3-(1H-tetrazol-5-yl)-5-(2,3,5-trifluorophenyl)-1,4,5,6-tetrahydrocyclopenta[c]pyrazole

ID: ALA520137

PubChem CID: 12002618

Max Phase: Preclinical

Molecular Formula: C13H9F3N6

Molecular Weight: 306.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Fc1cc(F)c(F)c(C2Cc3[nH]nc(-c4nnn[nH]4)c3C2)c1

Standard InChI:  InChI=1S/C13H9F3N6/c14-6-3-7(11(16)9(15)4-6)5-1-8-10(2-5)17-18-12(8)13-19-21-22-20-13/h3-5H,1-2H2,(H,17,18)(H,19,20,21,22)

Standard InChI Key:  HJLIOQAZIYHNGR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 25  0  0  0  0  0  0  0  0999 V2000
    5.1868  -21.6136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6568  -22.2918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6865  -20.9572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4653  -21.2294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4461  -22.0515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2220  -22.3237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7208  -21.6700    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2530  -20.9938    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4585  -23.1141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9581  -23.7687    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4274  -24.4473    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2178  -24.2108    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2369  -23.3859    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3620  -21.5953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9707  -20.8699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1466  -20.8512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7174  -21.5569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1182  -22.2828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9411  -22.2980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6924  -22.9895    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.3412  -23.0195    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.7504  -20.1275    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  5  1  0
  4  3  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13  9  2  0
  3  1  1  0
  1 14  1  0
  5  6  1  0
 14 15  2  0
  6  7  2  0
 15 16  1  0
  7  8  1  0
 16 17  2  0
  8  4  1  0
 17 18  1  0
  4  5  2  0
 18 19  2  0
 19 14  1  0
  6  9  1  0
 18 20  1  0
  9 10  1  0
 19 21  1  0
  1  2  1  0
 16 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA520137

   3-(1H-tetrazol-5-yl)-5-(2,3,5-trifluorophenyl)-1,4,5,6-tetrahydrocyclopenta[c]pyrazole

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: 306.25

Molecular Weight (Monoisotopic): 306.0841

AlogP: 1.89

#Rotatable Bonds: 2

Polar Surface Area: 83.14

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.38

CX Basic pKa: 1.27

CX LogP: 2.56

CX LogD: 0.95

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.71

Np Likeness Score: -1.69

References

1. Imbriglio JE, Chang S, Liang R, Raghavan S, Schmidt D, Smenton A, Tria S, Schrader TO, Jung JK, Esser C, Taggart AK, Cheng K, Carballo-Jane E, Gerard Waters M, Tata JR, Colletti SL..  (2009)  GPR109a agonists. Part 1: 5-Alkyl and 5-aryl-pyrazole-tetrazoles as agonists of the human orphan G-protein coupled receptor GPR109a.,  19  (8): [PMID:19307116] [10.1016/j.bmcl.2009.03.014]

2. Imbriglio JE, Chang S, Liang R, Raghavan S, Schmidt D, Smenton A, Tria S, Schrader TO, Jung JK, Esser C, Taggart AK, Cheng K, Carballo-Jane E, Gerard Waters M, Tata JR, Colletti SL..  (2009)  GPR109a agonists. Part 1: 5-Alkyl and 5-aryl-pyrazole-tetrazoles as agonists of the human orphan G-protein coupled receptor GPR109a.,  19  (8): [PMID:19307116] [10.1016/j.bmcl.2009.03.014]

3. 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