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

ID: ALA3144193

PubChem CID: 90663794

Max Phase: Preclinical

Molecular Formula: C16H16N3O8P

Molecular Weight: 409.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1ccc(-c2cn([C@H]3C[C@H](O)[C@@H](COP(=O)(O)O)O3)c(=O)[nH]c2=O)cc1

Standard InChI:  InChI=1S/C16H16N3O8P/c17-6-9-1-3-10(4-2-9)11-7-19(16(22)18-15(11)21)14-5-12(20)13(27-14)8-26-28(23,24)25/h1-4,7,12-14,20H,5,8H2,(H,18,21,22)(H2,23,24,25)/t12-,13+,14+/m0/s1

Standard InChI Key:  HDOUTIGHYBDMMB-BFHYXJOUSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    4.8616   -8.8515    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5260   -9.6052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0109  -10.2726    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1670   -9.4327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3766   -8.1841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8314  -10.1864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6820   -8.7653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6786   -4.8520    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.6316   -7.3995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5516   -8.1841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9641   -6.9145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2967   -7.3995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2694   -9.0015    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9874   -9.3465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9641   -6.0895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4489   -9.0878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7055   -9.6914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6786   -5.6770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6786   -4.0270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5036   -4.8520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3163  -10.8538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8536   -4.8520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4724  -10.0139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3230   -8.5928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6284   -9.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5121   -7.1445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2928   -9.9277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1435   -8.5066    0.0000 C   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 18  1  0
  9  5  1  0
 10  5  1  0
 11  9  1  0
 12 10  1  0
 13 16  3  0
 14  4  1  0
 11 15  1  1
 16 25  1  0
 17  2  2  0
 18 15  1  0
 19  8  1  0
 20  8  1  0
 21  6  2  0
 22  8  2  0
 23 14  2  0
 24 14  1  0
 25 28  1  0
 12 26  1  6
 27 23  1  0
 28 24  2  0
  6  3  1  0
 11 12  1  0
 27 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3144193

   [(2R,3S,5R)-5-[5-(4-cyanophenyl)-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: 409.29

Molecular Weight (Monoisotopic): 409.0675

AlogP: -0.17

#Rotatable Bonds: 5

Polar Surface Area: 174.87

Molecular Species: ACID

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 1.23

CX Basic pKa: ┄

CX LogP: -0.11

CX LogD: -3.64

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.49

Np Likeness Score: 0.35

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