1-(but-2-ylamino)ethyl 1,I-bisphosphonic acid

ID: ALA262598

PubChem CID: 44451344

Max Phase: Preclinical

Molecular Formula: C6H17NO6P2

Molecular Weight: 261.15

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C6H17NO6P2/c1-3-5(2)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:  BDBDLQIJTHDVGZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 15 14  0  0  0  0  0  0  0  0999 V2000
   10.4567   -3.1276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4567   -3.9526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7422   -2.7151    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   11.1711   -2.7151    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   11.8775   -2.2935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0266   -2.3026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1545   -2.0006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3307   -3.4302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5888   -3.4266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7555   -2.0024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7422   -4.3651    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7422   -5.1902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0277   -5.6027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0277   -6.4277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4567   -5.6027    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
 12 15  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA262598

   [1-Phosphono-2-(sec-butylamino)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: 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: 0.70

CX Basic pKa: 11.32

CX LogP: -2.91

CX LogD: -5.26

Aromatic Rings: ┄

Heavy Atoms: 15

QED Weighted: 0.43

Np Likeness Score: -0.22

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