5-(3-Chloro-benzyl)-1H-pyrazole-3-carboxylic acid

ID: ALA394441

Cas Number: 595610-55-2

PubChem CID: 11776293

Max Phase: Preclinical

Molecular Formula: C11H9ClN2O2

Molecular Weight: 236.66

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1cc(Cc2cccc(Cl)c2)n[nH]1

Standard InChI:  InChI=1S/C11H9ClN2O2/c12-8-3-1-2-7(4-8)5-9-6-10(11(15)16)14-13-9/h1-4,6H,5H2,(H,13,14)(H,15,16)

Standard InChI Key:  UYMDSFKYOCEPFN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 16 17  0  0  0  0  0  0  0  0999 V2000
    8.3541   -0.7625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1791   -0.7625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4359    0.0216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7666    0.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1016    0.0216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2243    0.2774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8366   -0.2755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3970    1.0841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3169    0.2762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1450    1.0831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7597    1.6345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5883    2.4407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8029    2.6960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1887    2.1389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3632    1.3347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2014    2.9927    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  3  6  1  0
  3  4  2  0
  5  9  1  0
  4  5  1  0
  9 10  1  0
  5  1  2  0
 10 11  2  0
  1  2  1  0
 11 12  1  0
 12 13  2  0
  2  3  1  0
 13 14  1  0
  6  7  1  0
 14 15  2  0
 15 10  1  0
  6  8  2  0
 12 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA394441

   5-(3-Chlorobenzyl)-1H-pyrazole-3-carboxylic acid

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: 236.66

Molecular Weight (Monoisotopic): 236.0353

AlogP: 2.35

#Rotatable Bonds: 3

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: 3.54

CX Basic pKa: 1.73

CX LogP: 2.25

CX LogD: -0.95

Aromatic Rings: 2

Heavy Atoms: 16

QED Weighted: 0.86

Np Likeness Score: -1.33

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. 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]

3. Richman JG, Kanemitsu-Parks M, Gaidarov I, Cameron JS, Griffin P, Zheng H, Guerra NC, Cham L, Maciejewski-Lenoir D, Behan DP, Boatman D, Chen R, Skinner P, Ornelas P, Waters MG, Wright SD, Semple G, Connolly DT..  (2007)  Nicotinic acid receptor agonists differentially activate downstream effectors.,  282  (25): [PMID:17452318] [10.1074/jbc.m701866200]

Source

Source(1):

• Scientific Literature