6-benzyl-5-chloro-7-hydroxypyrazolo[1,5-a]pyrimidine-3-carbonitrile

ID: ALA2289489

PubChem CID: 53338872

Max Phase: Preclinical

Molecular Formula: C14H9ClN4O

Molecular Weight: 284.71

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1cnn2c(O)c(Cc3ccccc3)c(Cl)nc12

Standard InChI:  InChI=1S/C14H9ClN4O/c15-12-11(6-9-4-2-1-3-5-9)14(20)19-13(18-12)10(7-16)8-17-19/h1-5,8,20H,6H2

Standard InChI Key:  HOHNWEMSRSQMGQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
   19.1324  -21.8454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1313  -22.6649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8393  -23.0739    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.8375  -21.4365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5461  -21.8418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.5509  -22.6604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3310  -22.9088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8083  -22.2437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3232  -21.5843    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.8351  -20.6193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4232  -23.0730    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   18.4246  -21.4370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4244  -20.6198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1344  -20.2133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1346  -19.3969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4263  -18.9876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7163  -19.4008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7196  -20.2159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5897  -23.6810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8468  -24.4567    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  6  1  0
  5  4  1  0
  4  1  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  4 10  1  0
  2 11  1  0
  1 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 19 20  3  0
  7 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2289489

   5-Chloro-7-Hydroxy-6-(Phenylmethyl)pyrazolo[1,5-A]pyrimidine-3-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: 284.71

Molecular Weight (Monoisotopic): 284.0465

AlogP: 2.55

#Rotatable Bonds: 2

Polar Surface Area: 74.21

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.00

CX Basic pKa: ┄

CX LogP: 3.21

CX LogD: 1.98

Aromatic Rings: 3

Heavy Atoms: 20

QED Weighted: 0.73

Np Likeness Score: -1.47

References

1. Witschel M, Röhl F, Niggeweg R, Newton T..  (2013)  In search of new herbicidal inhibitors of the non-mevalonate pathway.,  69  (5): [PMID:23471898] [10.1002/ps.3479]

Source

Source(1):

• Scientific Literature