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

ID: ALA3144194

PubChem CID: 90663795

Max Phase: Preclinical

Molecular Formula: C16H16F3N2O8P

Molecular Weight: 452.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1[nH]c(=O)n([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)cc1-c1ccc(C(F)(F)F)cc1

Standard InChI:  InChI=1S/C16H16F3N2O8P/c17-16(18,19)9-3-1-8(2-4-9)10-6-21(15(24)20-14(10)23)13-5-11(22)12(29-13)7-28-30(25,26)27/h1-4,6,11-13,22H,5,7H2,(H,20,23,24)(H2,25,26,27)/t11-,12+,13+/m0/s1

Standard InChI Key:  KCWQZALHXQHMOQ-YNEHKIRRSA-N

Molfile:  

     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
    5.1035   -9.0421    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7679   -9.7958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2528  -10.4633    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4089   -9.6233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6186   -8.3747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0733  -10.3770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9240   -8.9559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4916   -5.0427    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.8735   -7.5901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7936   -8.3747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6908   -9.2784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2061   -7.1052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5386   -7.5901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2294   -9.5371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2061   -6.2802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8703   -9.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9474   -9.8820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4916   -5.8677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4916   -4.2177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6666   -5.0427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5583  -11.0445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3166   -5.0427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7143  -10.2045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5649   -8.7834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3854   -8.6972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5348  -10.1183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5113   -9.1922    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.7770  -10.0989    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.6046   -8.4579    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.7540   -7.3351    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 18  1  0
  9  5  1  0
 10  5  1  0
 11 16  1  0
 12  9  1  0
 13 10  1  0
 14  4  1  0
 12 15  1  1
 16 25  2  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  1  0
 24 14  2  0
 25 24  1  0
 26 23  2  0
 27 11  1  0
 28 11  1  0
 29 11  1  0
 13 30  1  6
  3  6  1  0
 12 13  1  0
 16 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3144194

   [(2R,3S,5R)-5-[2,4-dioxo-5-[4-(trifluoromethyl)phenyl]pyrimidin-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: 452.28

Molecular Weight (Monoisotopic): 452.0596

AlogP: 0.98

#Rotatable Bonds: 5

Polar Surface Area: 151.08

Molecular Species: ACID

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.23

CX Basic pKa: ┄

CX LogP: 0.91

CX LogD: -2.62

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.49

Np Likeness Score: 0.34

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