Pentyl (((((S)-1-((4-amino-5-fluoropyrimidin-2-yl)oxy)propan-2-yl)oxy)methyl)(phenoxy)phosphoryl)-L-valinate

ID: ALA4635303

PubChem CID: 156014477

Max Phase: Preclinical

Molecular Formula: C24H36FN4O6P

Molecular Weight: 526.55

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCCCOC(=O)[C@@H](NP(=O)(CO[C@@H](C)COc1ncc(F)c(N)n1)Oc1ccccc1)C(C)C

Standard InChI:  InChI=1S/C24H36FN4O6P/c1-5-6-10-13-32-23(30)21(17(2)3)29-36(31,35-19-11-8-7-9-12-19)16-34-18(4)15-33-24-27-14-20(25)22(26)28-24/h7-9,11-12,14,17-18,21H,5-6,10,13,15-16H2,1-4H3,(H,29,31)(H2,26,27,28)/t18-,21-,36?/m0/s1

Standard InChI Key:  PJIZTVUNWQKFLB-RCFCJROFSA-N

Molfile:  

 
     RDKit          2D

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   17.9870   -4.9735    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   22.2777   -5.7921    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
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   16.5588   -3.3209    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
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 18 32  1  1
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  1 35  1  0
 31 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4635303

   ---

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: 526.55

Molecular Weight (Monoisotopic): 526.2356

AlogP: 4.56

#Rotatable Bonds: 16

Polar Surface Area: 134.89

Molecular Species: NEUTRAL

HBA: 9

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.34

CX Basic pKa: 3.27

CX LogP: 4.40

CX LogD: 4.40

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.18

Np Likeness Score: -0.43

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