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

ID: ALA258541

PubChem CID: 44451320

Max Phase: Preclinical

Molecular Formula: C6H16N2O6P2

Molecular Weight: 274.15

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=P(O)(O)C(CNN1CCCC1)P(=O)(O)O

Standard InChI:  InChI=1S/C6H16N2O6P2/c9-15(10,11)6(16(12,13)14)5-7-8-3-1-2-4-8/h6-7H,1-5H2,(H2,9,10,11)(H2,12,13,14)

Standard InChI Key:  JVRKRFPWDJALRO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 16 16  0  0  0  0  0  0  0  0999 V2000
   -0.9571   -1.1608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9571   -1.9858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6716   -0.7483    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2426   -0.7483    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.4637   -0.3267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3871   -0.3358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2594   -0.0337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0830   -1.4634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1750   -1.4598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6583   -0.0356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6716   -2.3983    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6716   -3.2233    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3380   -3.7109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0831   -4.4956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2580   -4.4955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0032   -3.7109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
  3  7  1  0
  1  4  1  0
 12 13  1  0
  3  8  1  0
  4  9  1  0
  4  5  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 12  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA258541

   [1-Phosphono-2-(pyrrolidin-1-ylamino)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: 274.15

Molecular Weight (Monoisotopic): 274.0484

AlogP: -0.73

#Rotatable Bonds: 5

Polar Surface Area: 130.33

Molecular Species: ACID

HBA: 4

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 0.50

CX Basic pKa: 6.39

CX LogP: -4.46

CX LogD: -6.95

Aromatic Rings: ┄

Heavy Atoms: 16

QED Weighted: 0.41

Np Likeness Score: -0.14

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