disodium mono((E)-2-(1-(3,7-dimethylocta-2,6-dienyl)-1H-1,2,3-triazol-4-yl)cyclopropane-1,1-diyldiphosphonate)

ID: ALA4874626

PubChem CID: 164628836

Max Phase: Preclinical

Molecular Formula: C15H23N3Na2O6P2

Molecular Weight: 405.33

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)=CCC/C(C)=C/Cn1cc(C2CC2(P(=O)([O-])[O-])P(=O)(O)O)nn1.[Na+].[Na+]

Standard InChI:  InChI=1S/C15H25N3O6P2.2Na/c1-11(2)5-4-6-12(3)7-8-18-10-14(16-17-18)13-9-15(13,25(19,20)21)26(22,23)24;;/h5,7,10,13H,4,6,8-9H2,1-3H3,(H2,19,20,21)(H2,22,23,24);;/q;2*+1/p-2/b12-7+;;

Standard InChI Key:  VLMHUNLXKCMFJF-CURPJKDSSA-L

Molfile:  

     RDKit          2D

 28 27  0  0  0  0  0  0  0  0999 V2000
   26.6877  -26.2877    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
   24.9252  -25.8419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5168  -26.5585    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   25.3416  -26.5538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.5004  -25.5656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4793  -25.2918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1938  -24.8793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9082  -25.2918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1938  -24.0543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6227  -24.8793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3372  -25.2918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0516  -24.8793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7661  -25.2918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0516  -24.0543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4806  -24.8793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1950  -25.2918    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.2810  -26.1087    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.0879  -26.2802    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.9483  -24.9527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7502  -27.3085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4669  -26.9002    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   22.7548  -26.4836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.9429  -27.5054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3183  -25.4757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8059  -26.1467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1433  -25.3890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5157  -27.3835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.2210  -24.8210    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
  3  2  1  0
  4  3  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18  5  1  0
  5 19  2  0
 19 16  1  0
  5 24  1  0
 21 20  1  0
 22 21  2  0
 25 21  1  0
 21 23  1  0
 25 24  1  0
 26 25  1  0
 24 26  1  0
 25  3  1  0
  3 27  2  0
M  CHG  4   1   1   2  -1   4  -1  28   1
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 405.33

Molecular Weight (Monoisotopic): 405.1219

AlogP: 2.51

#Rotatable Bonds: 8

Polar Surface Area: 145.77

Molecular Species: ACID

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.20

CX Basic pKa: 0.26

CX LogP: 0.74

CX LogD: -3.69

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.38

Np Likeness Score: 0.69

References

1. Fairweather AER, Goetz DB, Schroeder CM, Bhuiyan NH, Varney ML, Wiemer DF, Holstein SA..  (2021)  Impact of α-modifications on the activity of triazole bisphosphonates as geranylgeranyl diphosphate synthase inhibitors.,  44  [PMID:34298413] [10.1016/j.bmc.2021.116307]

Source

Source(1):

• Scientific Literature