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

ID: ALA3144195

PubChem CID: 90663796

Max Phase: Preclinical

Molecular Formula: C16H18N3O9P

Molecular Weight: 427.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(=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/C16H18N3O9P/c17-14(21)9-3-1-8(2-4-9)10-6-19(16(23)18-15(10)22)13-5-11(20)12(28-13)7-27-29(24,25)26/h1-4,6,11-13,20H,5,7H2,(H2,17,21)(H,18,22,23)(H2,24,25,26)/t11-,12+,13+/m0/s1

Standard InChI Key:  IRZJBSZMYWHGTO-YNEHKIRRSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
    4.7428   -9.1367    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4073   -9.8903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8922  -10.5578    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0482   -9.7179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2579   -8.4692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7127  -10.4715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5633   -9.0504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1309   -5.1372    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.5128   -7.6846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4329   -8.4692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8454   -7.1997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1780   -7.6846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3301   -9.3729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8687   -9.6316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8454   -6.3747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5868   -9.9766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1309   -5.9622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1309   -4.3122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3059   -5.1372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1976  -11.1390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5097   -9.4591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9559   -5.1372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6657   -8.6192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3536  -10.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2043   -8.8779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0247   -8.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1741  -10.2128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8151  -10.0403    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3933   -7.4297    0.0000 O   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 17  1  0
  9  5  1  0
 10  5  1  0
 11  9  1  0
 12 10  1  0
 13 21  1  0
 14  4  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 13  2  0
 24 14  2  0
 25 14  1  0
 26 25  2  0
 27 24  1  0
 28 13  1  0
 12 29  1  6
  6  3  1  0
 12 11  1  0
 21 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3144195

   [(2R,3S,5R)-5-[5-(4-carbamoylphenyl)-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: 427.31

Molecular Weight (Monoisotopic): 427.0781

AlogP: -0.94

#Rotatable Bonds: 6

Polar Surface Area: 194.17

Molecular Species: ACID

HBA: 8

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 12

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.24

CX Basic pKa: ┄

CX LogP: -1.28

CX LogD: -4.65

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.36

Np Likeness Score: 0.48

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