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

ID: ALA2272053

PubChem CID: 76330656

Max Phase: Preclinical

Molecular Formula: C22H31NO3

Molecular Weight: 357.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(C)c(C2=C(O)C(C)(C)N(OCC3CCCCC3)C2=O)c(C)c1

Standard InChI:  InChI=1S/C22H31NO3/c1-14-11-15(2)18(16(3)12-14)19-20(24)22(4,5)23(21(19)25)26-13-17-9-7-6-8-10-17/h11-12,17,24H,6-10,13H2,1-5H3

Standard InChI Key:  HPIXVYOHAZLVOB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   11.7387   -9.8649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6508   -9.0524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9912   -9.5348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4516  -12.3445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4505  -13.1640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1585  -13.5730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8682  -13.1636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8654  -12.3409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1568  -11.9356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7438  -11.9361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1583  -14.3902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5715  -11.9296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1543  -11.1185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8108  -10.6389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5560   -9.8624    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4887  -10.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5887  -10.8892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7129  -10.8997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0344   -9.1998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8516   -9.1988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2593   -8.4906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0746   -8.4916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4823   -7.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0763   -7.0779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2582   -7.0769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8460   -7.7855    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  1  0
 21 26  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2272053

   1-(Cyclohexylmethoxy)-4-hydroxy-5,5-dimethyl-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: 357.49

Molecular Weight (Monoisotopic): 357.2304

AlogP: 5.01

#Rotatable Bonds: 4

Polar Surface Area: 49.77

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.51

CX Basic pKa: ┄

CX LogP: 5.30

CX LogD: 5.27

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.82

Np Likeness Score: 0.09

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