(R)-5-fluoro-2-hydroxy-4-(N-(4-isopropylbenzyl)-1-(perfluorophenylsulfonyl)azetidine-2-carboxamido)benzoic acid

ID: ALA4796668

PubChem CID: 135257626

Max Phase: Preclinical

Molecular Formula: C27H22F6N2O6S

Molecular Weight: 616.54

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)c1ccc(CN(C(=O)[C@H]2CCN2S(=O)(=O)c2c(F)c(F)c(F)c(F)c2F)c2cc(O)c(C(=O)O)cc2F)cc1

Standard InChI:  InChI=1S/C27H22F6N2O6S/c1-12(2)14-5-3-13(4-6-14)11-34(18-10-19(36)15(27(38)39)9-16(18)28)26(37)17-7-8-35(17)42(40,41)25-23(32)21(30)20(29)22(31)24(25)33/h3-6,9-10,12,17,36H,7-8,11H2,1-2H3,(H,38,39)/t17-/m1/s1

Standard InChI Key:  SELLKXQAKJSBIR-QGZVFWFLSA-N

Molfile:  

 
     RDKit          2D

 42 45  0  0  0  0  0  0  0  0999 V2000
   34.3303  -17.8172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.9122  -18.3992    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   35.1252  -17.6042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.5213  -18.9811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5213  -19.7983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3385  -19.7983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3385  -18.9811    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.7057  -18.6148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9136  -19.4052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7021  -19.6168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2809  -19.0387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0657  -18.2459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2776  -18.0380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9435  -18.4032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1550  -17.6139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.1541  -18.6148    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.0629  -17.2495    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   35.3343  -19.9816    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   37.6415  -17.6661    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   38.0705  -19.2491    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   36.9132  -20.4063    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   31.5763  -18.0369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7869  -18.2484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2130  -17.6679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4243  -17.8788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2122  -18.6689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7949  -19.2479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5814  -19.0339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9426  -19.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1529  -19.6108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9413  -20.3993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5194  -20.9781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3122  -20.7629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5201  -19.9748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3103  -21.7698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5213  -21.9823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.8889  -22.3468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.8921  -21.3387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.4231  -18.8815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8445  -18.3044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2127  -19.6711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1482  -18.7913    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  4  1  0
  7  2  1  0
  2  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
  4 14  1  6
 14 15  2  0
 14 16  1  0
 13 17  1  0
  9 18  1  0
 12 19  1  0
 11 20  1  0
 10 21  1  0
 16 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 16 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 29  1  0
 35 36  1  0
 35 37  2  0
 32 35  1  0
 33 38  1  0
 26 39  1  0
 39 40  1  0
 39 41  1  0
 30 42  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4796668

   ---

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: 616.54

Molecular Weight (Monoisotopic): 616.1103

AlogP: 5.04

#Rotatable Bonds: 8

Polar Surface Area: 115.22

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 2.53

CX Basic pKa: ┄

CX LogP: 5.73

CX LogD: 2.22

Aromatic Rings: 3

Heavy Atoms: 42

QED Weighted: 0.21

Np Likeness Score: -0.97

References

1. Brotherton-Pleiss C,Yue P,Zhu Y,Nakamura K,Chen W,Fu W,Kubota C,Chen J,Alonso-Valenteen F,Mikhael S,Medina-Kauwe L,Tius MA,Lopez-Tapia F,Turkson J.  (2021)  Discovery of Novel Azetidine Amides as Potent Small-Molecule STAT3 Inhibitors.,  64  (1.0): [PMID:33352047] [10.1021/acs.jmedchem.0c01705]

Source

Source(1):

• Scientific Literature