1-[(cyclohexylamino)ethyl]-1,1-bisphosphonic acid

ID: ALA261432

Cas Number: 146829-50-7

PubChem CID: 21803454

Max Phase: Preclinical

Molecular Formula: C8H19NO6P2

Molecular Weight: 287.19

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=P(O)(O)C(CNC1CCCCC1)P(=O)(O)O

Standard InChI:  InChI=1S/C8H19NO6P2/c10-16(11,12)8(17(13,14)15)6-9-7-4-2-1-3-5-7/h7-9H,1-6H2,(H2,10,11,12)(H2,13,14,15)

Standard InChI Key:  OAHUDYBQKIUBMC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 17 17  0  0  0  0  0  0  0  0999 V2000
   10.7846   -4.6384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7846   -5.4634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0701   -4.2259    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   11.4991   -4.2259    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   12.2054   -3.8041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3546   -3.8134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4823   -3.5112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6587   -4.9409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9167   -4.9372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0834   -3.5132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0701   -5.8759    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0701   -6.7009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3556   -7.1134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3556   -7.9384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7846   -7.1134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7846   -7.9384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0701   -8.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
  1  4  1  0
 12 15  1  0
  3  8  1  0
 15 16  1  0
 14 17  1  0
 16 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA261432

   [2-(Cyclohexylamino)ethane-1,1-Diyl]bisphosphonic 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: 287.19

Molecular Weight (Monoisotopic): 287.0688

AlogP: 0.59

#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: 11.49

CX LogP: -2.47

CX LogD: -4.82

Aromatic Rings: ┄

Heavy Atoms: 17

QED Weighted: 0.47

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]

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