2-[3-(3,7-Dimethyl-octyloxy)-pyridinium-1-yl]ethylidene-1,1-bisphosphonic acid

ID: ALA494279

PubChem CID: 25023874

Max Phase: Preclinical

Molecular Formula: C17H31NO7P2

Molecular Weight: 423.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)CCCC(C)CCOc1ccc[n+](CC(P(=O)([O-])O)P(=O)(O)O)c1

Standard InChI:  InChI=1S/C17H31NO7P2/c1-14(2)6-4-7-15(3)9-11-25-16-8-5-10-18(12-16)13-17(26(19,20)21)27(22,23)24/h5,8,10,12,14-15,17H,4,6-7,9,11,13H2,1-3H3,(H3-,19,20,21,22,23,24)

Standard InChI Key:  WHQLUYYDOZYPJB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 27  0  0  0  0  0  0  0  0999 V2000
    4.3641   -2.6527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0797   -3.0666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0790   -3.8933    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    5.7960   -2.6539    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    6.5132   -2.2354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2107   -3.3691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3782   -1.9405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0773   -4.7133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9057   -3.8946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2523   -3.8988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6478   -3.0653    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9364   -2.6477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2206   -3.0597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2194   -3.8872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9401   -4.3011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6530   -3.8866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5052   -2.6454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7908   -3.0533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0791   -2.6413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6364   -3.0520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3483   -2.6400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0638   -3.0507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7755   -2.6387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4910   -3.0494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2029   -2.6374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4925   -3.8761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6379   -3.8787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  2  0
  2  4  1  0
 14 15  1  0
  3  8  1  0
 15 16  2  0
 16 11  1  0
 13 17  1  0
  3  9  1  0
 17 18  1  0
  4  5  1  0
 18 19  1  0
  3 10  2  0
 19 20  1  0
  2  3  1  0
 20 21  1  0
  1 11  1  0
 21 22  1  0
  4  6  1  0
 22 23  1  0
 11 12  2  0
 23 24  1  0
  1  2  1  0
 24 25  1  0
 12 13  1  0
 24 26  1  0
  4  7  2  0
 20 27  1  0
M  CHG  2   5  -1  11   1
M  END

Alternative Forms

1. Parent:

   

   ALA494279

   Bisphosphonate, 24

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: 423.38

Molecular Weight (Monoisotopic): 423.1576

AlogP: 2.25

#Rotatable Bonds: 12

Polar Surface Area: 131.00

Molecular Species: ACID

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.11

CX Basic pKa: ┄

CX LogP: -2.25

CX LogD: -5.82

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.35

Np Likeness Score: 0.31

References

1. 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]

2. 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