5-Difluoromethyl-1-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione

ID: ALA2368800

Cas Number: 101527-46-2

PubChem CID: 130510

Max Phase: Preclinical

Molecular Formula: C10H12F2N2O5

Molecular Weight: 278.21

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1[nH]c(=O)n([C@H]2C[C@H](O)[C@@H](CO)O2)cc1C(F)F

Standard InChI:  InChI=1S/C10H12F2N2O5/c11-8(12)4-2-14(10(18)13-9(4)17)7-1-5(16)6(3-15)19-7/h2,5-8,15-16H,1,3H2,(H,13,17,18)/t5-,6+,7+/m0/s1

Standard InChI Key:  YATQDPXPMDMPID-RRKCRQDMSA-N

Molfile:  

     RDKit          2D

 19 20  0  0  1  0  0  0  0  0999 V2000
    2.0482   -1.6716    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7127   -2.4253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1976   -3.0927    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3536   -2.2528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5633   -1.0041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0181   -3.0065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8687   -1.5853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8183   -0.2195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7383   -1.0041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1508    0.2654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1741   -2.1665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4834   -0.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8922   -2.5115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5030   -3.6739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6591   -2.8340    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.5097   -1.4129    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3012    0.0354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1508    1.0904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4364    1.5029    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  5  1  0
  5  9  1  0
 10  8  1  0
 11  4  1  0
 12  9  1  0
 13  2  2  0
 14  6  2  0
 15 11  1  0
 16 11  1  0
 12 17  1  6
 10 18  1  1
 19 18  1  0
  3  6  1  0
 10 12  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2368800

   alpha,alpha-Difluorothymidine

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: 278.21

Molecular Weight (Monoisotopic): 278.0714

AlogP: -0.89

#Rotatable Bonds: 3

Polar Surface Area: 104.55

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.99

CX Basic pKa: ┄

CX LogP: -1.24

CX LogD: -1.25

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.67

Np Likeness Score: 0.42

References

1. Matulic-Adamic J, Takahashi K, Chou TC, Gadler H, Price RW, Reddy AR, Kalman TI, Watanabe KA..  (1988)  Nucleosides. 150. Synthesis and some biological properties of 5-monofluoromethyl, 5-difluoromethyl, and 5-trifluoromethyl derivatives of 2'-deoxyuridine and 2'-deoxy-2'-fluoro-beta-D-arabinofuranosyluracil.,  31  (8): [PMID:2840503] [10.1021/jm00403a026]

Source

Source(1):

• Scientific Literature