hydrogen 2-[3-(1,1'-biphenyl-3-yl)pyridinium-1-yl]-1-hydroxy-1-phosphonoethylphosphonate

ID: ALA192017

PubChem CID: 11305096

Max Phase: Preclinical

Molecular Formula: C19H19NO7P2

Molecular Weight: 435.31

Molecule Type: Small molecule

Names and Identifiers

Synonyms: BPH-364 | CHEMBL192017|bisphosphonate, 7|BDBM25297|BPH-364|1-(2-hydrogen phosphonato-2-hydroxy-2-phosphonoethyl)-3-(3-phenylphenyl)pyridin-1-ium

Canonical SMILES:  O=P([O-])(O)C(O)(C[n+]1cccc(-c2cccc(-c3ccccc3)c2)c1)P(=O)(O)O

Standard InChI:  InChI=1S/C19H19NO7P2/c21-19(28(22,23)24,29(25,26)27)14-20-11-5-10-18(13-20)17-9-4-8-16(12-17)15-6-2-1-3-7-15/h1-13,21H,14H2,(H3-,22,23,24,25,26,27)

Standard InChI Key:  SFGYQDTXSJEVCC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
    2.5189    1.0891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2354    0.6714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9031   -0.0868    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    3.5529    1.4413    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    3.8618    2.2133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3207    1.1316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7837    1.7475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5726   -0.8387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6612   -0.4196    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1424    0.2440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8049    0.6735    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9497    0.2622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0884    1.0855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3749    0.6705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3773   -0.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0993   -0.5669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8099   -0.1495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3374    1.0788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3385    1.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0526    2.3138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7660    1.8995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0462    0.6651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7586    1.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4664    0.6482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1843    1.0550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8935    0.6369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8860   -0.1881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1634   -0.5930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4572   -0.1725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  2  0
  3  8  1  0
 15 16  1  0
 16 17  2  0
 17 11  1  0
  3  9  1  0
  4  5  1  0
 18 19  2  0
  3 10  2  0
 19 20  1  0
  2  3  1  0
 20 21  2  0
 21 23  1  0
 22 18  1  0
 14 18  1  0
 22 23  2  0
  1 11  1  0
  4  6  1  0
  2 12  1  0
  1  2  1  0
 24 25  2  0
 11 13  2  0
 25 26  1  0
  4  7  2  0
 26 27  2  0
 13 14  1  0
 27 28  1  0
  2  4  1  0
 28 29  2  0
 29 24  1  0
 23 24  1  0
M  CHG  2   5  -1  11   1
M  END

Alternative Forms

1. Parent:

   

   ALA192017

   Bisphosphonate, 7

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: 435.31

Molecular Weight (Monoisotopic): 435.0637

AlogP: 1.68

#Rotatable Bonds: 6

Polar Surface Area: 142.00

Molecular Species: ACID

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 0.59

CX Basic pKa: ┄

CX LogP: -2.51

CX LogD: -6.30

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.34

Np Likeness Score: 0.03

References

1. Sanders JM, Song Y, Chan JM, Zhang Y, Jennings S, Kosztowski T, Odeh S, Flessner R, Schwerdtfeger C, Kotsikorou E, Meints GA, Gómez AO, González-Pacanowska D, Raker AM, Wang H, van Beek ER, Papapoulos SE, Morita CT, Oldfield E..  (2005)  Pyridinium-1-yl bisphosphonates are potent inhibitors of farnesyl diphosphate synthase and bone resorption.,  48  (8): [PMID:15828834] [10.1021/jm040209d]

2. Zhang Y, Leon A, Song Y, Studer D, Haase C, Koscielski LA, Oldfield E..  (2006)  Activity of nitrogen-containing and non-nitrogen-containing bisphosphonates on tumor cell lines.,  49  (19): [PMID:16970405] [10.1021/jm060280e]

3. Guo RT, Cao R, Liang PH, Ko TP, Chang TH, Hudock MP, Jeng WY, Chen CK, Zhang Y, Song Y, Kuo CJ, Yin F, Oldfield E, Wang AH..  (2007)  Bisphosphonates target multiple sites in both cis- and trans-prenyltransferases.,  104  (24): [PMID:17535895] [10.1073/pnas.0702254104]

4. K-M Chen C, Hudock MP, Zhang Y, Guo RT, Cao R, No JH, Liang PH, Ko TP, Chang TH, Chang SC, Song Y, Axelson J, Kumar A, Wang AH, Oldfield E..  (2008)  Inhibition of geranylgeranyl diphosphate synthase by bisphosphonates: a crystallographic and computational investigation.,  51  (18): [PMID:18800762] [10.1021/jm800325y]

5. Malwal SR, Chen L, Hicks H, Qu F, Liu W, Shillo A, Law WX, Zhang J, Chandnani N, Han X, Zheng Y, Chen CC, Guo RT, AbdelKhalek A, Seleem MN, Oldfield E..  (2019)  Discovery of Lipophilic Bisphosphonates That Target Bacterial Cell Wall and Quinone Biosynthesis.,  62  (5): [PMID:30730737] [10.1021/acs.jmedchem.8b01878]

Source

Source(1):

• Scientific Literature