5-(2,3,5-trifluorophenyl)-1,4,5,6-tetrahydrocyclopenta[c]pyrazole-3-carboxylic acid

ID: ALA1208923

PubChem CID: 12003490

Max Phase: Preclinical

Molecular Formula: C13H9F3N2O2

Molecular Weight: 282.22

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1n[nH]c2c1CC(c1cc(F)cc(F)c1F)C2

Standard InChI:  InChI=1S/C13H9F3N2O2/c14-6-3-7(11(16)9(15)4-6)5-1-8-10(2-5)17-18-12(8)13(19)20/h3-5H,1-2H2,(H,17,18)(H,19,20)

Standard InChI Key:  RLMNVSLAEYDKEG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
   -1.5126  -10.5205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6875  -10.5209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7651   -9.7367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2419   -9.2516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0132   -8.4622    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8428   -8.4613    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1000   -9.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4294   -9.7384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9609   -9.6562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9700  -10.4811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6708   -9.2359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9289  -11.2295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7550  -11.2234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1714  -11.9347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7629  -12.6525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9337  -12.6545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5209  -11.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6959  -11.9451    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5227  -13.3699    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9964  -11.9296    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  9 10  1  0
  9 11  2  0
  5  6  1  0
  2  8  1  0
 12 13  2  0
  7  3  1  0
 13 14  1  0
  3  1  1  0
 14 15  2  0
  4  5  2  0
 15 16  1  0
  6  7  1  0
 16 17  2  0
 17 12  1  0
  1 12  1  0
  8  4  1  0
 17 18  1  0
  7  8  2  0
 16 19  1  0
  4  9  1  0
 14 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1208923

   5-(2,3,5-Trifluorophenyl)-1,4,5,6-tetrahydrocyclopenta[c]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: 282.22

Molecular Weight (Monoisotopic): 282.0616

AlogP: 2.41

#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: 3.16

CX Basic pKa: 0.29

CX LogP: 2.94

CX LogD: -0.51

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.83

Np Likeness Score: -1.13

References

1. Imbriglio JE, Chang S, Liang R, Raghavan S, Schmidt D, Smenton A, Tria S, Schrader TO, Jung JK, Esser C, Holt TG, Wolff MS, Taggart AK, Cheng K, Carballo-Jane E, Waters MG, Tata JR, Colletti SL..  (2010)  GPR109a agonists. Part 2: pyrazole-acids as agonists of the human orphan G-protein coupled receptor GPR109a.,  20  (15): [PMID:20615702] [10.1016/j.bmcl.2010.06.041]

Source

Source(1):

• Scientific Literature