Butylsalicyl Ester 9-{[(5S)-2-Hydroxy-2-oxido-1,4,2-dioxaphosphinan-5-yl]methyl}-2,6-diaminopurine

ID: ALA1257279

PubChem CID: 52944919

Max Phase: Preclinical

Molecular Formula: C20H25N6O6P

Molecular Weight: 476.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCOC(=O)c1ccccc1OP1(=O)CO[C@@H](Cn2cnc3c(N)nc(N)nc32)CO1

Standard InChI:  InChI=1S/C20H25N6O6P/c1-2-3-8-29-19(27)14-6-4-5-7-15(14)32-33(28)12-30-13(10-31-33)9-26-11-23-16-17(21)24-20(22)25-18(16)26/h4-7,11,13H,2-3,8-10,12H2,1H3,(H4,21,22,24,25)/t13-,33?/m0/s1

Standard InChI Key:  NWLSPSCDCQLNIZ-OHFQDIGNSA-N

Molfile:  

     RDKit          2D

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    1.2982   -1.5145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0501   -0.8215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7222   -2.2213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5463   -2.2075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9703   -2.9143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3596    1.2024    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  6  2  1  0
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  1 19  1  0
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 24 25  1  0
 25 26  1  0
 25 27  2  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
  5 32  1  0
  3 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1257279

   butyl 2-[[(5S)-5-[(2,6-diaminopurin-9-yl)methyl]-2-oxo-1,4,2$l^{5}-dioxaphosphinan-2-yl]oxy]benzoate

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 476.43

Molecular Weight (Monoisotopic): 476.1573

AlogP: 2.59

#Rotatable Bonds: 8

Polar Surface Area: 166.70

Molecular Species: NEUTRAL

HBA: 12

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 6.04

CX LogP: 2.30

CX LogD: 2.29

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.28

Np Likeness Score: -0.42

References

1. Krecmerová M, Holý A, Andrei G, Pomeisl K, Tichý T, Brehová P, Masojídková M, Dracínský M, Pohl R, Laflamme G, Naesens L, Hui H, Cihlar T, Neyts J, De Clercq E, Balzarini J, Snoeck R..  (2010)  Synthesis of ester prodrugs of 9-(S)-[3-hydroxy-2-(phosphonomethoxy)propyl]-2,6-diaminopurine (HPMPDAP) as anti-poxvirus agents.,  53  (19): [PMID:20809641] [10.1021/jm901828c]

Source

Source(1):

• Scientific Literature