1-[(n-hept-1-ylamino)ethyl]-1,1-bisphosphonic acid

ID: ALA261473

PubChem CID: 13211563

Max Phase: Preclinical

Molecular Formula: C9H23NO6P2

Molecular Weight: 303.23

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C9H23NO6P2/c1-2-3-4-5-6-7-10-8-9(17(11,12)13)18(14,15)16/h9-10H,2-8H2,1H3,(H2,11,12,13)(H2,14,15,16)

Standard InChI Key:  WRMHTOUCTOHPIY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 18 17  0  0  0  0  0  0  0  0999 V2000
    1.9986    0.8111    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.7141   -0.4287    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.9986   -0.0031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8159    0.8111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2947   -1.1381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1689    0.8111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9986    1.6346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1213    0.2745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4173   -0.8358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2861   -0.4349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5675   -0.0124    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1449   -0.4195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8605   -0.0031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7165    0.0093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9979   -0.3979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5791   -0.4071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2947    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4382   -0.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  1  1  0
  4  1  2  0
  5  2  2  0
  6  1  1  0
  7  1  1  0
  8  2  1  0
  9  2  1  0
 10  3  1  0
 11 10  1  0
 12 11  1  0
 13 12  1  0
 14 15  1  0
 15 17  1  0
 16 13  1  0
 17 16  1  0
 18 14  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA261473

   [2-(Heptylamino)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: 303.23

Molecular Weight (Monoisotopic): 303.1001

AlogP: 1.23

#Rotatable Bonds: 10

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: 11.31

CX LogP: -1.64

CX LogD: -3.99

Aromatic Rings: ┄

Heavy Atoms: 18

QED Weighted: 0.30

Np Likeness Score: 0.19

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. Parrill AL, Echols U, Nguyen T, Pham TC, Hoeglund A, Baker DL..  (2008)  Virtual screening approaches for the identification of non-lipid autotaxin inhibitors.,  16  (4): [PMID:18036821] [10.1016/j.bmc.2007.11.018]

3. Rosso VS, Szajnman SH, Malayil L, Galizzi M, Moreno SN, Docampo R, Rodriguez JB..  (2011)  Synthesis and biological evaluation of new 2-alkylaminoethyl-1,1-bisphosphonic acids against Trypanosoma cruzi and Toxoplasma gondii targeting farnesyl diphosphate synthase.,  19  (7): [PMID:21419634] [10.1016/j.bmc.2011.02.037]

4. 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]

5. Ferrer-Casal M, Li C, Galizzi M, Stortz CA, Szajnman SH, Docampo R, Moreno SN, Rodriguez JB..  (2014)  New insights into molecular recognition of 1,1-bisphosphonic acids by farnesyl diphosphate synthase.,  22  (1): [PMID:24300918] [10.1016/j.bmc.2013.11.010]

6. Galaka T, Falcone BN, Li C, Szajnman SH, Moreno SNJ, Docampo R, Rodriguez JB..  (2019)  Synthesis and biological evaluation of 1-alkylaminomethyl-1,1-bisphosphonic acids against Trypanosoma cruzi and Toxoplasma gondii.,  27  (16): [PMID:31296439] [10.1016/j.bmc.2019.07.004]

Source

Source(1):

• Scientific Literature