5-fluoro-1-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)pyrimidine-2,4(1H,3H)-dione

ID: ALA4081944

PubChem CID: 10708745

Max Phase: Preclinical

Molecular Formula: C10H13FN2O7

Molecular Weight: 292.22

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C10H13FN2O7/c11-3-1-13(10(19)12-8(3)18)9-7(17)6(16)5(15)4(2-14)20-9/h1,4-7,9,14-17H,2H2,(H,12,18,19)/t4-,5-,6+,7-,9-/m1/s1

Standard InChI Key:  YHWGRVDTEORPPJ-XSEHCYKFSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
   25.8536   -3.4146    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.8536   -5.0539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.4332   -5.8737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0168   -5.0540    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.4331   -3.4146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3939   -3.9436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.1475   -3.8223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1475   -4.6420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4331   -5.0540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7271   -4.6421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7271   -3.8224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0168   -3.4147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5580   -3.8242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2620   -3.4199    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.2661   -2.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5601   -2.1944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8499   -2.6003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5558   -4.6414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.9754   -2.1982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.5628   -1.3772    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  6 12  1  0
 11  5  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  1
  7  1  1  1
  8  2  1  6
  9  3  1  1
 10  4  1  6
  1 13  1  0
  1 17  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 13 18  2  0
 15 19  2  0
 16 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4081944

   5-Fluoro-1-(Beta-D-Glucopyranosyl)pyrimidine-2,4(1h,3h)-Dione

Molecule Features

Natural Product: Yes

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: 292.22

Molecular Weight (Monoisotopic): 292.0707

AlogP: -3.35

#Rotatable Bonds: 2

Polar Surface Area: 145.01

Molecular Species: NEUTRAL

HBA: 8

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.07

CX Basic pKa: ┄

CX LogP: -2.85

CX LogD: -2.93

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.38

Np Likeness Score: 0.95

References

1. Bokor É, Kyriakis E, Solovou TGA, Koppány C, Kantsadi AL, Szabó KE, Szakács A, Stravodimos GA, Docsa T, Skamnaki VT, Zographos SE, Gergely P, Leonidas DD, Somsák L..  (2017)  Nanomolar Inhibitors of Glycogen Phosphorylase Based on β-d-Glucosaminyl Heterocycles: A Combined Synthetic, Enzyme Kinetic, and Protein Crystallography Study.,  60  (22): [PMID:28925695] [10.1021/acs.jmedchem.7b01056]

Source

Source(1):

• Scientific Literature