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

ID: ALA4649652

PubChem CID: 156022189

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?/m0/s1

Standard InChI Key:  VYGWOVAYVUFJLS-IVQJTNLTSA-N

Molfile:  

 
     RDKit          2D

 30 31  0  0  0  0  0  0  0  0999 V2000
   18.9074  -12.9920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9063  -13.8194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6211  -14.2323    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.3376  -13.8189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3348  -12.9884    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.6194  -12.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6168  -11.7542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.0528  -14.2303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0540  -15.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7692  -15.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7664  -16.2885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4775  -16.6998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1938  -16.2898    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   23.1944  -15.4638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4788  -15.0479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.9074  -16.7039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.1881  -17.1130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.6228  -16.2929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3363  -16.7070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0517  -16.2961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.3345  -17.5320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.7653  -16.7101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4807  -16.2992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1943  -16.7133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9097  -16.3024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6232  -16.7165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6246  -15.4678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3400  -15.0569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9110  -15.0538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1928  -12.5796    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  6
 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:

   

   ALA4649652

   ---

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