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

ID: ALA397785

Cas Number: 5071-61-4

PubChem CID: 121025

Product Number: P160448, Order Now?

Max Phase: Preclinical

Molecular Formula: C10H8N2O2

Molecular Weight: 188.19

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1cc(-c2ccccc2)n[nH]1

Standard InChI:  InChI=1S/C10H8N2O2/c13-10(14)9-6-8(11-12-9)7-4-2-1-3-5-7/h1-6H,(H,11,12)(H,13,14)

Standard InChI Key:  QBPUOAJBMXXBNU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 14 15  0  0  0  0  0  0  0  0999 V2000
   15.0750  -28.4959    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9000  -28.4959    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1568  -27.7117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4875  -27.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8224  -27.7117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9451  -27.4559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5575  -28.0088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1178  -26.6492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0377  -27.4571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8691  -26.6515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0852  -26.3968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4714  -26.9494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6468  -27.7599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4305  -28.0108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0
  6  8  2  0
  3  6  1  0
  3  4  2  0
  5  9  1  0
  4  5  1  0
  9 10  2  0
  5  1  2  0
 10 11  1  0
  1  2  1  0
 11 12  2  0
 12 13  1  0
  2  3  1  0
 13 14  2  0
 14  9  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA397785

   3-Phenylpyrazole-5-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: 188.19

Molecular Weight (Monoisotopic): 188.0586

AlogP: 1.77

#Rotatable Bonds: 2

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: 3.50

CX Basic pKa: 1.25

CX LogP: 1.89

CX LogD: -1.49

Aromatic Rings: 2

Heavy Atoms: 14

QED Weighted: 0.75

Np Likeness Score: -1.32

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. PubChem BioAssay data set, 

4. PubChem BioAssay data set, 

5. Johansson NG, Turku A, Vidilaseris K, Dreano L, Khattab A, Ayuso Pérez D, Wilkinson A, Zhang Y, Tamminen M, Grazhdankin E, Kiriazis A, Fishwick CWG, Meri S, Yli-Kauhaluoma J, Goldman A, Boije Af Gennäs G, Xhaard H..  (2020)  Discovery of Membrane-Bound Pyrophosphatase Inhibitors Derived from an Isoxazole Fragment.,  11  (4): [PMID:32292570] [10.1021/acsmedchemlett.9b00537]

6. Messore A, Corona A, Madia VN, Saccoliti F, Tudino V, De Leo A, Scipione L, De Vita D, Amendola G, Di Maro S, Novellino E, Cosconati S, Métifiot M, Andreola ML, Valenti P, Esposito F, Grandi N, Tramontano E, Costi R, Di Santo R..  (2020)  Pyrrolyl Pyrazoles as Non-Diketo Acid Inhibitors of the HIV-1 Ribonuclease H Function of Reverse Transcriptase.,  11  (5): [PMID:32435387] [10.1021/acsmedchemlett.9b00617]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays