1-hydroxy-2-(4-dimethylaminopyridinium-1-yl)-ethylidene-1,1-biphosphonic acid

ID: ALA202390

PubChem CID: 11508127

Max Phase: Preclinical

Molecular Formula: C9H17N2O7P2+

Molecular Weight: 327.19

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)c1cc[n+](CC(O)(P(=O)(O)O)P(=O)(O)O)cc1

Standard InChI:  InChI=1S/C9H16N2O7P2/c1-10(2)8-3-5-11(6-4-8)7-9(12,19(13,14)15)20(16,17)18/h3-6,12H,7H2,1-2H3,(H3-,13,14,15,16,17,18)/p+1

Standard InChI Key:  PDJZXGLGJUXHQW-UHFFFAOYSA-O

Molfile:  

     RDKit          2D

 20 20  0  0  0  0  0  0  0  0999 V2000
   13.8094   -3.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5243   -4.1180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2352   -4.5264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9341   -3.4034    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   14.1180   -4.8346    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   15.3392   -2.6876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6499   -3.8112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2190   -2.9947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7000   -5.5458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8314   -5.2464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4051   -4.4217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0094   -3.9190    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4286   -3.3286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6292   -3.5382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4106   -4.3369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9976   -4.9258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7947   -4.7130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6142   -4.5473    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0338   -3.9628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3982   -5.3423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  5 11  1  0
  4  6  2  0
  1 12  1  0
  1  2  1  0
 12 13  2  0
  4  7  1  0
 13 14  1  0
  2  4  1  0
 14 15  2  0
  4  8  1  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
  5  9  2  0
 15 18  1  0
  2  5  1  0
 18 19  1  0
  5 10  1  0
 18 20  1  0
M  CHG  1  12   1
M  END

Alternative Forms

1. Parent:

   

   ALA202390

   [2-[4-(Dimethylamino)pyridin-1-ium-1-yl]-1-hydroxy-1-phosphonoethyl]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: 327.19

Molecular Weight (Monoisotopic): 327.0506

AlogP: -0.96

#Rotatable Bonds: 5

Polar Surface Area: 142.41

Molecular Species: ACID

HBA: 4

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 0.60

CX Basic pKa: ┄

CX LogP: -5.62

CX LogD: -9.41

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.34

Np Likeness Score: -0.08

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