4-(4-chlorophenethyl)-1H-pyrrole-2-carboxylic acid

ID: ALA453239

PubChem CID: 11299678

Max Phase: Preclinical

Molecular Formula: C13H12ClNO2

Molecular Weight: 249.70

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1cc(CCc2ccc(Cl)cc2)c[nH]1

Standard InChI:  InChI=1S/C13H12ClNO2/c14-11-5-3-9(4-6-11)1-2-10-7-12(13(16)17)15-8-10/h3-8,15H,1-2H2,(H,16,17)

Standard InChI Key:  JXYKONJPFAHRTG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 17 18  0  0  0  0  0  0  0  0999 V2000
   -4.9788   -2.8231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9802   -3.6508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2672   -4.0637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5479   -3.6502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5511   -2.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2691   -2.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6937   -2.4113    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.8330   -4.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1191   -3.6489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4042   -4.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3174   -4.8783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5104   -5.0490    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0984   -4.3342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6512   -3.7217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7243   -4.2471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2098   -4.9141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0590   -3.4932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0
  4  5  1  0
  9 10  1  0
 10 11  2  0
  2  3  1  0
  5  6  2  0
  6  1  1  0
  1  2  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 10  1  0
  1  7  1  0
  3  4  2  0
  4  8  1  0
 15 16  1  0
 15 17  2  0
 13 15  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA453239

   4-(4-chlorophenethyl)-1H-pyrrole-2-carboxylic 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: 249.70

Molecular Weight (Monoisotopic): 249.0557

AlogP: 3.15

#Rotatable Bonds: 4

Polar Surface Area: 53.09

Molecular Species: ACID

HBA: 1

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.61

CX Basic pKa: ┄

CX LogP: 3.77

CX LogD: 0.43

Aromatic Rings: 2

Heavy Atoms: 17

QED Weighted: 0.87

Np Likeness Score: -0.26

References

1. Sparey T, Abeywickrema P, Almond S, Brandon N, Byrne N, Campbell A, Hutson PH, Jacobson M, Jones B, Munshi S, Pascarella D, Pike A, Prasad GS, Sachs N, Sakatis M, Sardana V, Venkatraman S, Young MB..  (2008)  The discovery of fused pyrrole carboxylic acids as novel, potent D-amino acid oxidase (DAO) inhibitors.,  18  (11): [PMID:18455394] [10.1016/j.bmcl.2008.04.020]

2. Hopkins SC, Heffernan ML, Saraswat LD, Bowen CA, Melnick L, Hardy LW, Orsini MA, Allen MS, Koch P, Spear KL, Foglesong RJ, Soukri M, Chytil M, Fang QK, Jones SW, Varney MA, Panatier A, Oliet SH, Pollegioni L, Piubelli L, Molla G, Nardini M, Large TH..  (2013)  Structural, kinetic, and pharmacodynamic mechanisms of D-amino acid oxidase inhibition by small molecules.,  56  (9): [PMID:23631755] [10.1021/jm4002583]

Source

Source(1):

• Scientific Literature