4-((4-Bromophenyl)sulfonyl)-1-(3-(4-chloro-3,5-dimethylphenoxy)propyl)-3,5-dimethy-1H-pyrrole-2-carboxylic acid

ID: ALA4848900

PubChem CID: 161810867

Max Phase: Preclinical

Molecular Formula: C24H25BrClNO5S

Molecular Weight: 554.89

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1cc(OCCCn2c(C)c(S(=O)(=O)c3ccc(Br)cc3)c(C)c2C(=O)O)cc(C)c1Cl

Standard InChI:  InChI=1S/C24H25BrClNO5S/c1-14-12-19(13-15(2)21(14)26)32-11-5-10-27-17(4)23(16(3)22(27)24(28)29)33(30,31)20-8-6-18(25)7-9-20/h6-9,12-13H,5,10-11H2,1-4H3,(H,28,29)

Standard InChI Key:  XTXZNIZKEYUMED-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
   12.4351  -26.4828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0267  -25.7702    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.6138  -26.4802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7332  -25.3426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4951  -25.6615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0330  -25.0358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6041  -24.3308    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8013  -24.5209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9223  -23.5696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4222  -22.9133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7404  -22.1521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2402  -21.4958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5585  -20.7378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3742  -20.6386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6925  -19.8815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1947  -19.2265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3754  -19.3323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0609  -20.0897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8741  -18.6772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5127  -18.4684    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   15.5111  -19.7781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8553  -25.1034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2081  -25.8492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3249  -24.4248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3044  -25.3744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2915  -24.5491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5688  -24.1526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8626  -24.5810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8837  -25.4102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6070  -25.8029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6848  -26.4645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1758  -23.9828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1386  -24.1854    0.0000 Br  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  2  0
  6  7  1  0
  7  8  1  0
  8  4  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 17 19  1  0
 16 20  1  0
 15 21  1  0
  6 22  1  0
 22 23  1  0
 22 24  2  0
  4  2  1  0
  2 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
  5 31  1  0
  8 32  1  0
 28 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4848900

   ---

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: 554.89

Molecular Weight (Monoisotopic): 553.0325

AlogP: 6.14

#Rotatable Bonds: 8

Polar Surface Area: 85.60

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.24

CX Basic pKa: ┄

CX LogP: 6.63

CX LogD: 3.19

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.34

Np Likeness Score: -1.19

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