4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]pyrazolo[4,3-d]pyrimidin-3-yl]-3-fluoro-benzoic acid

ID: ALA4476096

PubChem CID: 155538306

Max Phase: Preclinical

Molecular Formula: C20H9ClF4N4O3

Molecular Weight: 464.76

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)c1ccc(-c2nn(C(=O)c3c(Cl)cccc3C(F)(F)F)c3cncnc23)c(F)c1

Standard InChI:  InChI=1S/C20H9ClF4N4O3/c21-12-3-1-2-11(20(23,24)25)15(12)18(30)29-14-7-26-8-27-17(14)16(28-29)10-5-4-9(19(31)32)6-13(10)22/h1-8H,(H,31,32)

Standard InChI Key:  YUVVZEHBMXMOCY-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   31.6228  -18.9027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1740  -17.0537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1728  -17.8732    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.8809  -18.2822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8791  -16.6448    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.5877  -17.0501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5879  -17.8732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3709  -18.1274    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.8546  -17.4613    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.3705  -16.7955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6266  -16.0188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4272  -15.8498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6796  -15.0733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1323  -14.4653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3295  -14.6389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0808  -15.4151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4230  -19.0742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6732  -19.8509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4718  -20.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0193  -19.4130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7628  -18.6326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9648  -18.4665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3836  -13.6876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1826  -13.5164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.8358  -13.0813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.0755  -19.5095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.7088  -17.6904    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   32.1256  -20.4574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3265  -20.2865    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   32.3771  -21.2350    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   31.7095  -21.1603    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   32.9736  -16.4574    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  7  2  0
  6  5  2  0
  5  2  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10  6  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
 10 11  1  0
  8  1  1  0
  1 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 14 23  1  0
 23 24  1  0
 23 25  2  0
  1 26  2  0
 22 27  1  0
 18 28  1  0
 28 29  1  0
 28 30  1  0
 28 31  1  0
 12 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4476096

   ---

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: 464.76

Molecular Weight (Monoisotopic): 464.0299

AlogP: 4.69

#Rotatable Bonds: 3

Polar Surface Area: 97.97

Molecular Species: ACID

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.57

CX Basic pKa: ┄

CX LogP: 4.25

CX LogD: 0.90

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.44

Np Likeness Score: -1.37

References

1. Zhang H, Lapointe BT, Anthony N, Azevedo R, Cals J, Correll CC, Daniels M, Deshmukh S, van Eenenaam H, Ferguson H, Hegde LG, Karstens WJ, Maclean J, Miller JR, Moy LY, Simov V, Nagpal S, Oubrie A, Palte RL, Parthasarathy G, Sciammetta N, van der Stelt M, Woodhouse JD, Trotter BW, Barr K..  (2020)  Discovery of N-(Indazol-3-yl)piperidine-4-carboxylic Acids as RORγt Allosteric Inhibitors for Autoimmune Diseases.,  11  (2): [PMID:32071676] [10.1021/acsmedchemlett.9b00431]

Source

Source(1):

• Scientific Literature