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

ID: ALA1258777

PubChem CID: 49782092

Max Phase: Preclinical

Molecular Formula: C29H53N6O5P

Molecular Weight: 596.75

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCCCCCCCCOCCO[P@@]1(=O)CO[C@@H](Cn2cnc3c(N)nc(N)nc32)CO1

Standard InChI:  InChI=1S/C29H53N6O5P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-37-19-20-39-41(36)24-38-25(22-40-41)21-35-23-32-26-27(30)33-29(31)34-28(26)35/h23,25H,2-22,24H2,1H3,(H4,30,31,33,34)/t25-,41-/m0/s1

Standard InChI Key:  RUOVJFVKCPQOBR-DECSIMMDSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA1258777

   9-[[(2S,5S)-2-(2-octadecoxyethoxy)-2-oxo-1,4,2lambda5-dioxaphosphinan-5-yl]methyl]purine-2,6-diamine

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: 596.75

Molecular Weight (Monoisotopic): 596.3815

AlogP: 6.85

#Rotatable Bonds: 23

Polar Surface Area: 149.63

Molecular Species: NEUTRAL

HBA: 11

HBD: 2

#RO5 Violations: 3

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 3

CX Acidic pKa: ┄

CX Basic pKa: 6.04

CX LogP: 6.36

CX LogD: 6.34

Aromatic Rings: 2

Heavy Atoms: 41

QED Weighted: 0.10

Np Likeness Score: -0.22

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