1-[(tert-butylamino)ethyl]-1,1-bisphosphonic acid

ID: ALA405827

PubChem CID: 19689018

Max Phase: Preclinical

Molecular Formula: C6H17NO6P2

Molecular Weight: 261.15

Molecule Type: Small molecule

Names and Identifiers

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

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

Standard InChI Key:  XGRIOZQTBVXIFW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 15 14  0  0  0  0  0  0  0  0999 V2000
    6.0729   -4.7712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0729   -5.5962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3584   -4.3587    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    6.7874   -4.3587    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    7.4937   -3.9371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6429   -3.9462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7707   -3.6442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9469   -5.0739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2051   -5.0702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3717   -3.6461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3584   -6.0087    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3584   -6.8337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3534   -7.6541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1834   -6.8363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5334   -6.8357    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
 12 14  1  0
  1  4  1  0
 12 15  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA405827

   [2-(Tert-butylamino)-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: 0.06

#Rotatable Bonds: 4

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: 0.70

CX Basic pKa: 11.22

CX LogP: -3.25

CX LogD: -5.60

Aromatic Rings: ┄

Heavy Atoms: 15

QED Weighted: 0.45

Np Likeness Score: -0.03

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