4-phenylethynyl-1-beta-D-ribofuranosylpyrazole-3-carboxamide

ID: ALA428058

PubChem CID: 24754989

Max Phase: Preclinical

Molecular Formula: C17H17N3O5

Molecular Weight: 343.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(=O)c1nn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)cc1C#Cc1ccccc1

Standard InChI:  InChI=1S/C17H17N3O5/c18-16(24)13-11(7-6-10-4-2-1-3-5-10)8-20(19-13)17-15(23)14(22)12(9-21)25-17/h1-5,8,12,14-15,17,21-23H,9H2,(H2,18,24)/t12-,14-,15-,17-/m1/s1

Standard InChI Key:  IXSVQAIOCGFUJM-DNNBLBMLSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  1  0  0  0  0  0999 V2000
   -3.1216  -21.3118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2966  -21.3118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0409  -20.5279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7091  -20.0404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3709  -20.5279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2557  -20.2725    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5863  -20.7632    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0844  -20.2757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1711  -19.4946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9961  -19.4930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8685  -20.5344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4819  -19.9826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1599  -20.2713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7718  -20.8248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3149  -18.8259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8010  -18.1573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2861  -17.4900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1046  -17.5817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5895  -16.9152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2542  -16.1605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4292  -16.0763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9479  -16.7437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8131  -21.9781    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6077  -21.9763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0392  -21.3408    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  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 16  3  0
 16 17  1  0
  1  2  1  0
 17 18  2  0
  2  3  1  0
 18 19  1  0
  3  4  1  0
 19 20  2  0
  4  5  1  0
 20 21  1  0
  5  1  1  0
 21 22  2  0
 22 17  1  0
  3  6  1  1
  1 24  1  6
  2 23  1  6
 11 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA428058

   1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-(2-phenylethynyl)pyrazole-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: 343.34

Molecular Weight (Monoisotopic): 343.1168

AlogP: -1.01

#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: 12.29

CX Basic pKa: ┄

CX LogP: -0.02

CX LogD: -0.02

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.53

Np Likeness Score: 0.12

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