2-(pyridin-4-ylamino)ethylidene-1,1-biphosphonic acid

ID: ALA370377

PubChem CID: 11659398

Max Phase: Preclinical

Molecular Formula: C7H12N2O7P2

Molecular Weight: 298.13

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=P(O)(O)C(O)(CNc1ccncc1)P(=O)(O)O

Standard InChI:  InChI=1S/C7H12N2O7P2/c10-7(17(11,12)13,18(14,15)16)5-9-6-1-3-8-4-2-6/h1-4,10H,5H2,(H,8,9)(H2,11,12,13)(H2,14,15,16)

Standard InChI Key:  AKTIZEIVLVIZDA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 18 18  0  0  0  0  0  0  0  0999 V2000
    6.2049  -10.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6387   -9.4371    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    5.8332  -10.8792    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    5.4533  -11.6086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5680  -11.2559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0967  -10.5057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0670   -8.7311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3441   -9.8665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9334   -9.0075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9193  -10.5558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4891   -9.7301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7746  -10.1442    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0587   -9.7325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0608   -8.9079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3458   -8.4963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6303   -8.9105    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6343   -9.7405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3499  -10.1484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  5  1  0
  1 10  1  0
  1  3  1  0
  1 11  1  0
  3  6  1  0
 11 12  1  0
  1  2  1  0
 12 13  1  0
  2  7  2  0
 13 14  2  0
  3  4  2  0
 14 15  1  0
  2  8  1  0
 15 16  2  0
 16 17  1  0
  2  9  1  0
 17 18  2  0
 18 13  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA370377

   [1-Hydroxy-1-phosphono-2-(pyridin-4-ylamino)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: 298.13

Molecular Weight (Monoisotopic): 298.0120

AlogP: -0.51

#Rotatable Bonds: 5

Polar Surface Area: 160.21

Molecular Species: ZWITTERION

HBA: 5

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 0.66

CX Basic pKa: 8.90

CX LogP: -3.85

CX LogD: -7.07

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.39

Np Likeness Score: -0.36

References

1. Hudock MP, Sanz-Rodríguez CE, Song Y, Chan JM, Zhang Y, Odeh S, Kosztowski T, Leon-Rossell A, Concepción JL, Yardley V, Croft SL, Urbina JA, Oldfield E..  (2006)  Inhibition of Trypanosoma cruzi hexokinase by bisphosphonates.,  49  (1): [PMID:16392806] [10.1021/jm0582625]

Source

Source(1):

• Scientific Literature