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

ID: ALA4792121

PubChem CID: 153387978

Max Phase: Preclinical

Molecular Formula: C22H28NO5P

Molecular Weight: 417.44

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C22H28NO5P/c1-18(16-24)10-9-15-29(26,28-21-13-7-4-8-14-21)23-19(2)22(25)27-17-20-11-5-3-6-12-20/h3-8,10-14,19,24H,9,15-17H2,1-2H3,(H,23,26)/b18-10+/t19-,29?/m0/s1

Standard InChI Key:  ZSPCSEYMHKSWNW-OZRVKTBRSA-N

Molfile:  

 
     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
   27.7642   -3.0270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4725   -3.4420    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   28.6492   -2.6403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.1397   -5.6070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1025   -4.1817    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.5332   -4.8801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3452   -4.8564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3062   -5.6284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.5598   -6.2911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.2212   -3.8199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.8966   -3.3776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6365   -3.7891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3341   -3.3584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3078   -2.5400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5838   -2.1522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8881   -2.5793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3599   -6.2684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0539   -3.4310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3488   -3.0179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6385   -3.4219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9334   -3.0088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6332   -4.2391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2231   -3.4128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.7884   -6.9643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3960   -7.6804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8238   -8.3758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6415   -8.3530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0296   -7.6291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5995   -6.9367    0.0000 C   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
M  END

Alternative Forms

1. Parent:

   

   ALA4792121

   ---

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: 417.44

Molecular Weight (Monoisotopic): 417.1705

AlogP: 4.31

#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: 11.64

CX Basic pKa: ┄

CX LogP: 3.14

CX LogD: 3.14

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.32

Np Likeness Score: 0.50

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