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

ID: ALA212723

Cas Number: 5987-00-8

PubChem CID: 668744

Max Phase: Preclinical

Molecular Formula: C13H13NO3

Molecular Weight: 231.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(C)n1-c1ccc(C(=O)O)c(O)c1

Standard InChI:  InChI=1S/C13H13NO3/c1-8-3-4-9(2)14(8)10-5-6-11(13(16)17)12(15)7-10/h3-7,15H,1-2H3,(H,16,17)

Standard InChI Key:  WAYCNXGAKFXIKA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 17 18  0  0  0  0  0  0  0  0999 V2000
   -2.9306   -3.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9318   -4.1107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2169   -4.5235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5005   -4.1102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5034   -3.2797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2187   -2.8705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7904   -2.8645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0744   -3.2743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7936   -2.0395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7854   -4.5216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6480   -4.5240    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4014   -4.1879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9539   -4.8006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5420   -5.5154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7349   -5.3444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1222   -5.8969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5723   -3.3808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7  9  2  0
  4  5  1  0
  4 10  1  0
 11 12  1  0
  2  3  1  0
  5  6  2  0
  6  1  1  0
  1  2  2  0
  5  7  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 11  1  0
  2 11  1  0
  3  4  2  0
 15 16  1  0
  7  8  1  0
 12 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA212723

   4-(2,5-dimethyl-1H-pyrrol-1-yl)-2-hydroxybenzoic 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: 231.25

Molecular Weight (Monoisotopic): 231.0895

AlogP: 2.50

#Rotatable Bonds: 2

Polar Surface Area: 62.46

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.38

CX Basic pKa: ┄

CX LogP: 3.34

CX LogD: -0.07

Aromatic Rings: 2

Heavy Atoms: 17

QED Weighted: 0.83

Np Likeness Score: -0.83

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. PubChem BioAssay data set, 

6. PubChem BioAssay data set, 

7. Patel RV, Park SW..  (2015)  Pyrroloaryls and pyrroloheteroaryls: Inhibitors of the HIV fusion/attachment, reverse transcriptase and integrase.,  23  (17): [PMID:26116177] [10.1016/j.bmc.2015.06.016]

8.  (2015)  Pyrrol-1-yl benzoic acid derivatives useful as myc inhibitors, 

Source

Source(3):

• Scientific Literature
• PubChem BioAssays
• Patent Bioactivity Data