[4-fluoro-5-(5-fluoro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-hydroxytetrahydrofuran-2-yl]methyl dihydrogen phosphate (FFara-UMP)

ID: ALA253954

Cas Number: 85894-46-8

PubChem CID: 174519

Max Phase: Preclinical

Molecular Formula: C9H11F2N2O8P

Molecular Weight: 344.16

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1[nH]c(=O)n([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@@H]2F)cc1F

Standard InChI:  InChI=1S/C9H11F2N2O8P/c10-3-1-13(9(16)12-7(3)15)8-5(11)6(14)4(21-8)2-20-22(17,18)19/h1,4-6,8,14H,2H2,(H,12,15,16)(H2,17,18,19)/t4-,5+,6-,8-/m1/s1

Standard InChI Key:  FEEBOLVDMGNROC-BYPJNBLXSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  1  0  0  0  0  0999 V2000
   11.0776  -14.2768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9026  -14.2768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1576  -13.4922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4901  -13.0072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8227  -13.4922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9423  -13.2363    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6707  -13.6334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3698  -13.2022    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3482  -12.3772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6212  -11.9852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9159  -12.4181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6928  -14.4580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0509  -11.9452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0381  -13.2372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4251  -13.7893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6405  -13.5344    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    7.8419  -13.3188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8755  -12.7435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4076  -14.3258    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5926  -14.9441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5981  -11.1605    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.3875  -14.9442    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0
 10 11  2  0
  1  2  1  0
  7 12  2  0
  3  6  1  1
  9 13  2  0
  6  7  1  0
  5 14  1  1
 14 15  1  0
  2  3  1  0
 15 16  1  0
  3  4  1  0
 16 17  1  0
  4  5  1  0
 16 18  2  0
  5  1  1  0
 16 19  1  0
  6 11  1  0
  1 20  1  6
  7  8  1  0
 10 21  1  0
  8  9  1  0
  2 22  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA253954

   2',5-Difluoro-1-arabinosyluridine monophosphate

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: 344.16

Molecular Weight (Monoisotopic): 344.0221

AlogP: -1.62

#Rotatable Bonds: 4

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: 1.22

CX Basic pKa: ┄

CX LogP: -1.45

CX LogD: -5.05

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.48

Np Likeness Score: 0.68

References

1. Coderre JA, Santi DV, Matsuda A, Watanabe KA, Fox JJ..  (1983)  Mechanism of action of 2',5-difluoro-1-arabinosyluracil.,  26  (8): [PMID:6876083] [10.1021/jm00362a012]

2. Jarmuła A, Dowierciał A, Rode W..  (2008)  A molecular modeling study of the interaction of 2'-fluoro-substituted analogues of dUMP/FdUMP with thymidylate synthase.,  18  (8): [PMID:18362071] [10.1016/j.bmcl.2008.03.016]

Source

Source(1):

• Scientific Literature