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

ID: ALA4483734

PubChem CID: 155540844

Max Phase: Preclinical

Molecular Formula: C11H14ClN3O6

Molecular Weight: 319.70

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@@]1(O)[C@H](O)[C@@H](CO)O[C@H]1n1cc(Cl)nc(C(N)=O)c1=O

Standard InChI:  InChI=1S/C11H14ClN3O6/c1-11(20)7(17)4(3-16)21-10(11)15-2-5(12)14-6(8(13)18)9(15)19/h2,4,7,10,16-17,20H,3H2,1H3,(H2,13,18)/t4-,7-,10-,11-/m1/s1

Standard InChI Key:  MCCKWXKHSAYRAW-HHXMPLFPSA-N

Molfile:  

 
     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
    4.7273  -26.2030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4963  -27.3883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7905  -26.9797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0490  -26.2030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9774  -26.9797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3860  -25.7209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7561  -25.7934    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7561  -24.9762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4614  -26.1979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1666  -25.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1666  -24.9762    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4614  -24.5635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4614  -27.0151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4962  -27.6402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3118  -26.2030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0196  -25.7944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7864  -27.7969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8738  -26.2030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5821  -25.7954    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8726  -27.0202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4614  -23.7463    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0
  3  4  1  0
  4  6  1  0
  6  1  1  0
  1  5  1  0
  4  7  1  1
  8  7  1  0
  8 12  2  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
  9 13  2  0
  3  2  1  1
  5 14  1  6
 15 16  1  0
  1 16  1  1
  3 17  1  0
 10 18  1  0
 18 19  1  0
 18 20  2  0
 12 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4483734

   ---

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: 319.70

Molecular Weight (Monoisotopic): 319.0571

AlogP: -2.00

#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: 12.43

CX Basic pKa: ┄

CX LogP: -1.78

CX LogD: -1.78

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.50

Np Likeness Score: 0.81

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