4,5-Dichloro-1H-pyrrole-2-carboxylic acid(3-methoxy-4-prop-2-ynyloxy-benzyloxy)-amide

ID: ALA1770190

PubChem CID: 53231869

Max Phase: Preclinical

Molecular Formula: C16H14Cl2N2O4

Molecular Weight: 369.20

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#CCOc1ccc(CONC(=O)c2cc(Cl)c(Cl)[nH]2)cc1OC

Standard InChI:  InChI=1S/C16H14Cl2N2O4/c1-3-6-23-13-5-4-10(7-14(13)22-2)9-24-20-16(21)12-8-11(17)15(18)19-12/h1,4-5,7-8,19H,6,9H2,2H3,(H,20,21)

Standard InChI Key:  RDHCQEOAYHEBQM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
   -3.5875    0.5834    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9182    1.0658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1750    1.8541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0000    1.8541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2568    1.0658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2066    0.6482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2119   -0.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4895    1.0561    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7777    0.6391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0606    1.0470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6512    0.6299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6420   -0.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3529   -0.6097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3621    1.0408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0737    0.6275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0729   -0.2015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7889    1.0388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5026    0.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7855   -0.6171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5018   -0.2078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2145   -0.6234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9250   -1.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4847    2.5218    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.0410    0.8097    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
 11 12  2  0
  2  6  1  0
 12 13  1  0
 13 16  2  0
  4  5  2  0
 15 14  2  0
 14 11  1  0
 15 16  1  0
  6  7  2  0
  2  3  2  0
  6  8  1  0
 15 17  1  0
  1  2  1  0
 17 18  1  0
  8  9  1  0
 16 19  1  0
  3  4  1  0
 19 20  1  0
  9 10  1  0
 20 21  1  0
  5  1  1  0
 21 22  3  0
 10 11  1  0
  4 23  1  0
  5 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1770190

   4,5-dichloro-N-[(3-methoxy-4-prop-2-ynoxyphenyl)methoxy]-1H-pyrrole-2-carboxamide

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: 369.20

Molecular Weight (Monoisotopic): 368.0331

AlogP: 3.20

#Rotatable Bonds: 7

Polar Surface Area: 72.58

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.95

CX Basic pKa: ┄

CX LogP: 2.76

CX LogD: 2.76

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.58

Np Likeness Score: -1.01

References

1. Wang MZ, Xu H, Liu TW, Feng Q, Yu SJ, Wang SH, Li ZM..  (2011)  Design, synthesis and antifungal activities of novel pyrrole alkaloid analogs.,  46  (5): [PMID:21356570] [10.1016/j.ejmech.2011.01.031]

Source

Source(1):

• Scientific Literature