Phosphoric acid mono-{5-[5-(4-bromo-phenyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-3-hydroxy-tetrahydro-furan-2-ylmethyl} ester

ID: ALA3144196

PubChem CID: 90663797

Max Phase: Preclinical

Molecular Formula: C15H16BrN2O8P

Molecular Weight: 463.18

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1[nH]c(=O)n([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)cc1-c1ccc(Br)cc1

Standard InChI:  InChI=1S/C15H16BrN2O8P/c16-9-3-1-8(2-4-9)10-6-18(15(21)17-14(10)20)13-5-11(19)12(26-13)7-25-27(22,23)24/h1-4,6,11-13,19H,5,7H2,(H,17,20,21)(H2,22,23,24)/t11-,12+,13+/m0/s1

Standard InChI Key:  BPABLZCEPTUPRF-YNEHKIRRSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    5.4003   -9.0052    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0647   -9.7589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5497  -10.4263    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7057   -9.5864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9154   -8.3378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3701  -10.3401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2208   -8.9190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7884   -5.0057    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    5.1703   -7.5532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0904   -8.3378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5029   -7.0682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8354   -7.5532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5262   -9.5002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5029   -6.2432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2443   -9.8451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7884   -5.8307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7884   -4.1807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9634   -5.0057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8551  -11.0075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6134   -5.0057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0111  -10.1676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8617   -8.7465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1671   -9.3277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0508   -7.2982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8316  -10.0814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6822   -8.6603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9876   -9.2415    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  7  2  0
  5  1  1  1
  6  4  1  0
  7  1  1  0
  8 16  1  0
  9  5  1  0
 10  5  1  0
 11  9  1  0
 12 10  1  0
 13  4  1  0
 11 14  1  1
 15  2  2  0
 16 14  1  0
 17  8  1  0
 18  8  1  0
 19  6  2  0
 20  8  2  0
 21 13  2  0
 22 13  1  0
 23 26  1  0
 12 24  1  6
 25 21  1  0
 26 22  2  0
 27 23  1  0
  3  6  1  0
 12 11  1  0
 23 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3144196

   [(2R,3S,5R)-5-[5-(4-bromophenyl)-2,4-dioxopyrimidin-1-yl]-3-hydroxyoxolan-2-yl]methyl dihydrogen phosphate

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: 463.18

Molecular Weight (Monoisotopic): 461.9828

AlogP: 0.72

#Rotatable Bonds: 5

Polar Surface Area: 151.08

Molecular Species: ACID

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.23

CX Basic pKa: ┄

CX LogP: 0.80

CX LogD: -2.73

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.47

Np Likeness Score: 0.61

References

1. Chang G, Schwepler D, Decedue CJ, Balzarini J, De Clercq E, Mertes MP..  (1988)  Linear free energy relationship studies of enzyme active site binding: thymidylate synthase.,  31  (6): [PMID:3373483] [10.1021/jm00401a013]

Source

Source(1):

• Scientific Literature