2-(4-(2,5-dimethyl-1H-pyrrol-1-yl)phenylthio)acetic acid

ID: ALA386313

Cas Number: 131817-93-1

PubChem CID: 767163

Max Phase: Preclinical

Molecular Formula: C14H15NO2S

Molecular Weight: 261.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(C)n1-c1ccc(SCC(=O)O)cc1

Standard InChI:  InChI=1S/C14H15NO2S/c1-10-3-4-11(2)15(10)12-5-7-13(8-6-12)18-9-14(16)17/h3-8H,9H2,1-2H3,(H,16,17)

Standard InChI Key:  DASVXRJADIYRNJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 18 19  0  0  0  0  0  0  0  0999 V2000
   -2.2806   -7.4666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2818   -8.2940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5669   -8.7069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8505   -8.2935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8534   -7.4630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5687   -7.0539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9980   -8.7074    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7514   -8.3712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3039   -8.9839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8920   -9.6988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0849   -9.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4722  -10.0802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9223   -7.5641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1404   -7.0478    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.5756   -7.4576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2885   -7.0424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0045   -7.4522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2854   -6.2174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  7  1  0
  2  7  1  0
  5  6  2  0
 11 12  1  0
  6  1  1  0
  8 13  1  0
  7  8  1  0
  5 14  1  0
  1  2  2  0
 14 15  1  0
  3  4  2  0
 15 16  1  0
 16 17  1  0
  4  5  1  0
 16 18  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA386313

   {[4-(2,5-dimethyl-1H-pyrrol-1-yl)phenyl]sulfanyl}acetic acid

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: 261.35

Molecular Weight (Monoisotopic): 261.0823

AlogP: 3.27

#Rotatable Bonds: 4

Polar Surface Area: 42.23

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.96

CX Basic pKa: ┄

CX LogP: 3.13

CX LogD: -0.05

Aromatic Rings: 2

Heavy Atoms: 18

QED Weighted: 0.86

Np Likeness Score: -1.50

References

1. Schepetkin IA, Khlebnikov AI, Kirpotina LN, Quinn MT..  (2006)  Novel small-molecule inhibitors of anthrax lethal factor identified by high-throughput screening.,  49  (17): [PMID:16913712] [10.1021/jm0605132]

2. Aiello D, Barnes MH, Biswas EE, Biswas SB, Gu S, Williams JD, Bowlin TL, Moir DT..  (2009)  Discovery, characterization and comparison of inhibitors of Bacillus anthracis and Staphylococcus aureus replicative DNA helicases.,  17  (13): [PMID:19477652] [10.1016/j.bmc.2009.05.014]

3. Wu S, Vossius S, Rahmouni S, Miletic AV, Vang T, Vazquez-Rodriguez J, Cerignoli F, Arimura Y, Williams S, Hayes T, Moutschen M, Vasile S, Pellecchia M, Mustelin T, Tautz L..  (2009)  Multidentate small-molecule inhibitors of vaccinia H1-related (VHR) phosphatase decrease proliferation of cervix cancer cells.,  52  (21): [PMID:19888758] [10.1021/jm901016k]

4. PubChem BioAssay data set, 

5. Merk D, Grisoni F, Friedrich L, Gelzinyte E, Schneider G..  (2018)  Computer-Assisted Discovery of Retinoid X Receptor Modulating Natural Products and Isofunctional Mimetics.,  61  (12): [PMID:29901398] [10.1021/acs.jmedchem.8b00494]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays