cis-N-(2-chloro-6-methylphenyl)-2-[[6-[4-[4-[4-[[4-[[2-(2,6-dioxo-3-piperidyl)-1-oxoisoindolin-4-yl]carbamoyl]phenyl]azo]phenoxy]butyl]piperazin-1-yl]-2-methylpyrimidin-4-yl]amino]thiazole-5-carboxamide

ID: ALA4593817

Max Phase: Preclinical

Molecular Formula: C50H49ClN12O6S

Molecular Weight: 981.54

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1nc(Nc2ncc(C(=O)Nc3c(C)cccc3Cl)s2)cc(N2CCN(CCCCOc3ccc(/N=N\c4ccc(C(=O)Nc5cccc6c5CN(C5CCC(=O)NC5=O)C6=O)cc4)cc3)CC2)n1

Standard InChI:  InChI=1S/C50H49ClN12O6S/c1-30-7-5-9-38(51)45(30)58-48(67)41-28-52-50(70-41)56-42-27-43(54-31(2)53-42)62-24-22-61(23-25-62)21-3-4-26-69-35-17-15-34(16-18-35)60-59-33-13-11-32(12-14-33)46(65)55-39-10-6-8-36-37(39)29-63(49(36)68)40-19-20-44(64)57-47(40)66/h5-18,27-28,40H,3-4,19-26,29H2,1-2H3,(H,55,65)(H,58,67)(H,57,64,66)(H,52,53,54,56)/b60-59-

Standard InChI Key:  DYBUXZNKVNIICM-BOIJWLLJSA-N

Molfile:  

 
     RDKit          2D

 70 78  0  0  0  0  0  0  0  0999 V2000
   25.1520  -23.9226    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.4372  -24.3346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1526  -23.0976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4385  -22.6846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7231  -23.9215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7237  -23.0965    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.0095  -22.6835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0143  -21.8599    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.3009  -21.4470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5852  -21.8589    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.5872  -22.6882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3010  -23.0974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3020  -20.6220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8738  -23.1026    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.1583  -22.6920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0713  -21.8717    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.2638  -21.7024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8532  -22.4179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4070  -23.0294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.9261  -20.9496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4093  -20.2808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1055  -20.8656    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7679  -20.1129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2522  -19.4420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9152  -18.6898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0937  -18.6053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9498  -20.0286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5292  -19.3101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5033  -20.7222    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   19.0729  -19.5260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4482  -23.0997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4471  -23.9313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1661  -24.3483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8866  -23.9307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8838  -23.0961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1643  -22.6870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7281  -24.3473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.6009  -22.6809    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.0098  -23.9301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2942  -24.3407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5809  -23.9264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8653  -24.3370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3158  -23.0925    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.3168  -23.9175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6013  -24.3280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6019  -25.1522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3174  -25.5646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0337  -25.1468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0296  -24.3240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3196  -26.3896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6061  -26.8039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.0350  -26.8003    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.0371  -27.6253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3220  -28.0374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3237  -28.8617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0398  -29.2732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7503  -28.0315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7560  -28.8524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5385  -29.1006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0165  -28.4330    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.5292  -27.7724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8399  -28.4249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2562  -29.1383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0776  -29.1344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4889  -28.4189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0726  -27.7055    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.2450  -27.7078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7990  -29.8834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.8281  -26.9957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.3138  -28.4162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  0
  3  4  1  0
  2  5  1  0
  5  6  1  0
  6  4  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
  9 13  1  0
 11 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 15  2  0
 17 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 28  1  0
 27 23  1  0
 27 28  2  0
 27 29  1  0
 24 30  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  2  0
 36 31  1  0
 32 37  1  0
 35 38  1  0
 37 39  1  0
 39 40  1  0
 40 41  1  0
 41 42  1  0
 42  1  1  0
 38 43  2  0
 43 44  1  0
 44 45  2  0
 45 46  1  0
 46 47  2  0
 47 48  1  0
 48 49  2  0
 49 44  1  0
 47 50  1  0
 50 51  2  0
 50 52  1  0
 52 53  1  0
 53 54  2  0
 54 55  1  0
 55 56  2  0
 56 58  1  0
 57 53  1  0
 57 58  2  0
 58 59  1  0
 59 60  1  0
 60 61  1  0
 61 57  1  0
 62 63  1  0
 62 67  1  0
 63 64  1  0
 64 65  1  0
 65 66  1  0
 66 67  1  0
 60 62  1  0
 59 68  2  0
 67 69  2  0
 65 70  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4593817

   ---

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: 981.54

Molecular Weight (Monoisotopic): 980.3307

AlogP: 8.61

#Rotatable Bonds: 16

Polar Surface Area: 215.81

Molecular Species: BASE

HBA: 15

HBD: 4

#RO5 Violations: 3

HBA (Lipinski): 18

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 8.49

CX Basic pKa: 8.59

CX LogP: 8.06

CX LogD: 7.79

Aromatic Rings: 6

Heavy Atoms: 70

QED Weighted: 0.04

Np Likeness Score: -1.38

References

1. Jin YH, Lu MC, Wang Y, Shan WX, Wang XY, You QD, Jiang ZY..  (2020)  Azo-PROTAC: Novel Light-Controlled Small-Molecule Tool for Protein Knockdown.,  63  (9): [PMID:32153174] [10.1021/acs.jmedchem.9b02058]

Source

Source(1):

• Scientific Literature