sodium (E)-2-(1-(3,7-dimethylocta-2,6-dienyl)-1H-1,2,3-triazol-4-yl)ethene-1,1-diyldiphosphonate

ID: ALA4856822

PubChem CID: 164613573

Max Phase: Preclinical

Molecular Formula: C14H19N3Na4O6P2

Molecular Weight: 391.30

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C14H23N3O6P2.4Na/c1-11(2)5-4-6-12(3)7-8-17-10-13(15-16-17)9-14(24(18,19)20)25(21,22)23;;;;/h5,7,9-10H,4,6,8H2,1-3H3,(H2,18,19,20)(H2,21,22,23);;;;/q;4*+1/p-4/b12-7+;;;;

Standard InChI Key:  FNVFNANSBQZIKF-BLSNBFPRSA-J

Molfile:  

     RDKit          2D

 29 25  0  0  0  0  0  0  0  0999 V2000
   11.5793  -27.2960    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
    9.0500  -26.0626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7667  -25.6543    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    9.0548  -25.2378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9209  -23.9877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9251  -24.8126    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   11.6374  -24.3966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8004  -24.3198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7792  -24.0459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4936  -23.6334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2081  -24.0459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4936  -22.8084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9227  -23.6334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6371  -24.0459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3516  -23.6334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0661  -24.0459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3516  -22.8084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7805  -23.6334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4950  -24.0459    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5808  -24.8629    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3878  -25.0344    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2482  -23.7068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6208  -24.2335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1058  -24.9009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4113  -25.4820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2553  -26.3221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4584  -27.2918    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
   12.0792  -25.7543    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
   12.8584  -24.5376    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
  3  2  1  0
  4  3  2  0
  6  5  2  0
  7  6  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21  8  1  0
  8 22  2  0
 22 19  1  0
  8 23  1  0
 23 24  2  0
 24  6  1  0
 24  3  1  0
  6 25  1  0
  3 26  1  0
M  CHG  8   1   1   2  -1   7  -1  25  -1  26  -1  27   1  28   1  29   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: 391.30

Molecular Weight (Monoisotopic): 391.1062

AlogP: 2.62

#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: 1.47

CX Basic pKa: ┄

CX LogP: 1.34

CX LogD: -3.62

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.39

Np Likeness Score: 0.51

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