sodium 1-(1-(9-hydroxy-4,8-dimethylnona-3,7-dienyl)-1H-1,2,3-triazol-4-yl)propane-2,2-diyldiphosphonate

ID: ALA4476604

PubChem CID: 155538427

Max Phase: Preclinical

Molecular Formula: C16H25N3Na4O7P2

Molecular Weight: 437.37

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C/C(=C/CCn1cc(CC(C)(P(=O)([O-])[O-])P(=O)([O-])[O-])nn1)CC/C=C(\C)CO.[Na+].[Na+].[Na+].[Na+]

Standard InChI:  InChI=1S/C16H29N3O7P2.4Na/c1-13(6-4-7-14(2)12-20)8-5-9-19-11-15(17-18-19)10-16(3,27(21,22)23)28(24,25)26;;;;/h7-8,11,20H,4-6,9-10,12H2,1-3H3,(H2,21,22,23)(H2,24,25,26);;;;/q;4*+1/p-4/b13-8-,14-7+;;;;

Standard InChI Key:  CMTDJZGPYKTRIM-NSCZPZIUSA-J

Molfile:  

     RDKit          2D

 32 28  0  0  0  0  0  0  0  0999 V2000
    5.1125  -15.3035    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
    6.1619  -13.3310    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9791  -13.3310    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2335  -12.5543    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5705  -12.0721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9118  -12.5543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1345  -12.3021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5274  -12.8492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7501  -12.5970    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.6977  -13.6484    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    3.5799  -11.7977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1431  -13.1441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7434  -13.4135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0906  -14.1955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4750  -13.9006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6927  -14.4618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0110  -12.3028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3117  -13.0586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1820  -11.5037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9596  -11.2523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1306  -10.4532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9081  -10.2017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5241   -9.9055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6951   -9.1064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4726   -8.8550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6436   -8.0559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4212   -7.8044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0371   -7.5082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0277   -8.3521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836  -13.3949    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
    3.2720  -13.7698    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
    3.4765  -14.8945    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  2  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
  9 11  2  0
  9 12  1  0
  9 13  1  0
 10 14  1  0
 10 15  2  0
 10 16  1  0
  4 17  1  0
  8 18  1  0
 17 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
 27 29  1  0
M  CHG  8   1   1  12  -1  13  -1  14  -1  16  -1  30   1  31   1  32   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: 437.37

Molecular Weight (Monoisotopic): 437.1481

AlogP: 1.95

#Rotatable Bonds: 11

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: 1.20

CX Basic pKa: 0.25

CX LogP: -0.06

CX LogD: -4.49

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.26

Np Likeness Score: 0.41

References

1. Bhuiyan NH, Varney ML, Bhattacharya DS, Payne WM, Mohs AM, Holstein SA, Wiemer DF..  (2019)  ω-Hydroxy isoprenoid bisphosphonates as linkable GGDPS inhibitors.,  29  (19): [PMID:31474482] [10.1016/j.bmcl.2019.126633]

Source

Source(1):

• Scientific Literature