1-[(prop-1-ylamino)ethyl]-1,1-bisphosphonic acid

ID: ALA408745

PubChem CID: 15390273

Max Phase: Preclinical

Molecular Formula: C5H15NO6P2

Molecular Weight: 247.12

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C5H15NO6P2/c1-2-3-6-4-5(13(7,8)9)14(10,11)12/h5-6H,2-4H2,1H3,(H2,7,8,9)(H2,10,11,12)

Standard InChI Key:  YFFJUBPLIKXHAO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 14 13  0  0  0  0  0  0  0  0999 V2000
   -3.7491    2.4704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7491    1.6454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4637    2.8829    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0347    2.8829    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3284    3.3046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1791    3.2954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0514    3.5976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8751    2.1679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6170    2.1715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4504    3.5956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4637    1.2329    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4637    0.4079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1781   -0.0046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1781   -0.8296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0
  3  8  1  0
  4  9  1  0
  4  5  2  0
  4 10  1  0
  1  3  1  0
  2 11  1  0
  3  6  1  0
 11 12  1  0
  1  2  1  0
 12 13  1  0
  3  7  2  0
 13 14  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA408745

   [2-(Propylamino)ethane-1,1-Diyl]bis(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: 247.12

Molecular Weight (Monoisotopic): 247.0375

AlogP: -0.33

#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: 11.25

CX LogP: -3.32

CX LogD: -5.67

Aromatic Rings: ┄

Heavy Atoms: 14

QED Weighted: 0.32

Np Likeness Score: 0.06

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]

2. Aripirala S, Szajnman SH, Jakoncic J, Rodriguez JB, Docampo R, Gabelli SB, Amzel LM..  (2012)  Design, synthesis, calorimetry, and crystallographic analysis of 2-alkylaminoethyl-1,1-bisphosphonates as inhibitors of Trypanosoma cruzi farnesyl diphosphate synthase.,  55  (14): [PMID:22715997] [10.1021/jm300425y]

Source

Source(1):

• Scientific Literature