1-(3-(4-Chloro-3,5-dimethylphenoxy)propyl)-3,5-dimethyl-4-(thiophen-2-ylsulfonyl)-1H-pyrrole-2-carboxylic acid

ID: ALA4866213

PubChem CID: 158543106

Max Phase: Preclinical

Molecular Formula: C22H24ClNO5S2

Molecular Weight: 482.02

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1cc(OCCCn2c(C)c(S(=O)(=O)c3cccs3)c(C)c2C(=O)O)cc(C)c1Cl

Standard InChI:  InChI=1S/C22H24ClNO5S2/c1-13-11-17(12-14(2)19(13)23)29-9-6-8-24-16(4)21(15(3)20(24)22(25)26)31(27,28)18-7-5-10-30-18/h5,7,10-12H,6,8-9H2,1-4H3,(H,25,26)

Standard InChI Key:  HOTQVQYCNRBOOE-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   17.6918   -9.1001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2834   -8.3876    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.8706   -9.0975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9900   -7.9599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7516   -8.2788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2895   -7.6533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8608   -6.9484    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.0580   -7.1384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1790   -6.1872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6788   -5.5311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9971   -4.7699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4969   -4.1138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8151   -3.3558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6307   -3.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9490   -2.4996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4514   -1.8447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6321   -1.9506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3175   -2.7078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1306   -1.2954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7692   -1.0866    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   20.7674   -2.3962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1118   -7.7207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4645   -8.4666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5814   -7.0424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9414   -9.0817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4325   -6.6004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5668   -7.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4747   -7.1534    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.6656   -6.9824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2531   -7.6992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8073   -8.3128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  4  5  1  0
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 13 14  2  0
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 16 20  1  0
 15 21  1  0
  6 22  1  0
 22 23  1  0
 22 24  2  0
  4  2  1  0
  5 25  1  0
  8 26  1  0
  2 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4866213

   ---

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: 482.02

Molecular Weight (Monoisotopic): 481.0784

AlogP: 5.44

#Rotatable Bonds: 8

Polar Surface Area: 85.60

Molecular Species: ACID

HBA: 6

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.24

CX Basic pKa: ┄

CX LogP: 5.80

CX LogD: 2.36

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.43

Np Likeness Score: -1.43

References

1. Zhu PJ, Yu ZZ, Lv YF, Zhao JL, Tong YY, You QD, Jiang ZY..  (2021)  Discovery of 3,5-Dimethyl-4-Sulfonyl-1H-Pyrrole-Based Myeloid Cell Leukemia 1 Inhibitors with High Affinity, Selectivity, and Oral Bioavailability.,  64  (15.0): [PMID:34342996] [10.1021/acs.jmedchem.1c00682]

Source

Source(1):

• Scientific Literature