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

ID: ALA3144189

PubChem CID: 90663790

Max Phase: Preclinical

Molecular Formula: C15H18N3O8P

Molecular Weight: 399.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ccc(-c2cn([C@H]3C[C@H](O)[C@@H](COP(=O)(O)O)O3)c(=O)[nH]c2=O)cc1

Standard InChI:  InChI=1S/C15H18N3O8P/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,5,7,16H2,(H,17,20,21)(H2,22,23,24)/t11-,12+,13+/m0/s1

Standard InChI Key:  VOVNIQUVTRDMGX-YNEHKIRRSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    5.1224   -9.4177    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7868  -10.1714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2717  -10.8388    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4278   -9.9989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6374   -8.7503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0922  -10.7526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9428   -9.3315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5105   -5.4182    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.8924   -7.9657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8124   -8.7503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2249   -7.4807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5575   -7.9657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2482   -9.9127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2249   -6.6557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9663  -10.2576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5105   -6.2432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5105   -4.5932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6855   -5.4182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5771  -11.4200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3355   -5.4182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7332  -10.5801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5838   -9.1590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8892   -9.7402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7729   -7.7107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7097   -9.6540    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5536  -10.4939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4043   -9.0728    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 13  2  0
 22 13  1  0
 23 27  1  0
 12 24  1  6
 25 23  1  0
 26 21  1  0
 27 22  2  0
  3  6  1  0
 12 11  1  0
 23 26  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3144189

   [(2R,3S,5R)-5-[5-(4-aminophenyl)-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: 399.30

Molecular Weight (Monoisotopic): 399.0832

AlogP: -0.46

#Rotatable Bonds: 5

Polar Surface Area: 177.10

Molecular Species: ACID

HBA: 8

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.23

CX Basic pKa: 3.31

CX LogP: -1.10

CX LogD: -4.32

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.33

Np Likeness Score: 0.75

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