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

ID: ALA4876427

PubChem CID: 164626819

Max Phase: Preclinical

Molecular Formula: C16H25N3Na4O6P2

Molecular Weight: 421.37

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCC(Cc1cn(C/C=C(\C)CCC=C(C)C)nn1)(P(=O)([O-])[O-])P(=O)([O-])[O-].[Na+].[Na+].[Na+].[Na+]

Standard InChI:  InChI=1S/C16H29N3O6P2.4Na/c1-5-16(26(20,21)22,27(23,24)25)11-15-12-19(18-17-15)10-9-14(4)8-6-7-13(2)3;;;;/h7,9,12H,5-6,8,10-11H2,1-4H3,(H2,20,21,22)(H2,23,24,25);;;;/q;4*+1/p-4/b14-9+;;;;

Standard InChI Key:  SUBVZNRGWUCDKV-GPZOHOMCSA-J

Molfile:  

     RDKit          2D

 31 27  0  0  0  0  0  0  0  0999 V2000
   21.8918   -5.8542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3085   -6.5708    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   22.7208   -5.8517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5959   -6.9876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3130   -7.3963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5418   -8.1501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2584   -7.7417    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   20.5465   -7.3252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2921   -6.4073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2709   -6.1334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9854   -5.7209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6998   -6.1334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9854   -4.8959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4143   -5.7209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1289   -6.1334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8433   -5.7209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5578   -6.1334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8433   -4.8959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2723   -5.7209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9867   -6.1334    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.0725   -6.9502    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.8796   -7.1218    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.7400   -5.7943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1126   -6.3210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7471   -8.4094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0253   -6.9794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3177   -8.2213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3793   -9.6251    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
   22.2918   -9.2834    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
   24.4377   -7.6250    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
   25.2168   -6.4084    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
  5 27  1  0
M  CHG  8   3  -1   6  -1  25  -1  26  -1  28   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: 421.37

Molecular Weight (Monoisotopic): 421.1532

AlogP: 2.98

#Rotatable Bonds: 10

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: 1.21

CX Basic pKa: 0.31

CX LogP: 1.51

CX LogD: -2.91

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.33

Np Likeness Score: 0.36

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