tert-Butyl (((E)-1,1-difluoro-5-hydroxy-4-methylpent-3-en-1-yl)-(phenoxy)phosphoryl)-L-alaninate

ID: ALA4793602

PubChem CID: 162674037

Max Phase: Preclinical

Molecular Formula: C19H28F2NO5P

Molecular Weight: 419.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C/C(=C\CC(F)(F)P(=O)(N[C@@H](C)C(=O)OC(C)(C)C)Oc1ccccc1)CO

Standard InChI:  InChI=1S/C19H28F2NO5P/c1-14(13-23)11-12-19(20,21)28(25,27-16-9-7-6-8-10-16)22-15(2)17(24)26-18(3,4)5/h6-11,15,23H,12-13H2,1-5H3,(H,22,25)/b14-11+/t15-,28?/m0/s1

Standard InChI Key:  SVNXVFMFYNGNIB-BRUKFHTCSA-N

Molfile:  

 
     RDKit          2D

 28 28  0  0  0  0  0  0  0  0999 V2000
   21.1190  -13.9913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4133  -13.5827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4123  -14.3982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8202  -10.3428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5285  -10.7579    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   19.7051   -9.9561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1957  -12.9229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1585  -11.4976    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.5891  -12.1959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4011  -12.1723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3622  -12.9442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6157  -13.6070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2772  -11.1358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9526  -10.6935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6925  -11.1050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3901  -10.6743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3637   -9.8558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6398   -9.4681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9441   -9.8951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1098  -10.7469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4048  -10.3337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6945  -10.7378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9894  -10.3246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6892  -11.5549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2791  -10.7287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4074   -9.6330    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   19.2286   -9.6305    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   20.8043  -12.8653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  5  4  1  0
  6  5  2  0
  8  9  1  0
  7  9  1  0
  9 10  1  1
  7 11  2  0
  7 12  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 14 19  2  0
 13 14  1  0
  5 13  1  0
  8  5  1  0
 12  2  1  0
  4 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 23 25  1  0
  4 26  1  0
 27  4  1  0
  2 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4793602

   ---

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: 419.41

Molecular Weight (Monoisotopic): 419.1673

AlogP: 4.50

#Rotatable Bonds: 9

Polar Surface Area: 84.86

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.89

CX Basic pKa: ┄

CX LogP: 2.95

CX LogD: 2.95

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.35

Np Likeness Score: 0.35

References

1. Kadri H,Taher TE,Xu Q,Sharif M,Ashby E,Bryan RT,Willcox BE,Mehellou Y.  (2020)  Aryloxy Diester Phosphonamidate Prodrugs of Phosphoantigens (ProPAgens) as Potent Activators of Vγ9/Vδ2 T-Cell Immune Responses.,  63  (19.0): [PMID:32930595] [10.1021/acs.jmedchem.0c01232]

Source

Source(1):

• Scientific Literature