Pentyl ((5R)-5-(((4-amino-5-fluoropyrimidin-2-yl)oxy)methyl)-2-oxido-1,4,2-dioxaphosphinan-2-yl)-L-valinate

ID: ALA4641987

PubChem CID: 156017091

Max Phase: Preclinical

Molecular Formula: C18H30FN4O6P

Molecular Weight: 448.43

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCCCOC(=O)[C@@H](NP1(=O)CO[C@H](COc2ncc(F)c(N)n2)CO1)C(C)C

Standard InChI:  InChI=1S/C18H30FN4O6P/c1-4-5-6-7-26-17(24)15(12(2)3)23-30(25)11-28-13(10-29-30)9-27-18-21-8-14(19)16(20)22-18/h8,12-13,15H,4-7,9-11H2,1-3H3,(H,23,25)(H2,20,21,22)/t13-,15+,30?/m1/s1

Standard InChI Key:  VYGWOVAYVUFJLS-GCJNNWJWSA-N

Molfile:  

 
     RDKit          2D

 30 31  0  0  0  0  0  0  0  0999 V2000
    3.8694  -21.7914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8682  -22.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5830  -23.0316    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2994  -22.6182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2966  -21.7877    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5812  -21.3786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5787  -20.5536    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0146  -23.0296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0159  -23.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7309  -24.2660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7282  -25.0877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4392  -25.4990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1555  -25.0889    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    8.1562  -24.2630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4406  -23.8471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8690  -25.5031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1499  -25.9121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5844  -25.0921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2979  -25.5062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0133  -25.0953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2961  -26.3312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7268  -25.5093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4422  -25.0984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1558  -25.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8711  -25.1016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5847  -25.5157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5862  -24.2671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3016  -23.8562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8727  -23.8531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1548  -21.3790    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  6  7  1  0
  4  8  1  0
  8  9  1  0
 10  9  1  1
 10 11  1  0
 10 15  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 13 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 18 27  1  1
 27 28  1  0
 27 29  1  0
  1 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4641987

   ---

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: 448.43

Molecular Weight (Monoisotopic): 448.1887

AlogP: 2.49

#Rotatable Bonds: 11

Polar Surface Area: 134.89

Molecular Species: NEUTRAL

HBA: 9

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.54

CX Basic pKa: 3.27

CX LogP: 2.23

CX LogD: 2.23

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.30

Np Likeness Score: -0.32

References

1. Luo M, Groaz E, Snoeck R, Andrei G, Herdewijn P..  (2020)  Amidate Prodrugs of O-2-Alkylated Pyrimidine Acyclic Nucleosides Display Potent Anti-Herpesvirus Activity.,  11  (7): [PMID:32676147] [10.1021/acsmedchemlett.0c00090]

Source

Source(1):

• Scientific Literature