2-(5-[1,3]Dithian-2-ylmethyl-3-methyl-2-oxo-2lambda*5*-[1,3,2]oxazaphospholidin-2-yloxyamino)-9-(2-hydroxy-ethoxymethyl)-1,2,3,9-tetrahydro-purin-6-one

ID: ALA80550

PubChem CID: 44316309

Max Phase: Preclinical

Molecular Formula: C16H27N6O6PS2

Molecular Weight: 494.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1CC(CC2SCCCS2)OP1(=O)ONC1NC(=O)c2ncn(COCCO)c2N1

Standard InChI:  InChI=1S/C16H27N6O6PS2/c1-21-8-11(7-12-30-5-2-6-31-12)27-29(21,25)28-20-16-18-14-13(15(24)19-16)17-9-22(14)10-26-4-3-23/h9,11-12,16,18,20,23H,2-8,10H2,1H3,(H,19,24)

Standard InChI Key:  WUAZDAHYLNZCPU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -1.3708    1.2083    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.8917   -1.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2750   -2.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7292   -0.7667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6042   -2.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6042   -2.8917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5083   -1.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6750   -1.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7458    1.8583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0583   -0.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7458    0.5583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4958    0.5583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4958    1.8583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2208   -1.5000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9333   -0.2542    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1250   -2.4167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3625   -1.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7458    2.6083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0292   -2.1542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6583   -1.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9375   -1.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6458   -0.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2042   -1.9792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4500   -2.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7792   -1.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0
  3  7  1  0
  4 10  1  0
  5  2  1  0
  6  3  1  0
  7  8  1  0
  8 10  1  0
  9  1  1  0
 10 14  1  0
 11  1  1  0
 12  5  1  0
 13  1  1  0
 14 13  1  0
 15 11  1  0
 16  9  1  0
 17 15  1  0
 18  1  2  0
 19 17  1  0
 20 19  1  0
 21 19  1  0
 22  7  2  0
 23  5  1  0
 24  9  1  0
 25 23  1  0
 26 28  1  0
 27 20  1  0
 28 21  1  0
 29 30  1  0
 30 31  1  0
 31 25  1  0
 16 15  1  0
  3  2  2  0
 26 27  1  0
 12  6  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA80550

   2-[[5-(1,3-dithian-2-ylmethyl)-3-methyl-2-oxo-1,3,2lambda5-oxazaphospholidin-2-yl]oxyamino]-9-(2-hydroxyethoxymethyl)-2,3-dihydro-1H-purin-6-one

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: 494.54

Molecular Weight (Monoisotopic): 494.1171

AlogP: 0.83

#Rotatable Bonds: 9

Polar Surface Area: 139.21

Molecular Species: NEUTRAL

HBA: 12

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 4.55

CX LogP: 0.48

CX LogD: 0.48

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.22

Np Likeness Score: -0.14

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