4-propynyl-1-beta-d-ribofuranosylpyrazole-3-carboxamide

ID: ALA402062

PubChem CID: 24755066

Max Phase: Preclinical

Molecular Formula: C12H15N3O5

Molecular Weight: 281.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC#Cc1cn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)nc1C(N)=O

Standard InChI:  InChI=1S/C12H15N3O5/c1-2-3-6-4-15(14-8(6)11(13)19)12-10(18)9(17)7(5-16)20-12/h4,7,9-10,12,16-18H,5H2,1H3,(H2,13,19)/t7-,9-,10-,12-/m1/s1

Standard InChI Key:  YOKKTTCOJDMJCZ-UGKPPGOTSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  1  0  0  0  0  0999 V2000
   12.5492  -14.7618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3742  -14.7618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6299  -13.9779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9617  -13.4904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2999  -13.9779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4151  -13.7225    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0846  -14.2132    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7552  -13.7257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4997  -12.9446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6747  -12.9430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5393  -13.9844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1527  -13.4326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5109  -13.7213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8990  -14.2748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9858  -12.2759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8577  -15.4281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0631  -15.4263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7100  -14.7908    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4718  -11.6073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9569  -10.9400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  3  6  1  1
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  6  1  0
  8 11  1  0
 11 12  2  0
  5 13  1  1
 13 14  1  0
  9 15  1  0
 15 19  3  0
  1  2  1  0
  2  3  1  0
  1 17  1  6
  2 16  1  6
 11 18  1  0
 19 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA402062

   1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-prop-1-ynylpyrazole-3-carboxamide

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: 281.27

Molecular Weight (Monoisotopic): 281.1012

AlogP: -2.04

#Rotatable Bonds: 3

Polar Surface Area: 130.83

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.30

CX Basic pKa: ┄

CX LogP: -1.16

CX LogD: -1.16

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.47

Np Likeness Score: 0.83

References

1. Moriyama K, Suzuki T, Negishi K, Graci JD, Thompson CN, Cameron CE, Watanabe M..  (2008)  Effects of introduction of hydrophobic group on ribavirin base on mutation induction and anti-RNA viral activity.,  51  (1): [PMID:18067241] [10.1021/jm7009952]

Source

Source(1):

• Scientific Literature