4-[1-(4-Hydroxy-5-phosphonooxymethyl-tetrahydro-furan-2-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-benzoic acid methyl ester

ID: ALA3144197

PubChem CID: 90663798

Max Phase: Preclinical

Molecular Formula: C17H19N2O10P

Molecular Weight: 442.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)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/C17H19N2O10P/c1-27-16(22)10-4-2-9(3-5-10)11-7-19(17(23)18-15(11)21)14-6-12(20)13(29-14)8-28-30(24,25)26/h2-5,7,12-14,20H,6,8H2,1H3,(H,18,21,23)(H2,24,25,26)/t12-,13+,14+/m0/s1

Standard InChI Key:  XGPHCIFEWUNDER-BFHYXJOUSA-N

Molfile:  

     RDKit          2D

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    4.7286   -9.7912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2135  -10.4586    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3695   -9.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5792   -8.3700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0340  -10.3724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8846   -8.9513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4522   -5.0380    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.8342   -7.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7542   -8.3700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1667   -7.1005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4993   -7.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1900   -9.5325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6515   -9.2737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1667   -6.2755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9081   -9.8774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4522   -5.8630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4522   -4.2130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2772   -5.0380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9870   -8.5201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6749  -10.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5256   -8.7788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3461   -8.6925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4954  -10.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1364   -9.9412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7147   -7.3305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9569   -9.8549    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
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  8 17  1  0
  9  5  1  0
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 14 21  1  0
 11 15  1  1
 16  2  2  0
 17 15  1  0
 18  8  1  0
 19  8  1  0
 20  6  2  0
 21 26  1  0
 22  8  2  0
 23 14  2  0
 24 13  2  0
 25 13  1  0
 26 25  2  0
 27 24  1  0
 28 14  1  0
 12 29  1  6
 30 28  1  0
  6  3  1  0
 12 11  1  0
 21 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3144197

   4-[1-(4-Hydroxy-5-phosphonooxymethyl-tetrahydro-furan-2-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-benzoic acid methyl ester

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: 442.32

Molecular Weight (Monoisotopic): 442.0777

AlogP: -0.25

#Rotatable Bonds: 6

Polar Surface Area: 177.38

Molecular Species: ACID

HBA: 9

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 12

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 1.23

CX Basic pKa: ┄

CX LogP: 0.03

CX LogD: -3.49

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.34

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