2-(3-(5-chloro-2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)-3-azaspiro[5.5]undecan-9-yl)acetic acid

ID: ALA3937916

PubChem CID: 117886639

Max Phase: Preclinical

Molecular Formula: C22H30ClNO3

Molecular Weight: 391.94

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)Cc2cc(Cl)cc(N3CCC4(CCC(CC(=O)O)CC4)CC3)c2O1

Standard InChI:  InChI=1S/C22H30ClNO3/c1-21(2)14-16-12-17(23)13-18(20(16)27-21)24-9-7-22(8-10-24)5-3-15(4-6-22)11-19(25)26/h12-13,15H,3-11,14H2,1-2H3,(H,25,26)

Standard InChI Key:  NUGWEZBZPNGBKL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   14.8706   -5.5434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1643   -5.9565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8752   -6.3617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4661   -5.5555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7495   -5.1452    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   12.8842  -10.5049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1817   -7.6140    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1835   -5.1382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8733  -12.1572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1611  -11.7393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8944   -8.8567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8674  -12.9830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4560  -10.4951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8906   -9.6777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1670  -10.9135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4691   -8.8567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1817   -6.7882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5913  -11.7494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8944   -8.0310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1780   -9.2654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4691   -8.0310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4607   -9.6741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4693   -6.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8992   -5.5519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9022   -6.3738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6848   -6.6249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6800   -5.2952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
 10  9  1  0
 13 15  1  0
  8  4  1  0
 17 25  2  0
  6 14  1  0
 22 13  1  0
 20 11  1  0
 20 22  1  0
  9 18  1  0
 16 20  1  0
  4  5  1  0
 21  7  1  0
 19  7  1  0
 15 10  1  0
 20 14  1  0
  7 17  1  0
 11 19  1  0
 15  6  1  0
  9 12  2  0
 23 17  1  0
 24  8  2  0
 21 16  1  0
  4 23  2  0
 24 25  1  0
 25 26  1  0
 26  2  1  0
  2 27  1  0
 27 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3937916

   2-[3-(5-chloro-2,2-dimethyl-3H-1-benzofuran-7-yl)-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: 391.94

Molecular Weight (Monoisotopic): 391.1914

AlogP: 5.31

#Rotatable Bonds: 3

Polar Surface Area: 49.77

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.70

CX Basic pKa: 2.76

CX LogP: 4.87

CX LogD: 2.33

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.76

Np Likeness Score: 0.06

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