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

ID: ALA4754419

PubChem CID: 162654092

Max Phase: Preclinical

Molecular Formula: C22H26F2NO5P

Molecular Weight: 453.42

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C/C(=C\CC(F)(F)P(=O)(N[C@@H](C)C(=O)OCc1ccccc1)Oc1ccccc1)CO

Standard InChI:  InChI=1S/C22H26F2NO5P/c1-17(15-26)13-14-22(23,24)31(28,30-20-11-7-4-8-12-20)25-18(2)21(27)29-16-19-9-5-3-6-10-19/h3-13,18,26H,14-16H2,1-2H3,(H,25,28)/b17-13+/t18-,31?/m0/s1

Standard InChI Key:  HUMLAWKATWWMJP-UUUALGSWSA-N

Molfile:  

 
     RDKit          2D

 31 32  0  0  0  0  0  0  0  0999 V2000
   27.0816  -10.4744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7966  -10.8933    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   27.9749  -10.0840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.4606  -13.0788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4231  -11.6400    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.8578  -12.3450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6776  -12.3211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6192  -13.1003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.8846  -13.7694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.5524  -11.2748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.2342  -10.8283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9811  -11.2437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6853  -10.8089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6588   -9.9827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9279   -9.5913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2256  -10.0224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6924  -13.7465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3645  -10.8822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6527  -10.4651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9357  -10.8730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2239  -10.4559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9304  -11.6980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5069  -10.8638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.1250  -14.4490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7288  -15.1719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1606  -15.8739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9862  -15.8509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3779  -15.1201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9438  -14.4212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6650   -9.7577    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   27.4938   -9.7552    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  2  0
  5  6  1  0
  4  6  1  0
  6  7  1  1
  4  8  2  0
  4  9  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 11 16  2  0
 10 11  1  0
  2 10  1  0
  5  2  1  0
  9 17  1  0
  1 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 21 23  1  0
 17 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
  1 30  1  0
 31  1  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4754419

   ---

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: 453.42

Molecular Weight (Monoisotopic): 453.1517

AlogP: 4.90

#Rotatable Bonds: 11

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: 3.76

CX LogD: 3.76

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.29

Np Likeness Score: 0.24

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