((2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl (2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl hydrogen phosphate

ID: ALA3608398

Cas Number: 1969-54-6

PubChem CID: 449179

Max Phase: Preclinical

Molecular Formula: C20H27N4O12P

Molecular Weight: 546.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cn([C@H]2C[C@H](OP(=O)(O)OC[C@H]3O[C@@H](n4cc(C)c(=O)[nH]c4=O)C[C@@H]3O)[C@@H](CO)O2)c(=O)[nH]c1=O

Standard InChI:  InChI=1S/C20H27N4O12P/c1-9-5-23(19(29)21-17(9)27)15-3-11(26)14(35-15)8-33-37(31,32)36-12-4-16(34-13(12)7-25)24-6-10(2)18(28)22-20(24)30/h5-6,11-16,25-26H,3-4,7-8H2,1-2H3,(H,31,32)(H,21,27,29)(H,22,28,30)/t11-,12-,13+,14+,15+,16+/m0/s1

Standard InChI Key:  FCXGCSBZKOHCLB-KPRKPIBOSA-N

Molfile:  

     RDKit          2D

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    2.5987   -1.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7343   -2.9815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 24 37  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA3608398

   Dithymidine phosphate

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: 546.43

Molecular Weight (Monoisotopic): 546.1363

AlogP: -1.87

#Rotatable Bonds: 8

Polar Surface Area: 224.40

Molecular Species: ACID

HBA: 13

HBD: 5

#RO5 Violations: 2

HBA (Lipinski): 16

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.86

CX Basic pKa: ┄

CX LogP: -1.47

CX LogD: -3.84

Aromatic Rings: 2

Heavy Atoms: 37

QED Weighted: 0.23

Np Likeness Score: 0.82

References

1. Hayashi J, Hamada T, Sasaki I, Nakagawa O, Wada S, Urata H..  (2015)  Synthesis of novel cationic spermine-conjugated phosphotriester oligonucleotide for improvement of cell membrane permeability.,  25  (17): [PMID:26149182] [10.1016/j.bmcl.2015.06.071]

Source

Source(1):

• Scientific Literature