(2-(1-(3,7-Dimethyl-octa-2,6-dieny1)-1H-[1,2,3]triazol-4-y1l)1-1-fluoro-1-phosphono-ethyl)-phosphonic acid

ID: ALA4877993

PubChem CID: 164629185

Max Phase: Preclinical

Molecular Formula: C14H20FN3Na4O6P2

Molecular Weight: 411.31

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C14H24FN3O6P2.4Na/c1-11(2)5-4-6-12(3)7-8-18-10-13(16-17-18)9-14(15,25(19,20)21)26(22,23)24;;;;/h5,7,10H,4,6,8-9H2,1-3H3,(H2,19,20,21)(H2,22,23,24);;;;/q;4*+1/p-4/b12-7+;;;;

Standard InChI Key:  IEWDCYQUCJGZKM-BLSNBFPRSA-J

Molfile:  

     RDKit          2D

 30 26  0  0  0  0  0  0  0  0999 V2000
    9.6251  -14.8418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0417  -15.5585    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   10.4540  -14.8392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3293  -15.9751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0464  -16.3838    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.2751  -17.1376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9918  -16.7292    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    8.2797  -16.3128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0253  -15.3948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0042  -15.1209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7187  -14.7084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4331  -15.1209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7187  -13.8834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1476  -14.7084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8621  -15.1209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5765  -14.7084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2910  -15.1209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5765  -13.8834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0055  -14.7084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7199  -15.1209    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8059  -15.9378    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6128  -16.1093    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4732  -14.7818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8458  -15.3085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4803  -17.3970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7585  -15.9669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1125  -18.6126    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
   10.0251  -18.2709    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
   12.1709  -16.6126    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
   12.9501  -15.3959    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  2  1  0
  5  4  1  0
  7  6  1  0
  8  7  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22  9  1  0
  9 23  2  0
 23 20  1  0
  9 24  1  0
 24  4  1  0
  4  7  1  0
  7 25  1  0
  2 26  1  0
M  CHG  8   3  -1   6  -1  25  -1  26  -1  27   1  28   1  29   1  30   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: 411.31

Molecular Weight (Monoisotopic): 411.1124

AlogP: 2.49

#Rotatable Bonds: 9

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: 0.74

CX Basic pKa: 0.14

CX LogP: 0.75

CX LogD: -3.65

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.36

Np Likeness Score: 0.26

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