5-((E)-2-Bromo-vinyl)-1-[4-hydroxy-5-(3-methyl-2-oxo-2lambda*5*-[1,3,2]oxazaphospholidin-2-yloxymethyl)-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

ID: ALA3142383

PubChem CID: 14804289

Max Phase: Preclinical

Molecular Formula: C14H19BrN3O7P

Molecular Weight: 452.20

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1CCOP1(=O)OC[C@H]1O[C@@H](n2cc(/C=C/Br)c(=O)[nH]c2=O)C[C@@H]1O

Standard InChI:  InChI=1S/C14H19BrN3O7P/c1-17-4-5-23-26(17,22)24-8-11-10(19)6-12(25-11)18-7-9(2-3-15)13(20)16-14(18)21/h2-3,7,10-12,19H,4-6,8H2,1H3,(H,16,20,21)/b3-2+/t10-,11+,12+,26?/m0/s1

Standard InChI Key:  AFWGRKKHYTUCCB-COTXRJKUSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   -0.6239    1.2563    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1023   -2.7945    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.1297    1.5919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2160    2.4123    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7102    0.4358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2052    2.5617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2914    1.7412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4515    2.8973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4247    0.0233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7697   -3.2794    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0971   -0.1162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2531   -0.7836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5502   -2.1814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4348   -3.2794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4326   -0.8699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6543   -2.1814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8052   -1.3967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8726    3.0466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7972    1.1069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3652    3.7177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6898   -4.0640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5148   -4.0640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7864    3.8671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4538    4.3520    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.0201   -1.5844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5543   -3.0244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2 13  1  0
  3  1  1  0
  4  3  1  0
  5  1  1  1
  6  7  2  0
  7  1  1  0
  8  6  1  0
  9  5  1  0
 10  2  1  0
 11  5  1  0
 12  9  1  0
 13 17  1  0
 14  2  1  0
 15 11  1  0
 16  2  2  0
 12 17  1  1
 18  6  1  0
 19  3  2  0
 20  8  2  0
 21 14  1  0
 22 10  1  0
 23 18  2  0
 24 23  1  0
 15 25  1  6
 26 10  1  0
  4  8  1  0
 15 12  1  0
 21 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3142383

   5-[(E)-2-bromoethenyl]-1-[(2R,4S,5R)-4-hydroxy-5-[(3-methyl-2-oxo-1,3,2lambda5-oxazaphospholidin-2-yl)oxymethyl]oxolan-2-yl]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: 452.20

Molecular Weight (Monoisotopic): 451.0144

AlogP: 0.64

#Rotatable Bonds: 5

Polar Surface Area: 123.09

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.74

CX Basic pKa: ┄

CX LogP: -0.54

CX LogD: -0.54

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.62

Np Likeness Score: 0.66

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