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

ID: ALA1770187

PubChem CID: 53231866

Max Phase: Preclinical

Molecular Formula: C16H13Br3N2O4

Molecular Weight: 537.00

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#CCOc1ccc(CONC(=O)c2[nH]c(Br)c(Br)c2Br)cc1OC

Standard InChI:  InChI=1S/C16H13Br3N2O4/c1-3-6-24-10-5-4-9(7-11(10)23-2)8-25-21-16(22)14-12(17)13(18)15(19)20-14/h1,4-5,7,20H,6,8H2,2H3,(H,21,22)

Standard InChI Key:  ZYGKLTXTNQOQAE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
    7.6792  -20.4083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3485  -19.9258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0917  -19.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2667  -19.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0099  -19.9258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7820  -18.4699    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    6.2256  -20.1819    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    9.0600  -20.3434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0548  -21.1684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7771  -19.9355    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4890  -20.3526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2061  -19.9447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9179  -20.3618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9086  -21.1844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6196  -21.6014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6288  -19.9509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3403  -20.3641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3396  -21.1932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5763  -18.4699    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   14.0555  -19.9529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7693  -20.3666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0522  -21.6088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7685  -21.1994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4811  -21.6151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1917  -22.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  6  1  0
 12 13  1  0
  4  5  2  0
 13 14  2  0
  5  7  1  0
 14 15  1  0
 15 18  2  0
  2  3  2  0
 17 16  2  0
 16 13  1  0
 17 18  1  0
  2  8  1  0
  1  2  1  0
  8  9  2  0
  3 19  1  0
  3  4  1  0
 17 20  1  0
  8 10  1  0
 20 21  1  0
  5  1  1  0
 18 22  1  0
 10 11  1  0
 22 23  1  0
 23 24  1  0
 11 12  1  0
 24 25  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA1770187

   3,4,5-tribromo-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: 537.00

Molecular Weight (Monoisotopic): 533.8425

AlogP: 4.18

#Rotatable Bonds: 7

Polar Surface Area: 72.58

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.29

CX Basic pKa: ┄

CX LogP: 3.84

CX LogD: 3.84

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.41

Np Likeness Score: -0.38

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