4-hydroxy-3-mesityl-5,5-dimethyl-1-(prop-2-ynyloxy)-1H-pyrrol-2(5H)-one

ID: ALA2272051

PubChem CID: 76330655

Max Phase: Preclinical

Molecular Formula: C18H21NO3

Molecular Weight: 299.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#CCON1C(=O)C(c2c(C)cc(C)cc2C)=C(O)C1(C)C

Standard InChI:  InChI=1S/C18H21NO3/c1-7-8-22-19-17(21)15(16(20)18(19,5)6)14-12(3)9-11(2)10-13(14)4/h1,9-10,20H,8H2,2-6H3

Standard InChI Key:  OKQHJUQFZQYETK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
    2.4071   -9.9392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3192   -9.1267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6595   -9.6091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1200  -12.4188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1188  -13.2383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8269  -13.6473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5365  -13.2379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5337  -12.4152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8251  -12.0099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4122  -12.0104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8267  -14.4645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2399  -12.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8226  -11.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4792  -10.7132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2243   -9.9367    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1570  -10.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2571  -10.9635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3812  -10.9740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7027   -9.2741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5198   -9.2592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9139   -8.5402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3067   -7.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  1  3  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  4 10  1  0
  6 11  1  0
  8 12  1  0
  9 13  1  0
 13 14  1  0
 14 15  1  0
 15  1  1  0
  1 16  1  0
 16 13  2  0
 14 17  2  0
 16 18  1  0
 15 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA2272051

   4-Hydroxy-5,5-dimethyl-1-prop-2-ynoxy-3-(2,4,6-trimethylphenyl)pyrrol-2-one

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: 299.37

Molecular Weight (Monoisotopic): 299.1521

AlogP: 3.07

#Rotatable Bonds: 3

Polar Surface Area: 49.77

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.30

CX Basic pKa: ┄

CX LogP: 3.41

CX LogD: 3.36

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.87

Np Likeness Score: -0.04

References

1. Ito M, Okui H, Nakagawa H, Mio S, Kinoshita A, Obayashi T, Miura T, Nagai J, Yokoi S, Ichinose R, Tanaka K, Kodama S, Iwasaki T, Miyake T, Takashio M, Iwabuchi J..  (2002)  Synthesis and insecticidal activity of N-oxydihydropyrroles: 4-hydroxy-3-mesityl-5,5-dimethyl derivatives with various substituents at the 1-position.,  66  (11): [PMID:12506980] [10.1271/bbb.66.2406]

Source

Source(1):

• Scientific Literature