4-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)-5-methyltetrahydrofuran-2-yl)-3-oxo-3,4-dihydropyrazine-2-carboxamide

ID: ALA4475484

PubChem CID: 155537688

Max Phase: Preclinical

Molecular Formula: C11H15N3O6

Molecular Weight: 285.26

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@]1(CO)O[C@@H](n2ccnc(C(N)=O)c2=O)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C11H15N3O6/c1-11(4-15)7(17)6(16)10(20-11)14-3-2-13-5(8(12)18)9(14)19/h2-3,6-7,10,15-17H,4H2,1H3,(H2,12,18)/t6-,7+,10-,11-/m1/s1

Standard InChI Key:  IWRTYUZXZWTJBK-LRMGWDNHSA-N

Molfile:  

 
     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
   16.0441   -3.7509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1074   -4.5276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3658   -3.7509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2943   -4.5276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7029   -3.2688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0729   -3.3413    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.0729   -2.5241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7782   -3.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4835   -3.3413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4835   -2.5241    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.7782   -2.1114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7782   -4.5629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8131   -5.1881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6287   -3.7509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3364   -3.3423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1906   -3.7509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1894   -4.5681    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.5854   -5.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3327   -4.1520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8989   -3.3433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  1  0
  2  3  1  0
  3  5  1  0
  5  1  1  0
  1  4  1  0
  3  6  1  1
  7  6  1  0
  7 11  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
  8 12  2  0
  4 13  1  6
 14 15  1  0
  1 15  1  1
  9 16  1  0
 16 17  1  0
  2 18  1  6
  1 19  1  0
 16 20  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4475484

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 285.26

Molecular Weight (Monoisotopic): 285.0961

AlogP: -2.66

#Rotatable Bonds: 3

Polar Surface Area: 147.90

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.49

CX Basic pKa: ┄

CX LogP: -2.45

CX LogD: -2.45

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.47

Np Likeness Score: 0.59

References

1. Guo S, Xu M, Guo Q, Zhu F, Jiang X, Xie Y, Shen J..  (2019)  Discovery of pyrimidine nucleoside dual prodrugs and pyrazine nucleosides as novel anti-HCV agents.,  27  (5): [PMID:30683552] [10.1016/j.bmc.2019.01.007]

Source

Source(1):

• Scientific Literature