5-(5-[1,3]Dithian-2-ylmethyl-3-methyl-2-oxo-2lambda*5*-[1,3,2]oxazaphospholidin-2-yloxy)-1H-pyrimidine-2,4-dione

ID: ALA80477

PubChem CID: 44316068

Max Phase: Preclinical

Molecular Formula: C12H18N3O5PS2

Molecular Weight: 379.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1CC(CC2SCCCS2)OP1(=O)Oc1cnc(O)nc1O

Standard InChI:  InChI=1S/C12H18N3O5PS2/c1-15-7-8(5-10-22-3-2-4-23-10)19-21(15,18)20-9-6-13-12(17)14-11(9)16/h6,8,10H,2-5,7H2,1H3,(H2,13,14,16,17)

Standard InChI Key:  HKSOOROQSDOSGM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   -1.5250    0.3750    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.4625   -0.3250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0292   -0.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1000    0.9708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7417    0.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9083   -0.3542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6833    0.0833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4625   -1.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7208   -0.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0292   -1.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500   -1.5667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8375    0.6083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1208    1.0958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7333   -1.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4458   -1.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1583   -1.0250    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4500   -2.2667    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7417    0.9083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1750   -1.5667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9583    1.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8833   -2.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1625   -2.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8708   -1.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  5  2  0
  3  7  1  0
  4  1  1  0
  5  3  1  0
  6  1  1  0
  7  1  1  0
  8 11  2  0
  9  6  1  0
 10  3  2  0
 11 10  1  0
 12  4  1  0
 13  1  2  0
 14  9  1  0
 15 14  1  0
 16 15  1  0
 17 15  1  0
 18  5  1  0
 19  8  1  0
 20  4  1  0
 21 22  1  0
 22 17  1  0
 23 16  1  0
  9 12  1  0
  8  2  1  0
 21 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA80477

   5-[[5-(1,3-dithian-2-ylmethyl)-3-methyl-2-oxo-1,3,2lambda5-oxazaphospholidin-2-yl]oxy]-1H-pyrimidine-2,4-dione

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: 379.40

Molecular Weight (Monoisotopic): 379.0425

AlogP: 2.29

#Rotatable Bonds: 4

Polar Surface Area: 105.01

Molecular Species: NEUTRAL

HBA: 9

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.60

CX Basic pKa: ┄

CX LogP: 2.33

CX LogD: 2.33

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.76

Np Likeness Score: -0.06

References

1. Kumar A, Coe PL, Jones AS, Walker RT, Balzarini J, De Clercq E..  (1990)  Synthesis and biological evaluation of some cyclic phosphoramidate nucleoside derivatives.,  33  (9): [PMID:2391680] [10.1021/jm00171a009]

Source

Source(1):

• Scientific Literature