sodium (E/Z)-2-(4-(4,8-dimethylnona-3,7-dienyl)-1H-1,2,3-triazol-1-yl)-1-hydroxyethane-1,1-diyldiphosphonate

ID: ALA4740510

PubChem CID: 162644871

Max Phase: Preclinical

Molecular Formula: C15H23N3Na4O7P2

Molecular Weight: 423.34

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)=CCCC(C)=CCCc1cn(CC(O)(P(=O)([O-])[O-])P(=O)([O-])[O-])nn1.[Na+].[Na+].[Na+].[Na+]

Standard InChI:  InChI=1S/C15H27N3O7P2.4Na/c1-12(2)6-4-7-13(3)8-5-9-14-10-18(17-16-14)11-15(19,26(20,21)22)27(23,24)25;;;;/h6,8,10,19H,4-5,7,9,11H2,1-3H3,(H2,20,21,22)(H2,23,24,25);;;;/q;4*+1/p-4

Standard InChI Key:  NORWCZMTXKXQSP-UHFFFAOYSA-J

Molfile:  

     RDKit          2D

 31 27  0  0  0  0  0  0  0  0999 V2000
   15.2168  -12.6256    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
   13.7454   -9.2022    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7002  -10.9360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6545  -11.0722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2355   -7.1024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5407  -10.5162    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   13.0759   -8.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9891   -8.8605    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4450   -9.3715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9719  -11.3566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2681   -9.2738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5342  -11.3501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9783  -10.5228    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   13.6974  -10.1014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8917   -7.8614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7184  -10.2190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2618  -10.1079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3051   -8.5867    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7545   -6.4341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0932   -5.6818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9131   -5.5980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2519   -4.8459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3942   -6.2664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2139   -6.1869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6950   -6.8552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5191   -6.7758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8579   -6.0236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0001   -7.4442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0854  -11.0561    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
    9.1642  -10.1632    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
    9.1300  -11.9886    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
 15  5  1  0
  8  2  1  0
 13 10  2  0
 17  9  1  0
 15  7  2  0
 18 15  1  0
 16  6  1  0
  2 18  2  0
  3 13  1  0
 17  6  1  0
 17 13  1  0
 13 14  1  0
 11 17  1  0
  6  4  1  0
 11  8  1  0
  7  8  1  0
  6 12  2  0
  5 19  1  0
 19 20  1  0
 20 21  2  3
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26 28  1  0
M  CHG  8   1   1   3  -1   4  -1  14  -1  16  -1  29   1  30   1  31   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: 423.34

Molecular Weight (Monoisotopic): 423.1324

AlogP: 1.90

#Rotatable Bonds: 10

Polar Surface Area: 166.00

Molecular Species: ACID

HBA: 6

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 0.86

CX Basic pKa: 0.30

CX LogP: 0.15

CX LogD: -4.07

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.28

Np Likeness Score: 0.55

References

1. Legigan T,Migianu-Griffoni E,Redouane MA,Descamps A,Deschamp J,Gager O,Monteil M,Barbault F,Lecouvey M.  (2021)  Synthesis and preliminary anticancer evaluation of new triazole bisphosphonate-based isoprenoid biosynthesis inhibitors.,  214  [PMID:33571830] [10.1016/j.ejmech.2021.113241]

Source

Source(1):

• Scientific Literature