1-phosphono-ethyl]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: 261.15

Molecular Weight (Monoisotopic): 261.0531

AlogP: -0.09

#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: 11.43

CX LogP: -2.94

CX LogD: -5.29

Aromatic Rings: ┄

Heavy Atoms: 15

QED Weighted: 0.42

Np Likeness Score: 0.04

References

1. Szajnman SH, García Liñares GE, Li ZH, Jiang C, Galizzi M, Bontempi EJ, Ferella M, Moreno SN, Docampo R, Rodriguez JB..  (2008)  Synthesis and biological evaluation of 2-alkylaminoethyl-1,1-bisphosphonic acids against Trypanosoma cruzi and Toxoplasma gondii targeting farnesyl diphosphate synthase.,  16  (6): [PMID:18096393] [10.1016/j.bmc.2007.12.010]

Source

Source(1):

• Scientific Literature