(S)-2-(2,4-Dichloro-3-(2-cyclopropyl-5-methyl-4-(1-(trifluoromethyl)cyclopropyl)-1H-imidazole-1-yl)phenyl)-2-azaspiro[3.3]heptane-6-carboxylic Acid

ID: ALA4513808

PubChem CID: 155539171

Max Phase: Preclinical

Molecular Formula: C24H24Cl2F3N3O2

Molecular Weight: 514.38

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1c(C2(C(F)(F)F)CC2)nc(C2CC2)n1-c1c(Cl)ccc(N2CC3(CC(C(=O)O)C3)C2)c1Cl

Standard InChI:  InChI=1S/C24H24Cl2F3N3O2/c1-12-19(23(6-7-23)24(27,28)29)30-20(13-2-3-13)32(12)18-15(25)4-5-16(17(18)26)31-10-22(11-31)8-14(9-22)21(33)34/h4-5,13-14H,2-3,6-11H2,1H3,(H,33,34)

Standard InChI Key:  ATOAVZQFLCOJQE-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 34 39  0  0  0  0  0  0  0  0999 V2000
   29.2152  -21.0490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4152  -20.8324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1986  -21.6323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9986  -21.8490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2000  -19.9083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2042  -20.7333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9165  -20.3172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0710  -20.4583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.3565  -20.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3618  -19.2197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6481  -18.8073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9327  -19.2199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9353  -20.0492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6495  -20.4578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0777  -18.8096    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   33.1618  -21.2780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9688  -21.4495    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.3813  -20.7350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8292  -20.1220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9291  -20.8625    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   34.0012  -19.3152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2223  -20.4642    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.6181  -21.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4431  -21.4452    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   35.2071  -22.1623    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   36.0250  -22.1583    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   32.5511  -21.8345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7446  -22.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2984  -22.6198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4269  -20.2523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0139  -21.2606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4830  -22.0429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7696  -21.6285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.4808  -22.8679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  1  1  0
  6  5  1  0
  7  6  1  0
  5  7  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
 10 15  1  0
  8 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19  8  1  0
 14 20  1  0
 19 21  1  0
 18  6  1  0
 13 22  1  0
  6 23  1  0
 23 24  1  0
 23 25  1  0
 23 26  1  0
 28 27  1  0
 29 28  1  0
 27 29  1  0
 16 27  1  0
 22 30  1  0
 30  1  1  0
  1 31  1  0
 31 22  1  0
  3 32  1  0
 32 33  1  0
 32 34  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4513808

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 514.38

Molecular Weight (Monoisotopic): 513.1198

AlogP: 6.26

#Rotatable Bonds: 5

Polar Surface Area: 58.36

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.08

CX Basic pKa: 6.12

CX LogP: 4.44

CX LogD: 3.25

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.51

Np Likeness Score: -0.42

References

1. Hoegenauer K, Kallen J, Jiménez-Núñez E, Strang R, Ertl P, Cooke NG, Hintermann S, Voegtle M, Betschart C, McKay DJJ, Wagner J, Ottl J, Beerli C, Billich A, Dawson J, Kaupmann K, Streiff M, Gobeau N, Harlfinger S, Stringer R, Guntermann C..  (2019)  Structure-Based and Property-Driven Optimization of N-Aryl Imidazoles toward Potent and Selective Oral RORγt Inhibitors.,  62  (23): [PMID:31729873] [10.1021/acs.jmedchem.9b01291]

Source

Source(1):

• Scientific Literature