5-Butyl-1H-pyrazole-3-carboxylic acid

ID: ALA428730

Cas Number: 92933-48-7

PubChem CID: 6485181

Product Number: L287351, Order Now?

Max Phase: Preclinical

Molecular Formula: C8H12N2O2

Molecular Weight: 168.20

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCc1cc(C(=O)O)n[nH]1

Standard InChI:  InChI=1S/C8H12N2O2/c1-2-3-4-6-5-7(8(11)12)10-9-6/h5H,2-4H2,1H3,(H,9,10)(H,11,12)

Standard InChI Key:  ZJTXSGLJNBAMJS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 12 12  0  0  0  0  0  0  0  0999 V2000
    6.0727   -2.7907    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8793   -2.7907    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1279   -1.9600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4760   -1.4463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8241   -1.9600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8204   -1.5159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5228   -1.9478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8152   -0.6397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1224   -1.5205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4243   -1.9599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7273   -1.5185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0292   -1.9579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  6  1  0
  6  7  1  0
  2  3  2  0
  6  8  2  0
  3  4  1  0
  5  9  1  0
  4  5  2  0
  9 10  1  0
  5  1  1  0
 10 11  1  0
  1  2  1  0
 11 12  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA428730

   LUF 6283

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: 168.20

Molecular Weight (Monoisotopic): 168.0899

AlogP: 1.45

#Rotatable Bonds: 4

Polar Surface Area: 65.98

Molecular Species: ACID

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.19

CX Basic pKa: 0.39

CX LogP: 1.93

CX LogD: -1.52

Aromatic Rings: 1

Heavy Atoms: 12

QED Weighted: 0.71

Np Likeness Score: -0.91

References

1. van Herk T, Brussee J, van den Nieuwendijk AM, van der Klein PA, IJzerman AP, Stannek C, Burmeister A, Lorenzen A..  (2003)  Pyrazole derivatives as partial agonists for the nicotinic acid receptor.,  46  (18): [PMID:12930155] [10.1021/jm030888c]

2. Skinner PJ, Cherrier MC, Webb PJ, Shin YJ, Gharbaoui T, Lindstrom A, Hong V, Tamura SY, Dang HT, Pride CC, Chen R, Richman JG, Connolly DT, Semple G..  (2007)  Fluorinated pyrazole acids are agonists of the high affinity niacin receptor GPR109a.,  17  (20): [PMID:17804224] [10.1016/j.bmcl.2007.07.101]

3. Gharbaoui T, Skinner PJ, Shin YJ, Averbuj C, Jung JK, Johnson BR, Duong T, Decaire M, Uy J, Cherrier MC, Webb PJ, Tamura SY, Zou N, Rodriguez N, Boatman PD, Sage CR, Lindstrom A, Xu J, Schrader TO, Smith BM, Chen R, Richman JG, Connolly DT, Colletti SL, Tata JR, Semple G..  (2007)  Agonist lead identification for the high affinity niacin receptor GPR109a.,  17  (17): [PMID:17588745] [10.1016/j.bmcl.2007.06.028]

4. Maria Kuzikov, Elisa Costanzi, Jeanette Reinshagen, Francesca Esposito, Laura Vangeel, Markus Wolf, Bernhard Ellinger, Carsten Claussen, Gerd Geisslinger, Angela Corona, Daniela Iaconis, Carmine Talarico, Candida Manelfi, Rolando Cannalire, Giulia Rossetti, Jonas Gossen, Simone Albani, Francesco Musiani, Katja Herzog, Yang Ye, Barbara Giabbai, Nicola Demitri, Dirk Jochmans, Steven De Jonghe, Jasper Rymenants, Vincenzo Summa, Enzo Tramontano, Andrea R. Beccari, Pieter Leyssen, Paola Storici, Johan Neyts, Philip Gribbon, and Andrea Zaliani.  (2020)  Identification of inhibitors of SARS-Cov2 M-Pro enzymatic activity using a small molecule repurposing screen,  [10.6019/CHEMBL4495564]

5. Andrea Zaliani, Laura Vangeel, Jeanette Reinshagen, Daniela Iaconis, Maria Kuzikov, Oliver Keminer, Markus Wolf, Bernhard Ellinger, Francesca Esposito, Angela Corona, Enzo Tramontano, Candida Manelfi, Katja Herzog, Dirk Jochmans, Steven De Jonghe, Winston Chiu, Thibault Francken, Joost Schepers, Caroline Collard, Kayvan Abbasi, Carsten Claussen , Vincenzo Summa, Andrea R. Beccari, Johan Neyts, Philip Gribbon and Pieter Leyssen.  (2020)  Cytopathic SARS-Cov2 screening on VERO-E6 cells in a large repurposing effort,  [10.6019/CHEMBL4495565]

Source

Source(2):

• Scientific Literature
• SARS-CoV-2 Screening Data 2020-21