1,4,5,6-Tetrahydro-cyclopentapyrazole-3-carboxylic acid

ID: ALA128604

Cas Number: 5932-32-1

PubChem CID: 776416

Product Number: C185444, Order Now?

Max Phase: Preclinical

Molecular Formula: C7H8N2O2

Molecular Weight: 152.15

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1n[nH]c2c1CCC2

Standard InChI:  InChI=1S/C7H8N2O2/c10-7(11)6-4-2-1-3-5(4)8-9-6/h1-3H2,(H,8,9)(H,10,11)

Standard InChI Key:  FCYBBDFUBSEGMX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 11 12  0  0  0  0  0  0  0  0999 V2000
   -3.4203    0.2860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4363    1.6220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9105    0.9481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6464    1.3751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6387    0.5501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8516    0.3023    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3728    0.9744    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8640    1.6373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6203    2.4245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8149    2.6035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1780    3.0324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  1  0
  2  3  1  0
  3  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  4  1  0
  4  5  2  0
  1  5  1  0
  9 10  1  0
  9 11  2  0
  8  9  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA128604

   Cyclopentapyrazole-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: 152.15

Molecular Weight (Monoisotopic): 152.0586

AlogP: 0.60

#Rotatable Bonds: 1

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: 3.17

CX Basic pKa: 0.33

CX LogP: 1.09

CX LogD: -2.36

Aromatic Rings: 1

Heavy Atoms: 11

QED Weighted: 0.62

Np Likeness Score: -1.48

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. Semple G, Skinner PJ, Gharbaoui T, Shin YJ, Jung JK, Cherrier MC, Webb PJ, Tamura SY, Boatman PD, Sage CR, Schrader TO, Chen R, Colletti SL, Tata JR, Waters MG, Cheng K, Taggart AK, Cai TQ, Carballo-Jane E, Behan DP, Connolly DT, Richman JG..  (2008)  3-(1H-tetrazol-5-yl)-1,4,5,6-tetrahydro-cyclopentapyrazole (MK-0354): a partial agonist of the nicotinic acid receptor, G-protein coupled receptor 109a, with antilipolytic but no vasodilatory activity in mice.,  51  (16): [PMID:18665582] [10.1021/jm800258p]

4. Boatman PD, Richman JG, Semple G..  (2008)  Nicotinic acid receptor agonists.,  51  (24): [PMID:18983141] [10.1021/jm800896z]

5. Chen Y, Shoichet BK..  (2009)  Molecular docking and ligand specificity in fragment-based inhibitor discovery.,  5  (5): [PMID:19305397] [10.1038/nchembio.155]

Source

Source(1):

• Scientific Literature