1-Methyl-1H-pyrrole-2-carboxylic acid(3-methoxy-4-prop-2-ynyloxy-benzyloxy)-methyl-amide

ID: ALA1770194

PubChem CID: 53232243

Max Phase: Preclinical

Molecular Formula: C18H20N2O4

Molecular Weight: 328.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#CCOc1ccc(CON(C)C(=O)c2cccn2C)cc1OC

Standard InChI:  InChI=1S/C18H20N2O4/c1-5-11-23-16-9-8-14(12-17(16)22-4)13-24-20(3)18(21)15-7-6-10-19(15)2/h1,6-10,12H,11,13H2,2-4H3

Standard InChI Key:  UZVMQYHHPOYVRW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
   -3.7375  -11.0708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0682  -10.5883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3250   -9.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1500   -9.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4068  -10.5883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3566  -11.0059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3619  -11.8309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6395  -10.5980    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9277  -11.0151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2106  -10.6072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5012  -11.0243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4920  -11.8469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2029  -12.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2121  -10.6134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9237  -11.0266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9229  -11.8557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6342   -9.7730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6389  -10.6154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526  -11.0291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6355  -12.2713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3518  -11.8619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0645  -12.2776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7750  -12.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7375  -11.8958    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
  8 17  1  0
  1  2  1  0
 15 18  1  0
  8  9  1  0
 18 19  1  0
  3  4  1  0
 16 20  1  0
  9 10  1  0
 20 21  1  0
  5  1  1  0
 21 22  1  0
 10 11  1  0
 22 23  3  0
  1 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1770194

   N-[(3-methoxy-4-prop-2-ynoxyphenyl)methoxy]-N,1-dimethylpyrrole-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: 328.37

Molecular Weight (Monoisotopic): 328.1423

AlogP: 2.25

#Rotatable Bonds: 7

Polar Surface Area: 52.93

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.28

CX LogD: 2.28

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.58

Np Likeness Score: -1.14

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