(1R,5R)-1-dodecanoyl-4-hydroxy-4-methyl-6-oxa-3-aza-bicyclo[3.1.0]hexan-2-one

ID: ALA478290

PubChem CID: 9972760

Max Phase: Preclinical

Molecular Formula: C17H29NO4

Molecular Weight: 311.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCC(=O)[C@]12O[C@H]1C(C)(O)NC2=O

Standard InChI:  InChI=1S/C17H29NO4/c1-3-4-5-6-7-8-9-10-11-12-13(19)17-14(22-17)16(2,21)18-15(17)20/h14,21H,3-12H2,1-2H3,(H,18,20)/t14-,16?,17-/m0/s1

Standard InChI Key:  BXGAZSQVWXQIBE-NZEUDUFCSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
    7.8888   -0.6139    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5625   -0.1377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2300   -0.1193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4921    0.6620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3167    0.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9112    1.3722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0311    1.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0344    1.8925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7448    0.6528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7907    1.1030    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4374    0.1280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7859   -0.8148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3437   -0.4029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4601    1.0638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1737    0.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8890    1.0610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6027    0.6471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3180    1.0582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0316    0.6443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7469    1.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4605    0.6414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1758    1.0525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8895    0.6386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3 11  1  0
  1  2  1  0
  3 12  1  0
  2 13  2  0
  2  5  1  0
  9 14  1  0
  4  3  1  0
 14 15  1  0
  5  7  1  1
 15 16  1  0
  3  1  1  0
 16 17  1  0
  7  8  2  0
 17 18  1  0
  5  4  1  0
 18 19  1  0
  7  9  1  0
 19 20  1  0
  6  5  1  0
 20 21  1  0
  4 10  1  1
 21 22  1  0
  4  6  1  0
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA478290

   (1R,5R)-1-dodecanoyl-4-hydroxy-4-methyl-6-oxa-3-azabicyclo[3.1.0]hexan-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: 311.42

Molecular Weight (Monoisotopic): 311.2097

AlogP: 2.45

#Rotatable Bonds: 11

Polar Surface Area: 78.93

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.29

CX Basic pKa: ┄

CX LogP: 3.72

CX LogD: 3.72

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.35

Np Likeness Score: 1.04

References

1. Kuramochi K, Yukizawa S, Ikeda S, Sunoki T, Arai S, Matsui R, Morita A, Mizushina Y, Sakaguchi K, Sugawara F, Ikekita M, Kobayashi S..  (2008)  Syntheses and applications of fluorescent and biotinylated epolactaene derivatives: Epolactaene and its derivative induce disulfide formation.,  16  (9): [PMID:18375133] [10.1016/j.bmc.2008.03.029]

2. Yoda T, Furuta M, Tsutsumi T, Ikeda S, Yukizawa S, Arai S, Morita A, Yamatoya K, Nakata K, Tomoshige S, Ohgane K, Furuyama Y, Sakaguchi K, Sugawara F, Kobayashi S, Ikekita M, Kuramochi K..  (2021)  Epo-C12 inhibits peroxiredoxin 1 peroxidase activity.,  41  [PMID:34015702] [10.1016/j.bmc.2021.116203]

Source

Source(1):

• Scientific Literature