2-(3-(2-cyano-5-(trifluoromethoxy)phenyl)-3-azaspiro[5.5]undecan-9-yl)acetic acid

ID: ALA3973034

PubChem CID: 73777156

Max Phase: Preclinical

Molecular Formula: C20H23F3N2O3

Molecular Weight: 396.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1ccc(OC(F)(F)F)cc1N1CCC2(CCC(CC(=O)O)CC2)CC1

Standard InChI:  InChI=1S/C20H23F3N2O3/c21-20(22,23)28-16-2-1-15(13-24)17(12-16)25-9-7-19(8-10-25)5-3-14(4-6-19)11-18(26)27/h1-2,12,14H,3-11H2,(H,26,27)

Standard InChI Key:  SXNLLFZBIQFVNA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   11.4564   -5.5508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0216   -3.9058    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.7404   -5.1409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8733  -10.4960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8879   -6.3714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1714   -7.6076    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1732   -5.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8624  -12.1469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1508  -11.7294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8835   -8.8492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8565  -12.9720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4463  -10.4862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8797   -9.6695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1567  -10.9043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6018   -6.7852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4594   -8.8492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1714   -6.7825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5798  -11.7395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8883   -5.5472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8835   -8.0242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1677   -9.2576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7376   -4.3158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4594   -8.0242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4506   -3.9008    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.7301   -3.4908    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.4510   -9.6659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4596   -6.3738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3088   -7.1949    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
 12 14  1  0
  7  1  1  0
 22 25  1  0
 17  5  2  0
  4 13  1  0
 26 12  1  0
 21 10  1  0
 21 26  1  0
 22  2  1  0
  5 19  1  0
  8 18  1  0
 16 21  1  0
  1  3  1  0
 23  6  1  0
 20  6  1  0
 14  9  1  0
 21 13  1  0
  6 17  1  0
 10 20  1  0
 14  4  1  0
  8 11  2  0
 27 17  1  0
 22 24  1  0
  3 22  1  0
 19  7  2  0
  5 15  1  0
 23 16  1  0
  1 27  2  0
 15 28  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA3973034

   2-[3-[2-Cyano-5-(trifluoromethoxy)phenyl]-3-azaspiro[5.5]undecan-9-yl]acetic 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: 396.41

Molecular Weight (Monoisotopic): 396.1661

AlogP: 4.71

#Rotatable Bonds: 4

Polar Surface Area: 73.56

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.66

CX Basic pKa: 1.31

CX LogP: 5.09

CX LogD: 2.41

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.80

Np Likeness Score: -0.66

References

1. Cox JM, Chu HD, Chelliah MV, Debenham JS, Eagen K, Lan P, Lombardo M, London C, Plotkin MA, Shah U, Sun Z, Vaccaro HM, Venkatraman S, Suzuki T, Wang N, Ashley ER, Crespo A, Madeira M, Leung DH, Alleyne C, Ogawa AM, Souza S, Thomas-Fowlkes B, Di Salvo J, Weinglass A, Kirkland M, Pachanski M, Powles MA, Tozzo E, Akiyama TE, Ujjainwalla F, Tata JR, Sinz CJ..  (2017)  Design, Synthesis, and Evaluation of Novel and Selective G-protein Coupled Receptor 120 (GPR120) Spirocyclic Agonists.,  8  (1): [PMID:28105274] [10.1021/acsmedchemlett.6b00360]

Source

Source(1):

• Scientific Literature