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

ID: ALA1771518

PubChem CID: 53231752

Max Phase: Preclinical

Molecular Formula: C16H14Br2N2O4

Molecular Weight: 458.11

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C16H14Br2N2O4/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:  YSOCHEORPLYLDC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
   -2.5042    0.0875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8349    0.5700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0917    1.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9167    1.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1735    0.5700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4013    2.0259    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.9577    0.3139    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -1.1233    0.1524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1286   -0.6726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4062    0.5603    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3056    0.1432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0227    0.5511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7345    0.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7253   -0.6885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4363   -1.1055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1543   -0.6976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1570    0.1317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454    0.5450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8727    0.5421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5859    0.1276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8667   -1.1137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5833   -0.7048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2956   -1.1209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0042   -1.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  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
  2  3  2  0
 15 16  2  0
  2  8  1  0
 16 17  1  0
  1  2  1  0
 17 18  2  0
 18 13  1  0
  8  9  2  0
 17 19  1  0
  3  4  1  0
 19 20  1  0
  8 10  1  0
 16 21  1  0
  5  1  1  0
 21 22  1  0
 10 11  1  0
 22 23  1  0
 23 24  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA1771518

   4,5-dibromo-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: 458.11

Molecular Weight (Monoisotopic): 455.9320

AlogP: 3.42

#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: 11.57

CX Basic pKa: ┄

CX LogP: 3.07

CX LogD: 3.07

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.49

Np Likeness Score: -0.47

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