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

ID: ALA4743632

PubChem CID: 153387980

Max Phase: Preclinical

Molecular Formula: C16H24NO5P

Molecular Weight: 341.34

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC(=O)[C@H](C)NP(=O)(CC/C=C(\C)CO)Oc1ccccc1

Standard InChI:  InChI=1S/C16H24NO5P/c1-13(12-18)8-7-11-23(20,17-14(2)16(19)21-3)22-15-9-5-4-6-10-15/h4-6,8-10,14,18H,7,11-12H2,1-3H3,(H,17,20)/b13-8+/t14-,23?/m0/s1

Standard InChI Key:  DZZKNRBNLOBURN-JVMCCQDESA-N

Molfile:  

 
     RDKit          2D

 23 23  0  0  0  0  0  0  0  0999 V2000
    4.2101   -2.4038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9185   -2.8188    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    5.0951   -2.0171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5856   -4.9838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5484   -3.5585    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9791   -4.2569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7911   -4.2332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7521   -5.0052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0057   -5.6679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6671   -3.1967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3425   -2.7544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0824   -3.1659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7800   -2.7352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7537   -1.9168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0297   -1.5290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3340   -1.9561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8058   -5.6452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4998   -2.8078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7947   -2.3947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0844   -2.7987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3793   -2.3855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0792   -3.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6690   -2.7896    0.0000 O   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
M  END

Alternative Forms

1. Parent:

   

   ALA4743632

   ---

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: 341.34

Molecular Weight (Monoisotopic): 341.1392

AlogP: 2.74

#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: 1.42

CX LogD: 1.42

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.41

Np Likeness Score: 0.76

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