(S)-2-Amino-N-(5-(6-chloro-5-((3-methylphenyl)sulfonamido)pyridin-3-yl)-4-methylthiazol-2-yl)-3-methylbutanamide

ID: ALA4174988

PubChem CID: 137333450

Max Phase: Preclinical

Molecular Formula: C21H24ClN5O3S2

Molecular Weight: 494.04

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cccc(S(=O)(=O)Nc2cc(-c3sc(NC(=O)[C@@H](N)C(C)C)nc3C)cnc2Cl)c1

Standard InChI:  InChI=1S/C21H24ClN5O3S2/c1-11(2)17(23)20(28)26-21-25-13(4)18(31-21)14-9-16(19(22)24-10-14)27-32(29,30)15-7-5-6-12(3)8-15/h5-11,17,27H,23H2,1-4H3,(H,25,26,28)/t17-/m0/s1

Standard InChI Key:  PIBKKQFQADCDAW-KRWDZBQOSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
   18.4116  -18.2093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0071  -18.9192    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.8241  -18.9146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7156  -20.1450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7144  -20.9645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4225  -21.3735    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.1321  -20.9640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1293  -20.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4207  -19.7361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8351  -19.7276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5829  -20.0572    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   22.1274  -19.4478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7161  -18.7416    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.9174  -18.9146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3081  -18.3701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9404  -19.5302    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.0078  -19.7365    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2998  -18.5109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3048  -17.6930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5979  -17.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8893  -17.6934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8921  -18.5149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5997  -18.9195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4182  -18.8672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2313  -18.9496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0830  -18.1219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.7091  -18.2867    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.0064  -21.3725    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   24.5665  -19.6949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0886  -20.3578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3795  -19.7772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5981  -16.4674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 10  2  0
  8 10  1  0
 14 15  1  0
 12 16  1  0
  4 17  1  0
 17  2  1  0
  2 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 16 24  1  0
 24 25  1  0
 24 26  2  0
 25 27  1  0
  5 28  1  0
 25 29  1  1
 29 30  1  0
 29 31  1  0
 20 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4174988

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 494.04

Molecular Weight (Monoisotopic): 493.1009

AlogP: 4.20

#Rotatable Bonds: 7

Polar Surface Area: 127.07

Molecular Species: BASE

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.26

CX Basic pKa: 8.96

CX LogP: 2.40

CX LogD: 2.36

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.42

Np Likeness Score: -1.79

References

1. Liang X, Li F, Chen C, Jiang Z, Wang A, Liu X, Ge J, Hu Z, Yu K, Wang W, Zou F, Liu Q, Wang B, Wang L, Zhang S, Wang Y, Liu Q, Liu J..  (2018)  Discovery of (S)-2-amino-N-(5-(6-chloro-5-(3-methylphenylsulfonamido)pyridin-3-yl)-4-methylthiazol-2-yl)-3-methylbutanamide (CHMFL-PI3KD-317) as a potent and selective phosphoinositide 3-kinase delta (PI3Kδ) inhibitor.,  156  [PMID:30053721] [10.1016/j.ejmech.2018.07.036]

Source

Source(1):

• Scientific Literature