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

ID: ALA3144192

PubChem CID: 90663793

Max Phase: Preclinical

Molecular Formula: C17H22N3O8P

Molecular Weight: 427.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)c1ccc(-c2cn([C@H]3C[C@H](O)[C@@H](COP(=O)(O)O)O3)c(=O)[nH]c2=O)cc1

Standard InChI:  InChI=1S/C17H22N3O8P/c1-19(2)11-5-3-10(4-6-11)12-8-20(17(23)18-16(12)22)15-7-13(21)14(28-15)9-27-29(24,25)26/h3-6,8,13-15,21H,7,9H2,1-2H3,(H,18,22,23)(H2,24,25,26)/t13-,14+,15+/m0/s1

Standard InChI Key:  ZWVQFRZANSMQRB-RRFJBIMHSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
    2.8539   -1.7346    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5183   -2.4883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0033   -3.1558    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1593   -2.3158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3690   -1.0672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8237   -3.0695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6744   -1.6484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2420    2.2648    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.6239   -0.2826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5440   -1.0672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9565    0.2023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2890   -0.2826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9798   -2.2296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9565    1.0273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6979   -2.5745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2420    1.4398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2420    3.0898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4170    2.2648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3087   -3.7370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0670    2.2648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6207   -2.0571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4412   -1.9709    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4647   -2.8970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3153   -1.4759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1358   -1.3897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2852   -2.8108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5044   -0.0276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7768   -1.2172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9261   -2.6383    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 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 25  1  0
 22 21  1  0
 23 13  2  0
 24 13  1  0
 25 24  2  0
 26 23  1  0
 12 27  1  6
 28 22  1  0
 29 22  1  0
  6  3  1  0
 11 12  1  0
 26 21  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3144192

   [(2R,3S,5R)-5-[5-[4-(dimethylamino)phenyl]-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: 427.35

Molecular Weight (Monoisotopic): 427.1145

AlogP: 0.03

#Rotatable Bonds: 6

Polar Surface Area: 154.32

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: 4.02

CX LogP: -0.94

CX LogD: -3.38

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.47

Np Likeness Score: 0.42

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