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

ID: ALA4639887

PubChem CID: 156014826

Max Phase: Preclinical

Molecular Formula: C18H31N4O6P

Molecular Weight: 430.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCCCOC(=O)[C@@H](NP1(=O)CO[C@H](COc2nccc(N)n2)CO1)C(C)C

Standard InChI:  InChI=1S/C18H31N4O6P/c1-4-5-6-9-25-17(23)16(13(2)3)22-29(24)12-27-14(11-28-29)10-26-18-20-8-7-15(19)21-18/h7-8,13-14,16H,4-6,9-12H2,1-3H3,(H,22,24)(H2,19,20,21)/t14-,16+,29?/m1/s1

Standard InChI Key:  ANBLXARAOKNPIH-ILUNRSFJSA-N

Molfile:  

 
     RDKit          2D

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    4.5121  -13.2189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5093  -12.3883    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7914  -11.1542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    6.6534  -14.4479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    9.5090  -16.9320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9399  -16.1101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6553  -15.6992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3688  -16.1133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0842  -15.7024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7978  -16.1165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.5145  -14.4570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0856  -14.4538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 27 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4639887

   ---

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: 430.44

Molecular Weight (Monoisotopic): 430.1981

AlogP: 2.35

#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: 13.51

CX Basic pKa: 5.84

CX LogP: 2.08

CX LogD: 2.07

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.31

Np Likeness Score: -0.12

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