(R)-4-(N-((5-cyclohexylpyrazin-2-yl)methyl)-1-(perfluorophenylsulfonyl)azetidine-2-carboxamido)-3-fluorobenzoic acid

ID: ALA4764704

PubChem CID: 150356586

Max Phase: Preclinical

Molecular Formula: C28H24F6N4O5S

Molecular Weight: 642.58

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)c1ccc(N(Cc2cnc(C3CCCCC3)cn2)C(=O)[C@H]2CCN2S(=O)(=O)c2c(F)c(F)c(F)c(F)c2F)c(F)c1

Standard InChI:  InChI=1S/C28H24F6N4O5S/c29-17-10-15(28(40)41)6-7-19(17)37(13-16-11-36-18(12-35-16)14-4-2-1-3-5-14)27(39)20-8-9-38(20)44(42,43)26-24(33)22(31)21(30)23(32)25(26)34/h6-7,10-12,14,20H,1-5,8-9,13H2,(H,40,41)/t20-/m1/s1

Standard InChI Key:  GUVNZKCDEKRDJY-HXUWFJFHSA-N

Molfile:  

 
     RDKit          2D

 44 48  0  0  0  0  0  0  0  0999 V2000
    9.6866  -18.1309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2685  -18.7129    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.4815  -17.9179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8776  -19.2948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8776  -20.1120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6948  -20.1120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6948  -19.2948    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0620  -18.9284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2699  -19.7189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0584  -19.9305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6372  -19.3524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4220  -18.5596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6339  -18.3517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2998  -18.7169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5113  -17.9276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5104  -18.9284    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4192  -17.5632    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.6906  -20.2952    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.9978  -17.9797    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.4268  -19.5628    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.2695  -20.7200    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.9326  -18.3506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1433  -18.5621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5694  -17.9815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7807  -18.1925    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5685  -18.9826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1512  -19.5616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9377  -19.3476    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2989  -19.7178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5093  -19.9244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2976  -20.7130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8758  -21.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6685  -21.0766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8764  -20.2885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6666  -22.0834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8776  -22.2960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2452  -22.6605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7781  -19.1955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2004  -18.6204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4129  -18.8305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1980  -19.6207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7769  -20.2008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5707  -19.9907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5045  -19.1049    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
 26 38  1  0
 38 39  1  0
 38 43  1  0
 39 40  1  0
 40 41  1  0
 41 42  1  0
 42 43  1  0
 30 44  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4764704

   ---

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: 642.58

Molecular Weight (Monoisotopic): 642.1372

AlogP: 5.05

#Rotatable Bonds: 8

Polar Surface Area: 120.77

Molecular Species: ACID

HBA: 6

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.85

CX Basic pKa: 0.65

CX LogP: 4.03

CX LogD: 0.79

Aromatic Rings: 3

Heavy Atoms: 44

QED Weighted: 0.21

Np Likeness Score: -1.11

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