sodium (R)-4-(N-(4-cyclohexylbenzyl)-1-(perfluorophenylsulfonyl)azetidine-2-carboxamido)-5-fluoro-2-hydroxybenzoate

ID: ALA4752153

PubChem CID: 153301490

Max Phase: Preclinical

Molecular Formula: C30H25F6N2NaO6S

Molecular Weight: 656.60

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C([O-])c1cc(F)c(N(Cc2ccc(C3CCCCC3)cc2)C(=O)[C@H]2CCN2S(=O)(=O)c2c(F)c(F)c(F)c(F)c2F)cc1O.[Na+]

Standard InChI:  InChI=1S/C30H26F6N2O6S.Na/c31-19-12-18(30(41)42)22(39)13-21(19)37(14-15-6-8-17(9-7-15)16-4-2-1-3-5-16)29(40)20-10-11-38(20)45(43,44)28-26(35)24(33)23(32)25(34)27(28)36;/h6-9,12-13,16,20,39H,1-5,10-11,14H2,(H,41,42);/q;+1/p-1/t20-;/m1./s1

Standard InChI Key:  UVRXFONKVVRODZ-VEIFNGETSA-M

Molfile:  

     RDKit          2D

 46 49  0  0  0  0  0  0  0  0999 V2000
   28.8122  -13.3309    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
   33.5585   -8.9767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.1404   -9.5587    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
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   33.5667  -10.9578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5667  -10.1406    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.9339   -9.7742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1418  -10.5647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9303  -10.7763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5091  -10.1982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2939   -9.4054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5058   -9.1975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1717   -9.5627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3832   -8.7734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.3823   -9.7742    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   30.8045   -9.1964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0152   -9.4079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4412   -8.8273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6525   -9.0383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   29.0231  -10.4074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8096  -10.1934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1708  -10.5636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   30.1695  -11.5588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7477  -12.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5404  -11.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7483  -11.1343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5385  -12.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7495  -13.1418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.1171  -13.5063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.1203  -12.4982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.3764   -9.9507    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   27.6564  -10.0414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0785   -9.4622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2924   -9.6720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0777  -10.4608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6556  -11.0400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4482  -10.8302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0
  4  3  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  5  1  0
  8  3  1  0
  3  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
  5 15  1  6
 15 16  2  0
 15 17  1  0
 14 18  1  0
 10 19  1  0
 13 20  1  0
 12 21  1  0
 11 22  1  0
 17 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
 17 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 30  1  0
 36 37  1  0
 36 38  2  0
 33 36  1  0
 34 39  1  0
 31 40  1  0
 41 42  1  0
 41 46  1  0
 42 43  1  0
 43 44  1  0
 44 45  1  0
 45 46  1  0
 27 41  1  0
M  CHG  2   1   1  37  -1
M  END

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: 656.60

Molecular Weight (Monoisotopic): 656.1416

AlogP: 5.97

#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: 6.60

CX LogD: 3.09

Aromatic Rings: 3

Heavy Atoms: 45

QED Weighted: 0.18

Np Likeness Score: -0.88

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