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

ID: ALA4759010

PubChem CID: 162658240

Max Phase: Preclinical

Molecular Formula: C15H23N3Na4O7P2

Molecular Weight: 423.34

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)=CCC/C(C)=C/CCc1cn(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/b13-8+;;;;

Standard InChI Key:  NORWCZMTXKXQSP-MEVDHSCASA-J

Molfile:  

     RDKit          2D

 31 27  0  0  0  0  0  0  0  0999 V2000
    9.0949  -10.2368    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
    7.7391   -8.3408    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6963  -10.0578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6792  -10.1949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2247   -6.2619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5542   -9.6449    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    7.0776   -7.1815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9916   -8.0028    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4625   -8.5074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9750  -10.4740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2750   -8.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5501  -10.4698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9791   -9.6491    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    7.6917   -9.2324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8854   -7.0139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7423   -9.3493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2709   -9.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2942   -7.7305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7477   -5.5984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0838   -4.8535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8969   -4.7721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3739   -5.4356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2330   -4.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0461   -3.9458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3822   -3.2010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1953   -3.1196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6724   -3.7831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5314   -2.3747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8042   -9.1616    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
    3.3085   -8.9450    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
    3.3415  -10.3936    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  0
 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