2-Amino-9-[2-(3-methyl-2-oxo-2lambda*5*-[1,3,2]oxazaphospholidin-2-yloxy)-ethoxymethyl]-5,9-dihydro-purin-6-one

ID: ALA421327

PubChem CID: 136171380

Max Phase: Preclinical

Molecular Formula: C11H17N6O5P

Molecular Weight: 344.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1CCOP1(=O)OCCOCn1cnc2c(O)nc(N)nc21

Standard InChI:  InChI=1S/C11H17N6O5P/c1-16-2-3-21-23(16,19)22-5-4-20-7-17-6-13-8-9(17)14-11(12)15-10(8)18/h6H,2-5,7H2,1H3,(H3,12,14,15,18)

Standard InChI Key:  WFZPCAZAPRMLKU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    6.3208   -1.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5417   -2.1875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3042   -3.3375    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    5.0958   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4958   -1.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0458   -2.3500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8833   -0.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9292   -1.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3208   -1.0375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6583   -1.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6958   -2.7875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9583   -4.0875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5833   -2.5625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0542    0.2292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8208   -3.9708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0208   -4.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1417   -4.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1458   -1.8958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9792   -3.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6333   -3.8333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5458   -1.9708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8333   -3.9208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0542   -4.7333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3 15  1  0
  4  7  1  0
  5  1  1  0
  6  1  1  0
  7  5  2  0
  8  2  1  0
  9  5  1  0
 10  6  1  0
 11  3  1  0
 12  3  1  0
 13  3  2  0
 14  7  1  0
 15 20  1  0
 16  6  1  0
 17 12  1  0
 18  8  1  0
 19 11  1  0
 20 23  1  0
 21 11  1  0
 22 16  1  0
 23 22  1  0
 10  9  2  0
  4  8  2  0
 19 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA421327

   ---

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: 344.27

Molecular Weight (Monoisotopic): 344.0998

AlogP: 0.17

#Rotatable Bonds: 6

Polar Surface Area: 137.85

Molecular Species: NEUTRAL

HBA: 10

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.58

CX Basic pKa: 1.01

CX LogP: -0.60

CX LogD: -0.60

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.55

Np Likeness Score: -0.51

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