[2-(3-Methyl-pyridin-2-ylamino)-1-phosphono-ethyl]-phosphonic acid

ID: ALA98719

PubChem CID: 10424622

Max Phase: Preclinical

Molecular Formula: C8H14N2O6P2

Molecular Weight: 296.16

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cccnc1NCC(P(=O)(O)O)P(=O)(O)O

Standard InChI:  InChI=1S/C8H14N2O6P2/c1-6-3-2-4-9-8(6)10-5-7(17(11,12)13)18(14,15)16/h2-4,7H,5H2,1H3,(H,9,10)(H2,11,12,13)(H2,14,15,16)

Standard InChI Key:  MEVVOZVAMXABEA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 18 18  0  0  0  0  0  0  0  0999 V2000
   11.4375  -14.0468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4362  -14.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1492  -15.2871    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8684  -14.8738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8652  -14.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1472  -13.6340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5833  -15.2856    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2972  -14.8725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0120  -15.2843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7261  -14.8711    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   15.0128  -16.1092    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   15.0047  -16.9340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4346  -14.4501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1434  -15.5828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3095  -14.1592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8341  -16.1091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1842  -16.1046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5776  -13.6267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0
  4  5  1  0
  9 10  1  0
  2  3  1  0
  9 11  1  0
  5  6  2  0
 11 12  1  0
  6  1  1  0
 10 13  2  0
  1  2  2  0
 10 14  1  0
  4  7  1  0
 10 15  1  0
  3  4  2  0
 11 16  2  0
  7  8  1  0
 11 17  1  0
  5 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA98719

   [2-[(3-Methylpyridin-2-yl)amino]-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: 296.16

Molecular Weight (Monoisotopic): 296.0327

AlogP: 0.48

#Rotatable Bonds: 5

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: 1.18

CX Basic pKa: 7.04

CX LogP: -3.64

CX LogD: -5.84

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.49

Np Likeness Score: -0.64

References

1. 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+]

2. Dunford JE, Kwaasi AA, Rogers MJ, Barnett BL, Ebetino FH, Russell RG, Oppermann U, Kavanagh KL..  (2008)  Structure-activity relationships among the nitrogen containing bisphosphonates in clinical use and other analogues: time-dependent inhibition of human farnesyl pyrophosphate synthase.,  51  (7): [PMID:18327899] [10.1021/jm7015733]

3. Hounslow AM, Carran J, Brown RJ, Rejman D, Blackburn GM, Watts DJ..  (2008)  Determination of the microscopic equilibrium dissociation constants for risedronate and its analogues reveals two distinct roles for the nitrogen atom in nitrogen-containing bisphosphonate drugs.,  51  (14): [PMID:18590315] [10.1021/jm7015792]

Source

Source(1):

• Scientific Literature