[(4-Methyl-pyridin-2-ylamino)-phosphono-methyl]-phosphonic acid

ID: ALA55557

PubChem CID: 5276543

Max Phase: Preclinical

Molecular Formula: C7H12N2O6P2

Molecular Weight: 282.13

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccnc(NC(P(=O)(O)O)P(=O)(O)O)c1

Standard InChI:  InChI=1S/C7H12N2O6P2/c1-5-2-3-8-6(4-5)9-7(16(10,11)12)17(13,14)15/h2-4,7H,1H3,(H,8,9)(H2,10,11,12)(H2,13,14,15)

Standard InChI Key:  BAYFWSDXNJQZPY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 17 17  0  0  0  0  0  0  0  0999 V2000
    4.6167   -1.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6167   -0.3375    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.6167   -1.9875    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    5.4792   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9417   -1.7750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0667   -1.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4042   -0.2750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4417   -1.9917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7917   -1.9875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7917   -0.3375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6167    0.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6167   -2.8125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7417   -2.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5292   -2.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3167   -3.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2167   -3.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0042   -4.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  1  1  0
  5  6  1  0
  6  4  1  0
  7  2  2  0
  8  3  2  0
  9  3  1  0
 10  2  1  0
 11  2  1  0
 12  3  1  0
 13  6  2  0
 14  5  2  0
 15 13  1  0
 16 15  2  0
 17 15  1  0
 14 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA55557

   2-[(Bis-phosphono-methyl)-amino]-4-methyl-pyridinium

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: 282.13

Molecular Weight (Monoisotopic): 282.0171

AlogP: 0.44

#Rotatable Bonds: 4

Polar Surface Area: 139.98

Molecular Species: ACID

HBA: 4

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 0.87

CX Basic pKa: 7.11

CX LogP: -2.09

CX LogD: -5.03

Aromatic Rings: 1

Heavy Atoms: 17

QED Weighted: 0.50

Np Likeness Score: -0.54

References

1. Ghosh S, Chan JM, Lea CR, Meints GA, Lewis JC, Tovian ZS, Flessner RM, Loftus TC, Bruchhaus I, Kendrick H, Croft SL, Kemp RG, Kobayashi S, Nozaki T, Oldfield E..  (2004)  Effects of bisphosphonates on the growth of Entamoeba histolytica and Plasmodium species in vitro and in vivo.,  47  (1): [PMID:14695831] [10.1021/jm030084x]

2. Szabo CM, Matsumura Y, Fukura S, Martin MB, Sanders JM, Sengupta S, Cieslak JA, Loftus TC, Lea CR, Lee HJ, Koohang A, Coates RM, Sagami H, Oldfield E..  (2002)  Inhibition of geranylgeranyl diphosphate synthase by bisphosphonates and diphosphates: a potential route to new bone antiresorption and antiparasitic agents.,  45  (11): [PMID:12014956] [10.1021/jm010412y]

3. Szabo CM, Martin MB, Oldfield E..  (2002)  An investigation of bone resorption and Dictyostelium discoideum growth inhibition by bisphosphonate drugs.,  45  (14): [PMID:12086477] [10.1021/jm010279+]

4. Martin MB, Sanders JM, Kendrick H, de Luca-Fradley K, Lewis JC, Grimley JS, Van Brussel EM, Olsen JR, Meints GA, Burzynska A, Kafarski P, Croft SL, Oldfield E..  (2002)  Activity of bisphosphonates against Trypanosoma brucei rhodesiense.,  45  (14): [PMID:12086478] [10.1021/jm0102809]

5. Sanders JM, Ghosh S, Chan JM, Meints G, Wang H, Raker AM, Song Y, Colantino A, Burzynska A, Kafarski P, Morita CT, Oldfield E..  (2004)  Quantitative structure-activity relationships for gammadelta T cell activation by bisphosphonates.,  47  (2): [PMID:14711309] [10.1021/jm0303709]

6. Sanders JM, Gómez AO, Mao J, Meints GA, Van Brussel EM, Burzynska A, Kafarski P, González-Pacanowska D, Oldfield E..  (2003)  3-D QSAR investigations of the inhibition of Leishmania major farnesyl pyrophosphate synthase by bisphosphonates.,  46  (24): [PMID:14613320] [10.1021/jm0302344]

7. Ling Y, Sahota G, Odeh S, Chan JM, Araujo FG, Moreno SN, Oldfield E..  (2005)  Bisphosphonate inhibitors of Toxoplasma gondi growth: in vitro, QSAR, and in vivo investigations.,  48  (9): [PMID:15857119] [10.1021/jm040132t]

8. Prado-Prado FJ, García-Mera X, González-Díaz H..  (2010)  Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.,  18  (6): [PMID:20185316] [10.1016/j.bmc.2010.01.068]

9. Forlani G, Giberti S, Berlicki L, Petrollino D, Kafarski P..  (2007)  Plant P5C reductase as a new target for aminomethylenebisphosphonates.,  55  (11): [PMID:17474756] [10.1021/jf0701032]

10. Wang K, Wang W, No JH, Zhang Y, Zhang Y, Oldfield E..  (2010)  Inhibition of the Fe(4)S(4)-cluster-containing protein IspH (LytB): electron paramagnetic resonance, metallacycles, and mechanisms.,  132  (19): [PMID:20426416] [10.1021/ja909664j]

Source

Source(1):

• Scientific Literature