1-(2-Deoxy-2,2-difluoro-beta-D-erythro-pentofuranosyl)tetrahydro-2(1H)-pyrimidinone

ID: ALA3237553

PubChem CID: 57704511

Max Phase: Preclinical

Molecular Formula: C9H14F2N2O4

Molecular Weight: 252.22

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1NCCCN1[C@@H]1O[C@H](CO)[C@@H](O)C1(F)F

Standard InChI:  InChI=1S/C9H14F2N2O4/c10-9(11)6(15)5(4-14)17-7(9)13-3-1-2-12-8(13)16/h5-7,14-15H,1-4H2,(H,12,16)/t5-,6-,7-/m1/s1

Standard InChI Key:  MJVPVNQIMRZMTQ-FSDSQADBSA-N

Molfile:  

     RDKit          2D

 17 18  0  0  0  0  0  0  0  0999 V2000
    6.5238  -20.3397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6168  -21.1599    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.2807  -20.6693    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.2178  -21.0009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7000  -20.3421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4562  -19.5556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7725  -19.5355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1273  -19.0653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6721  -19.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6518  -18.4825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5603  -19.2791    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2708  -19.6948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9945  -19.2825    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9956  -18.4572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2809  -18.0421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5654  -18.4528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2730  -20.5155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  0
  5  1  1  0
  5  6  1  0
  1  7  1  0
  6  8  1  0
  7  8  1  0
  5  4  1  6
  9 10  1  0
  6  9  1  1
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 11  1  0
  7 11  1  1
 12 17  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3237553

   1-[(2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3-diazinan-2-one

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: 252.22

Molecular Weight (Monoisotopic): 252.0922

AlogP: -0.88

#Rotatable Bonds: 2

Polar Surface Area: 82.03

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.51

CX Basic pKa: ┄

CX LogP: -1.26

CX LogD: -1.26

Aromatic Rings: ┄

Heavy Atoms: 17

QED Weighted: 0.60

Np Likeness Score: 1.03

References

1. Ferraris D, Duvall B, Delahanty G, Mistry B, Alt J, Rojas C, Rowbottom C, Sanders K, Schuck E, Huang KC, Redkar S, Slusher BB, Tsukamoto T..  (2014)  Design, synthesis, and pharmacological evaluation of fluorinated tetrahydrouridine derivatives as inhibitors of cytidine deaminase.,  57  (6): [PMID:24520856] [10.1021/jm401856k]

Source

Source(1):

• Scientific Literature