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

ID: ALA407221

PubChem CID: 19689020

Max Phase: Preclinical

Molecular Formula: C5H15NO6P2

Molecular Weight: 247.12

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C5H15NO6P2/c1-4(2)6-3-5(13(7,8)9)14(10,11)12/h4-6H,3H2,1-2H3,(H2,7,8,9)(H2,10,11,12)

Standard InChI Key:  XUKNZUJYUAFJQJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 14 13  0  0  0  0  0  0  0  0999 V2000
   15.8495   -5.0189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8495   -5.8439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1350   -4.6064    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   16.5641   -4.6064    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   17.2704   -4.1847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4194   -4.1938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5473   -3.8918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7235   -5.3215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9817   -5.3178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1484   -3.8936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1350   -6.2564    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1350   -7.0814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4205   -7.4939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8495   -7.4939    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  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
M  END

Alternative Forms

1. Parent:

   

   ALA407221

   [2-(Isopropylamino)-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: 247.12

Molecular Weight (Monoisotopic): 247.0375

AlogP: -0.33

#Rotatable Bonds: 5

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: 11.15

CX LogP: -3.41

CX LogD: -5.76

Aromatic Rings: ┄

Heavy Atoms: 14

QED Weighted: 0.42

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