1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-imidazo[1,2-b]pyrazole-7-carbonitrile

ID: ALA1939689

PubChem CID: 21603711

Max Phase: Preclinical

Molecular Formula: C11H12N4O4

Molecular Weight: 264.24

Molecule Type: Small molecule

Names and Identifiers

Synonyms: NSC-370383 | NSC-370383|CHEMBL1939689|JCZLDSSPTGHSFZ-TURQNECASA-N|1-.beta.-d-Ribofuranosylimidazo[1,2-b]pyrazole-7-carbonitrile

Canonical SMILES:  N#Cc1cnn2ccn([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)c12

Standard InChI:  InChI=1S/C11H12N4O4/c12-3-6-4-13-15-2-1-14(10(6)15)11-9(18)8(17)7(5-16)19-11/h1-2,4,7-9,11,16-18H,5H2/t7-,8-,9-,11-/m1/s1

Standard InChI Key:  JCZLDSSPTGHSFZ-TURQNECASA-N

Molfile:  

     RDKit          2D

 19 21  0  0  0  0  0  0  0  0999 V2000
    7.7464   -7.9846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0522   -7.5330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3177   -7.9088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5833   -7.5330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9995   -8.1168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3752   -8.8513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9995   -9.5900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1889   -8.7224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7728   -9.3063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1858   -7.9879    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8100   -7.2534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9963   -7.3823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8675   -8.1960    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836   -8.7798    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6595   -9.5184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4731   -9.3855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -8.5718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0569   -9.9693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6407  -10.5531    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  6
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  1
  6  8  1  0
  3  8  1  0
  8  9  1  1
  5 10  1  6
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 10 17  1  0
 13 17  1  0
 16 18  1  0
 18 19  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA1939689

   1-beta-d-Ribofuranosylimidazo[1,2-b]pyrazole-7-carbonitrile

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: 264.24

Molecular Weight (Monoisotopic): 264.0859

AlogP: -1.38

#Rotatable Bonds: 2

Polar Surface Area: 115.94

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.46

CX Basic pKa: ┄

CX LogP: -0.84

CX LogD: -0.84

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.62

Np Likeness Score: 0.16

References

1. Wang Y, Hess TN, Jones V, Zhou JZ, McNeil MR, Andrew McCammon J..  (2011)  Novel inhibitors of Mycobacterium tuberculosis dTDP-6-deoxy-L-lyxo-4-hexulose reductase (RmlD) identified by virtual screening.,  21  (23): [PMID:22014548] [10.1016/j.bmcl.2011.09.094]

Source

Source(1):

• Scientific Literature