4-(3-acetyl-2,5-dimethyl-1H-pyrrol-1-yl)benzoic acid

ID: ALA3593489

Cas Number: 870540-39-9

PubChem CID: 16486808

Max Phase: Preclinical

Molecular Formula: C15H15NO3

Molecular Weight: 257.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)c1cc(C)n(-c2ccc(C(=O)O)cc2)c1C

Standard InChI:  InChI=1S/C15H15NO3/c1-9-8-14(11(3)17)10(2)16(9)13-6-4-12(5-7-13)15(18)19/h4-8H,1-3H3,(H,18,19)

Standard InChI Key:  KGJRYCFRNREEOJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 19 20  0  0  0  0  0  0  0  0999 V2000
    2.5973   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5956   -2.7031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6375   -0.9049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5987    1.5004    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7390    2.9810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2067    3.2905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9546    1.9903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9492    0.8772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8437    3.7801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1898   -0.2984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8211    4.6570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0149    4.7788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1190    5.6302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  2  7  2  0
  1  8  2  0
  1  9  1  0
  5 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 10  1  0
 11 15  1  0
 14 16  1  0
 12 17  1  0
 17 18  2  0
 17 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3593489

   4-(3-acetyl-2,5-dimethyl-1H-pyrrol-1-yl)benzoic 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: 257.29

Molecular Weight (Monoisotopic): 257.1052

AlogP: 2.99

#Rotatable Bonds: 3

Polar Surface Area: 59.30

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.63

CX Basic pKa: ┄

CX LogP: 2.55

CX LogD: -0.15

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.86

Np Likeness Score: -1.28

References

1. Berne S, Kovačič L, Sova M, Kraševec N, Gobec S, Križaj I, Komel R..  (2015)  Benzoic acid derivatives with improved antifungal activity: Design, synthesis, structure-activity relationship (SAR) and CYP53 docking studies.,  23  (15): [PMID:26154240] [10.1016/j.bmc.2015.06.042]

Source

Source(1):

• Scientific Literature