3-Methoxy-2-{2-[(1H-pyrrole-2-carbonyl)-aminooxymethyl]-phenyl}-acrylic acid methyl ester

ID: ALA1770186

PubChem CID: 53231525

Max Phase: Preclinical

Molecular Formula: C17H18N2O5

Molecular Weight: 330.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CO/C=C(/C(=O)OC)c1ccccc1CONC(=O)c1ccc[nH]1

Standard InChI:  InChI=1S/C17H18N2O5/c1-22-11-14(17(21)23-2)13-7-4-3-6-12(13)10-24-19-16(20)15-8-5-9-18-15/h3-9,11,18H,10H2,1-2H3,(H,19,20)/b14-11+

Standard InChI Key:  IMEHAMQDZCBMBQ-SDNWHVSQSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
   -1.8375  -21.8750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1682  -21.3925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4250  -20.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2500  -20.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5068  -21.3925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4566  -21.8101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4619  -22.6351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2605  -21.4022    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9723  -21.8193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6894  -21.4114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4012  -21.8284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3920  -22.6510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1029  -23.0680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1121  -21.4175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8237  -21.8308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8229  -22.6598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1129  -20.5925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8278  -20.1808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3989  -20.1793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5419  -20.5940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2568  -20.1823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3998  -19.3543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6840  -20.5911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9700  -20.1778    0.0000 C   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
 14 17  1  0
  1  2  1  0
 17 18  2  0
  8  9  1  0
 17 19  1  0
  3  4  1  0
 18 20  1  0
  9 10  1  0
 20 21  1  0
  5  1  1  0
 19 22  2  0
 10 11  1  0
 19 23  1  0
 23 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1770186

   methyl (E)-3-methoxy-2-[2-[(1H-pyrrole-2-carbonylamino)oxymethyl]phenyl]prop-2-enoate

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: 330.34

Molecular Weight (Monoisotopic): 330.1216

AlogP: 2.04

#Rotatable Bonds: 7

Polar Surface Area: 89.65

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.33

CX Basic pKa: ┄

CX LogP: 2.05

CX LogD: 2.05

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.35

Np Likeness Score: -0.21

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