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

ID: ALA3142384

PubChem CID: 14804296

Max Phase: Preclinical

Molecular Formula: C19H27BrN3O7PS2

Molecular Weight: 584.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1CC(CC2SCCCS2)OP1(=O)OC[C@H]1O[C@@H](n2cc(/C=C/Br)c(=O)[nH]c2=O)C[C@@H]1O

Standard InChI:  InChI=1S/C19H27BrN3O7PS2/c1-22-10-13(7-17-32-5-2-6-33-17)30-31(22,27)28-11-15-14(24)8-16(29-15)23-9-12(3-4-20)18(25)21-19(23)26/h3-4,9,13-17,24H,2,5-8,10-11H2,1H3,(H,21,25,26)/b4-3+/t13?,14-,15+,16+,31?/m0/s1

Standard InChI Key:  RYYURYAVRLGORX-IQSQABHESA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
    2.2829   -1.0341    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2573   -4.1287    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    3.0366   -0.6985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1228    0.1220    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1967   -1.8545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7017    0.2713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6155   -0.5491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4554    0.6069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9247   -4.6136    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4101   -4.6136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4822   -2.2670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8098   -2.4066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1552   -5.3982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6537   -3.0740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2947   -3.5156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4742   -3.1603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6401   -6.0657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8093   -3.5156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1017   -3.6871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3046   -6.8193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0343    0.7563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7040   -1.1834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5159   -6.9056    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7895   -7.4868    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.5416    1.4274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1205    1.5767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4531    2.0617    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.8867   -3.8747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7094   -4.3587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3665   -8.3267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4539   -8.2405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8515   -7.6592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2 15  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  2  1  0
 10  2  1  0
 11  5  1  0
 12  5  1  0
 13 10  1  0
 14 11  1  0
 15 20  1  0
 16  9  1  0
 17 12  1  0
 18 13  1  0
 19  2  2  0
 14 20  1  1
 21 18  1  0
 22  6  1  0
 23  3  2  0
 24 21  1  0
 25 21  1  0
 26  8  2  0
 27 22  2  0
 28 27  1  0
 17 29  1  6
 30  9  1  0
 31 32  1  0
 32 25  1  0
 33 24  1  0
  4  8  1  0
 17 14  1  0
 13 16  1  0
 31 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3142384

   5-[(E)-2-bromoethenyl]-1-[(2R,4S,5R)-5-[[5-(1,3-dithian-2-ylmethyl)-3-methyl-2-oxo-1,3,2lambda5-oxazaphospholidin-2-yl]oxymethyl]-4-hydroxyoxolan-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: 584.45

Molecular Weight (Monoisotopic): 583.0211

AlogP: 2.59

#Rotatable Bonds: 7

Polar Surface Area: 123.09

Molecular Species: NEUTRAL

HBA: 10

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.74

CX Basic pKa: ┄

CX LogP: 1.30

CX LogD: 1.30

Aromatic Rings: 1

Heavy Atoms: 33

QED Weighted: 0.46

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