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

ID: ALA4790695

PubChem CID: 162670927

Max Phase: Preclinical

Molecular Formula: C19H30NO5P

Molecular Weight: 383.43

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C19H30NO5P/c1-15(14-21)10-9-13-26(23,25-17-11-7-6-8-12-17)20-16(2)18(22)24-19(3,4)5/h6-8,10-12,16,21H,9,13-14H2,1-5H3,(H,20,23)/b15-10+/t16-,26?/m0/s1

Standard InChI Key:  OCVWINQMYJFMGU-GWKDSOCRSA-N

Molfile:  

 
     RDKit          2D

 26 26  0  0  0  0  0  0  0  0999 V2000
   21.6597   -5.1673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4492   -5.9597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2407   -5.7458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8564   -2.7216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5648   -3.1366    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   20.7414   -2.3349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2319   -5.3016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1948   -3.8763    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.6254   -4.5747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4374   -4.5510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3984   -5.3229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6520   -5.9857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3134   -3.5145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9889   -3.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7288   -3.4837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4264   -3.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4000   -2.2346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6761   -1.8468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9804   -2.2739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1461   -3.1256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4411   -2.7124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7307   -3.1165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0257   -2.7033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7255   -3.9337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3153   -3.1074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8807   -6.6589    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
  2 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4790695

   ---

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: 383.43

Molecular Weight (Monoisotopic): 383.1862

AlogP: 3.91

#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: 11.64

CX Basic pKa: ┄

CX LogP: 2.33

CX LogD: 2.33

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.38

Np Likeness Score: 0.65

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