1H-Pyrrole-2-carboxylic acid(3-methoxy-4-prop-2-ynyloxy-benzyloxy)-amide

ID: ALA1770184

PubChem CID: 53231523

Max Phase: Preclinical

Molecular Formula: C16H16N2O4

Molecular Weight: 300.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#CCOc1ccc(CONC(=O)c2ccc[nH]2)cc1OC

Standard InChI:  InChI=1S/C16H16N2O4/c1-3-9-21-14-7-6-12(10-15(14)20-2)11-22-18-16(19)13-5-4-8-17-13/h1,4-8,10,17H,9,11H2,2H3,(H,18,19)

Standard InChI Key:  UMBNUQUZXGYVLJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
   -3.3042  -15.2916    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6349  -14.8092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8917  -14.0209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7167  -14.0209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9735  -14.8092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9233  -15.2268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9286  -16.0518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2062  -14.8189    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4944  -15.2359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2227  -14.8280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9345  -15.2451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9253  -16.0677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6363  -16.4847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6454  -14.8342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3570  -15.2475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3562  -16.0765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0722  -14.8362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7859  -15.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0689  -16.4921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7851  -16.0828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4978  -16.4984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2083  -16.9083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  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
M  END

Alternative Forms

1. Parent:

   

   ALA1770184

   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: 300.31

Molecular Weight (Monoisotopic): 300.1110

AlogP: 1.90

#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: 13.33

CX Basic pKa: ┄

CX LogP: 1.84

CX LogD: 1.84

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.60

Np Likeness Score: -1.07

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